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Holiday Homes near Portland Castle

Portland Castle Liberty Road, Castletown, DT5 1AZ, England
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    Travellers to Isle of Portland are booking April dates now. Secure your holiday rental today, and have the perfect trip.
    All 100 Rentals in Isle of Portland
    Traditional Welcoming Stone Farmhouse - Smugglers Haunt, Weymouth1 / 40
    (19)Very good
    3.6 kilometres from Portland Castle
    6 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Castle Cove View: private access to sandy beach1 / 19
    (18)Excellent
    3.4 kilometres from Portland Castle
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Number 81 / 22
    (31)Excellent
    4.0 kilometres from Portland Castle
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    65 Fortuneswell - 180° Sea Views from Balcony1 / 19
    (38)Excellent
    0.9 kilometres from Portland Castle
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Central Heating
    • Ocean Views
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2017
    This holiday house is lovely. On the isle of portland with beautiful views over the sea from a large balcony which can be accessed from the master bedroom or a door on the...
    Reviewed 7 June 2017
    We stayed as a family (3 couples and a teen) and there was plenty of space. The location is great. Beach is a good 'walk the dinner off' distance away. Pubs and shops nearby...
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    About this property
    A contemporary, spacious house with private off-road parking. Situated in a central position on the lower part of the island, makes it ideal for guests visiting the Weymouth and Portland National Sailing Academy or the Jurrassic Coastline. Ideal for small groups, couples and families - with...
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    Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Seagull Cottage1 / 20
    (16)Very good
    0.9 kilometres from Portland Castle
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Washer
    • Ocean Views
    • DVD Player
    • Central Heating
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    We had had a stressful autumn and needed a retreat to recharge and regroup. Seagull Cottage provided the perfect location in a quiet street at a quiet time of the year.Chesil...
    Reviewed 30 December 2017
    Stayed here with my partner and our 2 girls for Christmas 2017. From the minute we arrived we felt so at home. It is an absolute gem of a cottage and we were thrilled with every...
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    About this property
    Seagull Cottage is a lovely holiday house ideal for sailing, beach, and outdoor activity holidays in Portland. It is located just one mile from the Weymouth and Portland National Sailing Academy (WPNSA), the 2012 Olympic Sailing venue. Chesil beach is just a few minutes walk, with swimming and...
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    Isle of Portland, Dorset
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Pebble Reef1 / 21
    (19)Very good
    3.1 kilometres from Portland Castle
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Balcony
    • DVD Player
    • Grill
    • Central Heating
    • Wi-Fi
    • Terrace
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 August 2017
    We had a lovely week stay in pebble reef. Fantastic, modern cottage with ample space for us and our 4 children. Lovely big kitchen with everything you could need. The bedrooms...
    Reviewed 27 June 2017
    Had such a lovely time at Pebble Reef cottage, so beautiful and quaint. Such a shame we didn't spend long there. The Cottage was spotless and fully equipped. Would highly recommend
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    About this property
    Pebble Reef is a traditional Quarryman's Cottage, full of character but lovingly renovated to include all the modern comforts you need. The cottage sleeps up to six people in 3 comfortable bedrooms. Upstairs there's one double with en-suite shower room, a twin bedroom, and on the ground floor...
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    Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Hector our Family Holiday Cottage in Weymouth1 / 10
    (16)Excellent
    4.1 kilometres from Portland Castle
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Secure Parking
    • Wi-Fi
    • Central Heating
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 November 2017
    Stayed in Hector for the fourth time.It is so handy for Weymouth Everything you need for a home from home.Thank you David.
    Reviewed 5 September 2017
    I think that this is our 5th year in a row in Hector and it will definitely not be the last. My wife and I have been staying in Weymouth for about 20 years and stayed in a lot...
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    About this property
    Welcome to Hector is our family friendly luxury self catering self catering holiday cottage. Hector is located in a private gated mews behind Brewers Quay very near to the Weymouth harbour side and only a few minutes from the beach, making it ideal for walking to a local restaurant or around the...
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    Weymouth, Dorset
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Marina Place Weymouth1 / 15
    (1)Excellent
    4.9 kilometres from Portland Castle
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Waterfront
    • Terrace
    • Balcony
    • Washer
    • DVD Player
    • Central Heating
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    The location of this apartment is amazing, everything is literally on the doorstep, shops and beach are just minutes away. The apartment itself is really well equipped, with...
