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Isle of Portland Cottages

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    Travellers to Isle of Portland are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    28 Matching Rentals in Isle of PortlandView all 57 rentals
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    Fishermans Cottage1 / 42
    (28)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pebble Reef1 / 21
    (24)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Rosa Cottage1 / 30
    (34)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Schooner Cottage - At Christmas1 / 42
    (9)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Wi-Fi
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 September 2018
    Schooner cottage has been beautifully restored, giving it the character of its Georgian past with modern amenities.My husband and I stayed on Portland for 4 nights.. The views...
    Reviewed 22 August 2018
    This was our first visit to Portland and we had a brilliant stay. Our base was Schooner Cottage, a very quaint, very old fisherman's cottage which has been renovated to the...
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    About this property
    Schooner Cottage is a carefully restored Georgian fisherman’s house, located in Fortunes Well, Portland, Dorset. The cottage will offer you a relaxing wintertime retreat with a Danish hygge feel, where you can be cosy in front of a log burning stove. You will hear the westerly storm rage outside,...
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    Isle of Portland, Dorset DT5 1NH
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Portland Hideaway1 / 8
    (11)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Parking
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 September 2018
    Great place to stay in, clean and everything you need like home from home,the area is lovely and bus service is exceptional had a great time.
    Reviewed 26 August 2017
    Comfortable and surprisingly spacious, kitchen adequately equipped, owners next door but very low profile.The Hideaway is a conservatory and therefore does get very warm...
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    About this property
    The Portland Hideaway is a 4* self contained self catering unit with open plan living space.It benefits from a fully equipped kitchen,separate shower room with wc & sink,open plan bedroom/lounge area with ample seating on the reclining leather sofa's & air conditioning unit for your comfort....
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    Isle of Portland, Dorset DT5 2DS
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Artist Cottage - Charming coastal cottage on Portland :-)1 / 12
    (4)Very good
    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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    Isle of Portland, Dorset DT5 1NQ
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Dory Cottage1 / 20
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Private Garden
    • Patio
    • Ocean Views
    • Wi-Fi
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 October 2018
    The cottage was very lovely but not for people with disabilities. All up hill even in the cottage the stairs were so steep and with on were to hold on to. My Mother had to...
    Reviewed 26 July 2018
    My stay was with my family and cottage supplied all required, iron, hair dryer etc. Was easy to get to local shops, beach. The only thing there was no notes how to get rid of...
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    About this property
    A well situated three bedroom Portland Stone cottage over three floors with fabulous views over Chesil Beach and The Fleet. Perched on the hill of the island overlooking the Jurassic Coast, you can see why Chesil Beach is part of a World Heritage Site. Just a short walk from Chesil Beach....
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    Isle of Portland, Dorset DT5 1JJ
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Wi-Fi
    • Central Heating
    • Washer
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 Sea View offers the best of modern comforts with period character in a cottage just a short walk from the splendors of Chesil Beach & Cove on the Isle of Portland Dorset. Offering a fabulous kitchen and comfortable accommodation. A character cottage designed to sleep six in three bedrooms in a...
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    Isle of Portland, Dorset DT5 1AA
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Chiswell Cottage1 / 12
    (9)Excellent
    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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    Isle of Portland, Dorset DT5 1AN
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Ocean Views
    • Central Heating
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming three bedroom cottage ticked away a pebble's throw from Chesil Beach. Coral Cove is found between Sea View and Coastguard Cottages at the north end of the island. Ideal as a base for sailing, walking, diving and exploring the island and the rest of the county of Dorset. Vibrant night...
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    Isle of Portland, Dorset DT5 1AD
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Sea Cat Cottage1 / 15
    (2)Average
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Central Heating
    • Wi-Fi
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    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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    Isle of Portland, Dorset DT5 1AH
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    fishermans view1 / 11
    (21)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Ocean Views
    • DVD Player
    • Cable/satellite TV
    • Central Heating
    • Washer
    • Patio
    • Balcony
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 August 2016
    We spent a great week here lovely cottage great sea views, and the weather was amazing easy to get to Weymouth and its sandy beach.
    Reviewed 8 May 2016
    Needed a place to stay where I could relax and recharge my batteries. Fisherman's View was perfect! The cottage is cosy and has everything you could possibly need. When I saw...
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    About this property
    Cottage with sea views over beautiful famous Chesil Beach. South facing patio with sea view. Accommodates up to four . Weekly change over Saturday. Dogs welcome and most places are dog friendly. Nearest beach approximately 200 metres. Minutes from excellent bus service to Weymouth Portland Bill...
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    Isle of Portland, Dorset DT51NJ
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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    Seagull Cottage1 / 20
    (19)Very good
    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 25 August 2018
    Seagull cottage is a great place for a relaxed and comfortable base to explore Portland and Weymouth. The cottage is cosy and fully equipped with all you need as a family, even...
    Reviewed 29 June 2018
    We had a great stay at Portland over 5 nights at Seagull Cottage. Portland is a friendly and beautiful place to stay and walk around, and is so close to places like Weymouth and...
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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 DT5 1JR
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ammonite Cottage is a traditional Portland stone cottage situated on the Isle of Portland, near Weymouth and can sleep four people in two bedrooms.Ammonite Cottage is traditional Portland stone cottage on the Isle of Portland, near to Weymouth in Dorset, benefits from two bedrooms and one bathroom...