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    About this property
    Marina Place Weymouth Is a modern fully equipped apartment that we have just acquired & are now running it as a holiday let. We already run a popular holiday apartment named Seaside, in Weymouth and you can see our reviews already on TripAdvisor. The apartment Is on the 2nd floor over looking the...
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    Weymouth, Dorset
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.6 kilometres from Portland Castle
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lyndhurst is a four bedroomed house opposite Victoria Gardens and a short walk from Chesil Beach. Downstairs you will find two family rooms, one with a TV and the other for quiet moments. The kitchen, which overlooks the outside decking area, is spacious and sports a large dining table - ideal...
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    Isle of Portland, Dorset
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
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    BEAUTIFUL STUDIO APARTMENT - OCEAN VIEWS,PORTLAND1 / 31
    (29)Very good
    4.3 kilometres from Portland Castle
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • DVD Player
    • Wi-Fi
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 December 2017
    Lovely, clean apartment within a quirky building, the coast path is on the doorstep and a 11 mile walk around this Island is a must for any walker, quarry's, lighthouses...
    Reviewed 8 September 2017
    My boyfriend and I have just returned from a lovely stay in Dorset. It was our first time to the area, which we found quiet, friendly and beautiful to look at. The weather was...
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    About this property
    A VERY MODERN HOLIDAY LET STUDIO APARTMENT LOCATED IN A QUIET POSITION ON THE ISLE OF PORTLAND NEAR WEYMOUTH IN THE HEART OF DORSET, ON THE COAST OF SOUTH WEST ENGLAND. SUITABLE FOR SINGLE OR DOUBLE OCCUPANCY. FACILITIES INCLUDE FLAT SCREEN TV, DVD PLAYER, MICROWAVE, MINI OVEN/GRILL, FRIDGE,...
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    Isle of Portland, Dorset
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Fishermans Cottage1 / 38
    (21)Very good
    4.1 kilometres from Portland Castle
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Central Heating
    • DVD Player
    • Ocean Views
    • Hot Tub
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    We had a lovely 4 night break in this cosy cottage. The weather was particularly cold so it was nice to be staying in such a comfortable home for the week with the hot tub as an...
    Reviewed 8 May 2017
    We spent a week here in March and although the weather was changeable we had a lovely time. The location is great for some lovely walks around Portland and the pub up the road...
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    About this property
    Fishermans Cottage is a charming detached 18th century cottage on the edge of Southwell, with excellent sea views. Recently renovated with full central heating throughout and Wi Fi. On the ground floor there is a lounge / diner with sea view, a reception room, a fully equipped kitchen, a...
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    Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Ocean House 80 yds from beach 4 Bed, 4 Bath, 4star1 / 19
    (6)Very good
    4.5 kilometres from Portland Castle
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Outdoor Dining Area
    • Washer
    • Central Heating
    • Cable/satellite TV
    • DVD Player
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 September 2017
    House was situated close to sea front, shops and harbour. Unfortunately it was also easily accessible by the nightly drunks who wondered up and down at all times of the night...
    Reviewed 11 October 2016
    This was my 2nd stay in Ocean House, and I still stand by my 1st review of this house... it's so homely and comfortable. It's been a full year sincel I was last there and it's...
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    About this property
    Ocean House is a 4 bedroom town house situated in the heart of the seaside town of Weymouth. The property has just been totally renovated throughout. The property has a wifi throughout, with all rooms having SMART TV's, full sky package. On the ground floor the property has Lounge, dining room,...
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    Weymouth, Dorset
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Tides1 / 25
    (43)Excellent
    4.0 kilometres from Portland Castle
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Parking
    • Private Garden
    • Wi-Fi
    • Central Heating
    • Ocean Views
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 November 2017
    We had a lovely time in Weymouth and the house was in a great location close to the harbour. Very clean throughout. Had a bit of trouble with the electric hobs but guides to how...
    Reviewed 2 November 2017
    Could not fault this trip, house and location were perfect for us, we will be back for sure.Thanks for sharing your lovely home.
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    About this property
    Tides is a modern well appointed property located at the end of a quiet cul-de-sac and has the advantage of overlooking the picturesque bay and sailing venue used for the 2012 Olympic Games. The house is situated at the beginning of the wonderful promenade that winds around Newtons Cove and on...
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    Weymouth, Dorset
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Chesil Holiday Lodge, Weymouth1 / 24
    (5)Excellent
    2.9 kilometres from Portland Castle
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Washer
    • Balcony
    • Sauna
    • Ocean Views
    • Wi-Fi
    • Parking
    • Shared Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 April 2017
    As soon as you open the door to the lodge you will experience the " Wow Factor ".The lodge is in a stunning and quiet position of the park facing the fleet lagoon. It...
    Reviewed 5 July 2016
    We had a lovely time at the lodge, really comfortable, modern and clean. Kate (the owner) was helpful and quick to respond to questions. Would recommend for a lovely family...
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    About this property
    A luxury 2 bedroom (sleeps 6) holiday lodge situated on the 5 star Chesil Vista Holiday Park, near Portland and Weymouth Dorset. The lodge is located near the coastal path and has elevated sea views directly over Chesil Beach and Fleet Lagoon. Guests can make use of the park facilities (Apr -...
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    Weymouth, Dorset
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pebble View1 / 9
    (18)Very good
    0.7 kilometres from Portland Castle
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Central Heating
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 August 2017
    Had a great family holiday staying here. Was quiet and relaxing very friendly people found everything that we needed in pebble view fab views from the upstairs rooms plenty of...
    Reviewed 14 July 2017
    Located in the interesting but slightly down at heel town of Fortuneswell. Very convenient for the National Sailing Centre, which was the base for our boat. Property...
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    About this property
    Pebbles view is a Victorian Portland stone built mid terrace cottage in the village of Fortuneswell Portland offering stunning panoramic sea views of the Jurassic coasts Chesil beach from all floors The newly refurbished cottage arranged over three floors comprises of the lounge with wooden...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Marina Bay View Apartment - Portland Harbour1 / 15
    (2)Excellent
    0.1 kilometres from Portland Castle
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Indoor Pool
    • Balcony
    • Parking
    • Sauna
    • Hot Tub
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 December 2016
    Easy booking process. Estate agents very friendly and answered all questions quickly.Directions to the apartment and getting the keys made the checkin process easy.Apartment...
    Reviewed 30 August 2016
    My husband and I stayed here for a week in August with a five year old and a 21 month old. The apartment was very clean and had great facilities. The kitchen had almost...
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    About this property
    Marina View Apartment is a stunning modern apartment located overlooking Portland Marina and Harbour on the Isle of Portland, Dorset. The modern accommodation on two floors is well presented and offers three spacious bedrooms. Use of indoor pool and great as a base for water sports or fishing....
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    Isle of Portland, Dorset
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Quarries Reach, rural & sea views Portland, Dorset1 / 17
    (50)Excellent
    3.9 kilometres from Portland Castle
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Central Heating
    • DVD Player
    • Ocean Views
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 December 2017
    Quarries Reach was a great house for three generations of our family to gather pre-Christmas to visit local relatives. Clean and comfortable, good kitchen facilities and plenty...
    Reviewed 7 December 2017
    The stay at quarries reach was quite nice : Deborah was really flexible and the house is very convenient for a stay with 10 people.
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    About this property
    Ideal for small groups, couples & families - fabulous rural and sea views. A contemporary spacious detached house with a safe, secluded and walled garden. Situated in a prime position with spectacular rural and sea views looking towards Dorset's Jurassic Coast. Sleeps up to 8 +2 comfortably in...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Sky View1 / 23
    (19)Excellent
    4.5 kilometres from Portland Castle
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Parking
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 October 2017
    We stayed at Sky View in September 2017 and had a fantastic time. The information pack that Martyn has put together about the accommodation and the surrounding area is excellent...
    Reviewed 3 June 2017
    Had the loveliest time staying here with my daughter and 3 young children. The flat has everything you need and more. Would highly recommend and hope to come back next year.
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    About this property
    Well equipped quirky town-centre flat in Weymouth, Dorset.Modern, bright and airy top floor flat. Hall, two double bedrooms, spacious lounge/diner with TV/DVD player, well equipped kitchen with full sized oven, dishwasher, fridge, combi microwave, toaster, coffee maker etc. Large modern bathroom...
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    Weymouth, Dorset
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Rosa Cottage1 / 29
    (32)Very good
    1.0 kilometres from Portland Castle
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Balcony
    • Wi-Fi
    • Washer
    • DVD Player
    • Central Heating
    • Terrace
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 January 2018
    My family stayed here over Xmas. I had been advised that it had been nicely festively decorated. The result a fiberoptic Christmas tree and a few small objects. Which was...