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    Castletown, Isle of Portland DT5 1AS
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Parking
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This modern contemporary apartment is in Fortuneswell in Portland in Dorset and can sleep 6 people in 3 bedrooms.Sunset Lodge is a modern contemporary apartment situated in Fortuneswell in Portland in Dorset and benefits from the sea facing balcony. The cottage can sleep 6 people in 2 king size...
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    Castletown, Isle of Portland DT5 1AP
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Grade II listed converted house is in Fortuneswell, Portland in Dorset and can sleep 8 people in 4 bedrooms.The Old Portland Courthouse is a Grade II listed converted house situated in Fortuneswell, Portland in Dorset with antique furnishings and sea views. The house can sleep 8 people in 1...
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    Castletown, Isle of Portland DT5 1AU
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
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    • Wi-Fi
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stylish bungalow on the Isle of Portland near to Weymouth in Dorset and can sleep 4 people in 2 bedrooms.The Palms is a stylish modern bungalow situated on the Isle of Portland near to the town of Weymouth in Dorset and benefits from accommodation all on one floor. The bungalow can sleep 4...
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    Castletown, Isle of Portland DT5 2BZ
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
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    Smoking allowed
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    This contemporary detached house is in Fortuneswell, Portland in Dorset and can sleep 7 people in 4 bedrooms.Osprey House is a contemporary detached house situated in Fortuneswell in Portland in Dorset boasting second floor patio terrace. The house can sleep 7 people in 1 single, 1 twin, 1...
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    Castletown, Isle of Portland DT5 1AU
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Pet friendly
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    Smoking allowed
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    This modern terraced house is in Portand in Dorset and can sleep 5 people in 3 bedrooms.Quarry Trails is a modern terraced house situated in Portland in Dorset and benefits from exceptionally spacious and bright interior. The house can sleep 5 people in 1 king-size double with en-suite shower, 1...
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    Castletown, Isle of Portland DT5 2DQ
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Portland stone semi-detached cottage is in Fortuneswell, Portland in Dorset and can sleep 8 people in 4 bedrooms.Pitt Hayes Cottage is a Portland stone semi-detached cottage situated in Fortuneswell in Portland in Dorset boasting stunning sea views and conservatory. The cottage can sleep 8...
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    Castletown, Isle of Portland DT5 1LQ
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    This traditional Portland cottage is in the village of Fortuneswell, Portland, Dorset and can sleep 5 people in 3 bedrooms.Neptune Cottage is a traditional Portland cottage situated in Fortuneswell, Portland, Dorset and benefits from its location on Chesil Beach. The cottage can sleep 5 people in 1...
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    Castletown, Isle of Portland DT5 1AP
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    This traditional terraced cottage is in the village of Fortuneswell , Portland, Dorset and can sleep 4 people in 2 bedrooms.Langahm Cottage is a traditional terraced cottage situated in Fortuneswell, Portland, Dorset and benefits from beautiful sea views. The cottage can sleep 4 people in 1 Super...
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    Castletown, Isle of Portland DT5 1AB
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
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    This contemporary detached house is in Fortuneswell in Portland in Dorset and can sleep 4 people in 2 bedrooms.St Johns View is a contemporary detached house situated in Fortuneswell in Portland in Dorset with sea views. The house can sleep 4 people in king-size double with en-suite shower and...
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    Castletown, Isle of Portland DT5 1LR
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    This contemporary residential cottage is in the Fortuneswell in Portland in Dorset and can sleep 4 people in 2 bedrooms.Olympic Cottage is a contemporary residential cottage situated in Fortuneswell, Portland in Dorset close to the beach and welcomes 1 dog. The cottage can sleep 4 people in...
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    Castletown, Isle of Portland DT5 1FH
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A Portland stone terraced holiday cottage on the Isle of Portland, Dorset. This cottage sleeps four in two bedrooms. Amenities: Gas central heating. Gas oven and hob, fridge, washing machine, TV with in built DVD, CD, WiFi. telephone for incoming calls. Fuel and power inc. in rent. Bed linen and...
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    Castletown, Isle of Portland DT5 1HR
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This modern 3 storey house is in Fortunewell, Portland, Dorset and can sleep 8 people in 4 bedrooms. Amenities: Sustainable eco-friendly central heating/hot water system, electric oven and hob, microwave, fridge/freezer, washing machine, tumble dryer, dishwasher, TV, Sonos wireless music player,...
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    Castletown, Isle of Portland DT5 1FG
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This terraced house is on the Isle of Portland in Dorset and can sleep 6 people in 3 bedrooms.The View is a terraced house situated on the Isle of Portland near to the town of Weymouth in Dorset and benefits from fantastic scenery along Chesil beach towards Lyme Bay and dramatic West cliffs of the...
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    Castletown, Isle of Portland DT5 1JJ
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    This traditional terraced cottage is in Fortuneswell on the Isle of Portland in Dorset and can sleep 4 people in 2 bedrooms.Unicorn is a traditional terraced cottage situated in Fortuneswell on the Isle of Portland in Dorset and is a short walk from Chesil Beach. The cottage can sleep 4 people in...
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    Castletown, Isle of Portland DT5 1NH
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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