    Reviewed 20 August 2017
    Lovely cottage, warm and welcoming in style with all necessary amenities for a comfortable relaxed stay. Plenty of space for our family, generous sofas in lounge and comfy beds...
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    About this property
    A beautiful restored Victorian terraced cottage, on a quiet street in the village of Fortuneswell on the Isle of Portland, only 5 minutes walk from the famous Chesil Beach and part of Dorset's glorious Jurassic Coast. 5 min drive from National Sailing Academy. This former bakery has been lovingly...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    0.7 kilometres from Portland Castle
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Washer
    • Patio
    • Private Garden
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely holiday home sits in the heart of Fortuneswell, Portland a short stroll from the Jurassic Coast. Sea views can be seen from the property where in the evening the rear windows provide lovely sunset viewing. The owners of the property have made this holiday property a home and offers...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Weymouth Family Caravan 2018 Prestige Bordeaux1 / 23
    (13)Excellent
    4.8 kilometres from Portland Castle
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Shared Indoor Pool
    • DVD Player
    • Balcony
    • Grill
    • Central Heating
    • Patio
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 August 2017
    We were absolutely delighted to arrive at such a beautifully clean, homely caravan. The welcome pack left for us was a really lovely gesture. The caravan was so well equipped it...
    Reviewed 13 June 2017
    Very comfortable caravan, extremely clean and well looked after. The owners went out of their way to ensure we had a wonderful stay. It's in a great location with wonderful...
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    About this property
    Our brand new Swift Bordeaux prestige caravan sleeps 6 to a high degree of luxury, it is double glazed and centrally heated so why not stay for early or late season breaks as well as that restful time during the summer. Located with amazing views over Chesil Beach and Lyme Bay to east Devon. The...
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    Chickerell, Weymouth
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Two bedroom holiday bungalow1 / 8
    (10)Very good
    3.4 kilometres from Portland Castle
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2017
    Had a lovely two weeks, Bungalow was beautiful and clean with a great view of the sea. The owner Lesley gave us a nice welcome with some lovely flowers and milk etc and was very...
    Reviewed 17 July 2016
    The property has a partial view of the English channel from it's high vantage point. It was clean & tidy. The owner was very pleasant & helpful at handover.It is described...
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    About this property
    A comfortable terraced bungalow with lounge/diner, kitchen and patio area in grounds near to Pennsylvania Castle so ideal for anyone attending functions there. Portland is a nature lovers paradise particularly of interest to birdwatching enthusiasts also to sailors as the National Sailing Academy...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 The Old Police Station1 / 17
    (6)Excellent
    0.5 kilometres from Portland Castle
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Private Garden
    • Wi-Fi
    • Ocean Views
    • Grill
    • DVD Player
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 September 2017
    Lovely holiday home, really well equipped and very spacious. Only thing missing was a washing machine. Location close to the beach, Weymouth and many places to visit.
    Reviewed 1 January 2017
    The property was as described and larger than anticipated. Although there is a designated car parking space behind the property, we managed to park on the road outside the...
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    About this property
    A beautifully presented character house with views over Chesil Beach and Portland Harbour. This holiday home has many character features and really is a home from home. The property has a single parking space, there is also ample on road parking and a covered 'alfresco dining' seating area. A...
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    Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Meadow View located in Weymouth, Dorset1 / 15
    (1)Excellent
    3.4 kilometres from Portland Castle
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 August 2014
    Fantastic house not far from Weymouth town centre (5 min car drive ) and close to local shops in Wyke Regis >(newsagent,petrol,food shops ) We stayed here for one week and...
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    About this property
    Nestled away between Weymouth and Portland, the village of Wyke Regis provides the perfect position to explore the Jurassic coastline. Located at the south-eastern end of Chesil Beach, the village is also just a short drive from the market town of Dorchester. Located in a quiet residential area,...
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    Location Information
    Weymouth, Dorset
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    0.6 kilometres from Portland Castle
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Central Heating
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely holiday home sits in the heart of Fortuneswell, Portland a short stroll from Chesil Cove. Sea views can be seen from the property where in the evening the rear windows provide lovely sunset viewing. The owners of the property have made this holiday property a home and it offers...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Mermaid Cottage1 / 8
    (1)Excellent
    3.1 kilometres from Portland Castle
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • DVD Player
    • Private Garden
    • Washer
    • Central Heating
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 August 2017
    Our family all had a brilliant holiday, cottage comfortable, with everything we needed. Even a play room for the kids, trampoline & swings in the garden.No do's and dont's...
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    About this property
    Whether you are looking for that relaxing break, or here to sail or just time with the family this charming cottage would suit your needs. Nestled off Wakeham, you will agree this cottage is a real find. A charming cottage nestled just behind Wakeham, backing on to open land. This spacious...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Haven holiday Weymouth Bay mobile home (sleeps 8)1 / 9
    (5)Very good
    1.5 kilometres from Portland Castle
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Parking
    • Shared Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 June 2017
    we arrived and found mobile holiday caravan in clean and good condition. instructions were how to find the site were good and helpful we had a nice stay. looking forward to our...
    Reviewed 22 September 2016
    Really enjoyed our stay. Caravan very clean and well maintained. On lovely site. So all good. Owner very nice in her communications. Good value. Great area and coastline to...
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    About this property
    We are delighted to offer the rental of our well-presented and modern holiday home which is situated in the prestigious resort of Weymouth Bay in Dorset. The caravan itself is situated merely 3 minutes walk from the resort facilites complex giving great freedom for coming and going. The caravan...
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    Location Information
    Weymouth, Dorset
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    CARAVAN - WEYMOUTH1 / 4
    (2)Excellent
    4.2 kilometres from Portland Castle
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our caravan is a bright and airy Wiilerby Eco Salsa. It is decorated and furnished to a good standard and can sleep up to 8 guests a double master bedroom plus 2 twin bedrooms sleeping 2 people in each. In addition there is a double bed settee in the lounge. Outside there are chairs and a table on...
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    Location Information
    Weymouth, Dorset
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Artist Cottage1 / 12
    (4)Very good
    0.8 kilometres from Portland Castle
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Shared Garden
    • Balcony
    • Ocean Views
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 April 2017
    We stayed with friends on New Years Eve in this beautiful terraced cottage. The experience was amazing: Portland Bill seems to exist in a time warp and I will always remember...
    Reviewed 31 March 2017
    We have stayed here 3 or 4 times and always had a lovely time. The house is a very pretty old traditional Portland Stone building. It is in a no through road so very quiet...
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    About this property
    Built in the 1800's, this sweet little original Portland stone Fisherman's cottage promises a lovely holiday experience.Artist Cottage sleeps four people in two bedrooms and has been delightfully restored.The cottage is found in Fortuneswell just five minutes from the National Sailing Academy and a...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Chesil View House located in Portland, Dorset1 / 15
    (2)Very good
    1.1 kilometres from Portland Castle
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 August 2017
    Just back from a lovely week here. The house is beautiful and the views from the top floor are amazing. Yes it's on a steep hill but so are most houses on Portland! Parking...
    Reviewed 18 January 2017
    The little house on St Martins Road is very sweet. It is on a tremendous hill and parking can be a problem but once inside it is very well appointed. The living/dining room is a...
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    About this property
    Chesil View House offers stylish accommodation that was originally a fisherman's cottage in the beautiful village of Fortuneswell, nestled amongst the hills of Portland. Internally the property is furnished to a high standard with spectacular views from the top of the house of Chesil Beach, Lyme...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Chiswell Cottage1 / 12
    (9)Excellent
    0.6 kilometres from Portland Castle
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 September 2016
    The house looked good inside and was nicely decorated and well equipped in terms of crockery, glasses etc. On arrival at the house the bin was overflowing and the door and...
    Reviewed 20 August 2016
    We spent a week at Chiswell cottage, was exactly as we expected. There were 6 adults, 2 children and a toddler and we had plenty of room. The kitchen was brilliant with both a...
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    About this property
    A spacious, comfortable cottage in this pretty road, a short walk down to Chesil Beach and Cove, and being in a convenient position for The National Sailing Academy and Portland Harbour. A four bedroom cottage over three floors with views over Chesil Beach. There is a private, fully enclosed rear...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.1 kilometres from Portland Castle
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean Views is perched in an enviable position on Portland's seafront, on the Jurassic coast beside Chesil Beach. The Olympus Penthouse is a two bedroom, fifth floor apartment with superb views over the Dorset coastline, Portland Marina, the National Sailing Academy and Portland Castle, built by...
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    Location Information
    Isle of Portland, Dorset
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    The Gift House, a historic Seaman's Chaplaincy1 / 22
    (3)Very good
    0.3 kilometres from Portland Castle
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Cable/satellite TV
    • Private Garden
    • Central Heating
    • Ocean Views
    • Wi-Fi
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 January 2018
    We stayed at the Gift House over Christmas / New Year and enjoyed staying, the accommodation was well equipped and generally well maintained.Our party consisted of two...
    Reviewed 28 September 2017
    We stayed at The Gift House for 4 nights last week and loved the house so much! It has everything you could need and is really nicely decorated with lots of quirky additions...
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    About this property
    The house is a late Georgian stone house located in the middle of island village, facing the sea. All 4 double bedrooms, the lounge and dining room are having panoramic sea view. The house is fully equipped self catering and has everything you need for an unforgettable holiday. The house has...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Pitt Hayes Cottage1 / 28
    (10)Very good
    1.3 kilometres from Portland Castle
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Wi-Fi
    • Ocean Views
    • Parking
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 August 2016
    Stunning views, flowers, tea, coffee and biscuits awaiting us. Cottage clean and well maintained and the Red House letting agents attended promptly when we had wifi problems...
    Reviewed 9 June 2016
    We recently stayed here as a large family to celebrate my mother in laws 80th birthday who was born and raised in Portland. It was important for me to find suitable...
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    About this property
    This well presented holiday house has a large and sociable open plan living area with kitchen, seating and dining areas, allowing for a relaxed and inclusive holiday atmosphere. There are four bedrooms, a bathroom and a shower room. The ground floor provides two twin rooms and a shower room with a...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Cove Park1 / 14
    (3)Very good
    3.4 kilometres from Portland Castle
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • DVD Player
    • Central Heating
    • Ocean Views
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 December 2017
    Just leaving Portland after having a smashing Christmas and break at this delightful bungalow. It was just perfect for myself and my mum. So warm and cosy and very well equipped...
    Reviewed 30 June 2017
    Had a great stay in this lovely bungalow. Lots of home comforts and the kitchen was well equipped.Home from home. Loved the view from the veranda and the dogs enjoyed the garden.
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    About this property
    PET Friendly! A two-bedroom bungalow set in a unique coastal park offering total relaxation and fantastic sea views. The site is ideal for a place to rest your head after a day on the water or if you are looking for a relaxing quiet break by the sea. This holiday home features all the essentials...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Littlecot located in Weymouth, Dorset1 / 72
    (14)Very good
    2.8 kilometres from Portland Castle
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 September 2017
    Have just returned from an amazing family weekend. The owners were extremely helpful on the phonecall a few days before with lots of information. The weekend away was for all...
    Reviewed 24 May 2017
    We all had a wonderful weekend break at Littlecot. The house had everything we needed and gave us a great base to explore Weymouth and Portland The house is tastefully decorated...
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    About this property
    Littlecot is a four bedroom cottage, set over three floors. Furnished caringly throughout with finishing touches from Laura Ashley and some rooms boasting sea views of Portland Harbour, Chesil Beach and The World Heritage Status Jurassic Coastline. Internally, the tasteful decoration complete with...
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    Location Information
    Weymouth, Dorset
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Park Mews located in Weymouth, Dorset1 / 10
    (5)Very good
    5.0 kilometres from Portland Castle
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 October 2017
    We found the place to park our car in swag lane and it in small car park you have to turn in too. Them we went out of car park and turned right and walk a bit to where we came...
    Reviewed 19 September 2017
    Really nice property.A very handy location for visiting Weymouth .Great to have private parking too.
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    About this property
    Park Mews is a contemporary, mews style semi-detached two story house located in Weymouth town centre, just minutes from the beach. Internally, the property is furnished to a high standard throughout. Externally, the furnished patio area at the front of the property is ideal for relaxing after a...
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    Location Information
    Weymouth, Dorset
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Nothe View located in Weymouth, Dorset1 / 32
    (4)Very good
    4.2 kilometres from Portland Castle
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 June 2017
    Booked this for 4 adults, two teenagers and a four year old. The accommodation is split over three floors which you get used to. Bedrooms are on the ground and first floor and...
    Reviewed 3 June 2015
    Great location for Harbour and beach being walking distance even for young children. Plenty of places to eat and drink. Park close by for the children to burn off a little...
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    About this property
    Nothe View is a spacious four bedroom townhouse set over three storeys. Situated within the Admirals Quarter development, Nothe View perfectly combines contemporary comfort and design with environmental sensitivity. Internally, the property is finished to a high standard and boasts glimpses of...
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    Location Information
    Weymouth, Dorset
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Casita del mar1 / 11
    (1)Excellent
    0.8 kilometres from Portland Castle
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Ocean Views
    • Grill
    • Balcony
    • Washer
    • DVD Player
    • Terrace
    • Central Heating
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 2017
    This cottage suited our family needs perfectly as we were able to bring our very well behaved dog with us! Susan was so helpful and ensured we were well informed about the...
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    About this property
    150 Year Old Portland Stone Fisherman's Cottage. Two leather sofas to seat six. Freeview T.V. Books. DVD's. C.D's. Games .Wifi. There is a wood burning stove for the winter months and barbeque and alfresco dining during the summer months. Vintage pine dining table and chairs to seat six. A...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Apartment 3, Catherine House located in Weymouth, Dorset1 / 8
    (2)Excellent
    4.5 kilometres from Portland Castle
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 June 2017
    Thank you so much for helping to make our holiday a wonderful time with loads of new memories x you have a gorgeous apartment so clean, comfortable and very nicely decorated...
    Reviewed 28 August 2016
    This is Mr Fuller and this was my first trip to Weymouth. Rarely if ever have I walked into an apartment and felt so instantly relaxed and at home. It is quiet, comfortable...
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    About this property
    3 Catherine House is located in the centre of Weymouth, home to a fine selection of eateries, bars, restaurants and shops whilst the esplanade, attractions and beach are a short walk away. This apartment is rear facing, away from the bustle of the high street. Internally, this modern first floor...
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    Location Information
    Weymouth, Dorset
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Shearwater located in Portland, Dorset1 / 16
    (3)Excellent
    3.2 kilometres from Portland Castle
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 January 2014
    We rented this house for a family holiday in October 2013, and couldn't of been happier with the accommodation.The house was clean, well laid out and had everything you could...
    Reviewed 13 May 2013
    Found the property to be very clean and beautifully decorated. The kitchen had everything you needed down to washing up liquid to tin foil and cling film. There was a brochure...
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    About this property
    Shearwater is a newly built three bedroom house, set over three floors, designed by an award-winning team and located on the east coast of Portland. It offers superb views of Pennsylvania Castle and out to the sea. The property is a highly energy efficient ‘Passivhaus’ eco-home, operating on a low...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Elizabethan House located in Portland, Dorset1 / 48
    (3)Average
    0.8 kilometres from Portland Castle
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 October 2017
    The house was perfect for our visit, everything we needed. Close to the beach and also local pub. The dogs enjoyed it too!
    Reviewed 7 August 2015
    This is a pleasant property with plenty of space. The lounge/dining room was welcoming and comfortable and it has possibly the best equipped kitchen I have had in a rented...
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    About this property
    Elizabethan House is 17th Century Grade II listed property located in Portland, situated just 500 yards from Chesil Beach and within a short walk from the National Sailing Academy. Internally, the property has been refurbished whilst retaining a character style with exposed stone walls, stripped...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    9 Sidon Mews located in Portland, Dorset1 / 24
    (1)Excellent
    0.3 kilometres from Portland Castle
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 January 2018
    Fantastic location in easy walking distance to the beach. Had a great NY break and would certainly return to this property if staying in Portland again. House is very...
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    About this property
    When you're looking for an escape with the beauty of Portland Harbour on your doorstep, look no further that 9 Sidon Mews. With stylish and modern interiors and a bright and sunny garden, you will find plenty of space for everybody to unwind. This contemporary house is especially well suited to...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Weymouth Harbour View1 / 31
    (16)Excellent
    4.3 kilometres from Portland Castle
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
    • Waterfront
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 August 2017
    Totally love this house - 2 years now - would love to make it 3 in 2018Fantastic vibeLove sitting in the main first floor watching the harbour life
    Reviewed 16 July 2017
    A wonderfully rustic cottage in a fabulous location on the harbour. The cottage is over 3 floors so there is plenty of room to spread out.The kitchen had every comfort of home...
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    About this property
    Booking fee included in Price with Weymouth Harbour View! Video Tour: https://youtu.be/sWvEXoH02p4 32' Smart LCD TV's IN ALL BEDROOMS WITH SKY MOVIES AND FIBRE BROADBAND!!! LOCATION Directly on Weymouth's Old Harbour this 200 year old character house with uninterrupted views towards the...
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    Location Information
    Weymouth, Dorset
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    82 Ocean Views located in Portland, Dorset1 / 16
    (5)Very good
    0.1 kilometres from Portland Castle
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 February 2017
    Stayed here for half term with wife and two children. Was perfect for what we were after. Bright modern apartment which was well kitted out. Excellent indoor communal pool...
    Reviewed 25 August 2016
    Stayed with family in August 2016 after booking through Blue Chip Holidays.Lovely apartment. Very comfortable and has large balcony which runs across its full width. Two...
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    About this property
    82 Ocean Views is a stylishly furnished apartment with partial sea views, located on the fourth floor of the development, in an enviable position on Portland's seafront. The apartment has been finished to the highest standard with high quality flooring and polished granite worktops exemplifying the...
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    Location Information
    Isle of Portland, Dorset
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.9 kilometres from Portland Castle
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Central Heating
    • Ocean Views
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wavecrest is in the village of Fortuneswell, overlooking Chesil Beach and close to the Weymouth and Portland Sailing Academy and Windsurfing Centre. Perfectly located for sailors, windsurfers, divers, walkers and cyclists with storage for boards, sails, bikes and wetsuits as well as a 72 hour free...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Sea Pinks Cottage located in Portland, Dorset1 / 13
    (3)Average
    0.8 kilometres from Portland Castle
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 April 2017
    This booking was made on behalf of my daughter and her young family, and friends of hers. The owner was very helpful when I was making the arrangements. Overall my family were...
    Reviewed 8 November 2016
    Upon arrival we weren't overly surprised at the lack of parking in Mallams. It is very narrow. Yes, you can stop in the vicinity to unload, but then have to drive down to a free...
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    About this property
    Sea Pinks Cottage was built around 1860 and is a fine example of a traditional fisherman's cottage built with Portland stone. The property has been refurbished to a high standard with the bedrooms offering views either towards Portland, Lyme Bay or Chesil Beach. Externally, the property boasts a...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    167 Ocean Views located in Portland, Dorset1 / 19
    (1)Excellent
    0.1 kilometres from Portland Castle
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 June 2014
    Our apartment was clean, modern and welcoming. We were pleasantly surprised at the size of the rooms and the view of the hills was beautiful. Seagulls constantly squawking...
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    About this property
    Set on the fourth floor of the Ocean Views development, 167 Ocean Views is a contemporary apartment with a bright, spacious feel throughout. Open plan living means it's easy to unwind in style when you're not out exploring the nearby Jurassic Coast, and you can step from the living space onto your...
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    Location Information
    Isle of Portland, Dorset
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Sea Cat1 / 15
    (1)Excellent
    1.0 kilometres from Portland Castle
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Central Heating
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 September 2015
    The apartment was a little hard to find, but we liked the neighborhood from the first moment. The view is incredible! When we sat foot into the apartment we had the pleasure to...
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    About this property
    A charming Portland Stone Cottage in the heart of Fortuneswell. Tastefully decorated and furnished it offers cosy accommodation, for four people. Public parking close by and you are just a short stroll from Chesil Beach, if you turn in the other direction and head up the hill you will arrive at the...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    105 Ocean Views located in Portland, Dorset1 / 18
    (9)Very good
    0.1 kilometres from Portland Castle
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 January 2018
    We have stayed here before but will not be staying again. We could not park as someone was always in our place we kept phoning Blue Chip Holidays who were very sorry but...
    Reviewed 1 November 2016
    This fifth floor flat has a clean, smart and modern feel. Pretty much everything you need is already there in the cupboards, the only problem was that we struggled to find out...
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    About this property
    Situated on Portland's scenic seafront with the famous Chesil Beach almost on your doorstep is 105 Ocean Views, a contemporary and stylish two bedroom apartment. With sophisticated furnishings and plenty of space for a group of four, this will make a wonderful getaway for a family or a group of...
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    Location Information
    Isle of Portland, Dorset
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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