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Holiday Homes in Winchcombe

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    Travellers to Winchcombe are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    All 29 Rentals in Winchcombe
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    The Cottage, Vineyard Street, Winchcombe, Gloucestershire, GL54 5LP1 / 36
    (74)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Kingfisher Cottage, Disabled Friendly, Sleeps 10, Walks on Doorstep, Parking1 / 25
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    No61 Cosy Cotswold Cottage in Winchcombe1 / 13
    (9)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    Castle Gatehouse, Sleeps 4, Dog Friendly1 / 37
    (3)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Wi-Fi
    • Central Heating
    • Cable/satellite TV
    • DVD Player
    • Balcony
    • Washer
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    What can I say, The Castle Gatehouse is simply Amazing !! such a beautifully kept, clean resisdance, we absolutely loved it, in fact my wife kept asking could we buy it !!Very...
    Reviewed 9 April 2018
    Castle Gatehouse is a lovely, quirky and charming place to spend a few days. Spotlessly clean spacious bedrooms and kitchen. The enclosed garden was perfect for our dog. It...
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    About this property
    The Gatehouse to Sudeley Castle is now available as a holiday home! Situated on the edge of the Sudeley Estate, the gatehouse structure consisting of two large towers that support the gate are considered the strongest defensive positions in the castle. Within walking distance of the village known...
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    Winchcombe, Cotswolds GL54 5LP
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Cotswold holiday lodge with views1 / 15
    (86)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Private Garden
    • Mountain Views
    • Wi-Fi
    • Secure Parking
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Really enjoyed our short stay here. Great holiday lodge that is very well equipped with everything you would need. Lovely little welcome pack and a nice touch with the bathrobes...
    Reviewed 9 July 2018
    A perfect place to unwind from the rush of everyday life. We picked a perfect week off with the hot weather only adding to the stay.The cottage is situated next to the owner...
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    About this property
    Situated in the unspoilt village of Brockhampton in the heart of the Cotswolds Area of Outstanding Natural Beauty yet close to Regency Cheltenham, Coomb Cottage is a luxury log cabin with wide-ranging views out across our magnificent limestone uplands. Coomb Cottage has been renovated to the...
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    Winchcombe, Cotswolds GL54 5XJ
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Almsbury Farmhouse, Sleeps 14, Dog Friendly, Walks & Cycling on your Doorstep1 / 73
    (4)Excellent
    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Patio
    • Central Heating
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    • Grill
    • Cable/satellite TV
    • Housekeeping Included
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 May 2018
    What a fantastic house and stay we had at Almsbury Farmhouse. The house is great and very suitable for a bigger group of people. The location is amazing as well, Winchcombe is...
    Reviewed 22 April 2018
    Booked this house for my 40th birthday. The location is amazing - a couple of minutes walk into Winchcombe and almost next door to the entrance of Sudeley castle. The house is...
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    About this property
    Visit England 4* Gold award-winning farmhouse; unpretentious and very welcoming, there is a great sense of style about this recently refurbished 18th century farmhouse. Situated on the edge of the Sudeley Estate, the farmhouse is within walking distance of the village known as the 'The Jewel of the...
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    Winchcombe, Cotswolds GL54 5LP
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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    4 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    • Patio
    • Grill
    • Wi-Fi
    • Central Heating
    • Housekeeping Included
    • DVD Player
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A Visit England 4* Gold award-winning property, located in the heart of idyllic Winchcombe, this beautifully renovated 18th century cottage, sleeps up to seven guests, in four bedrooms one of which is a private annex. Thanks to its many skylights and windows, light sweeps through the cottage to...
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    Winchcombe, Cotswolds GL54 5LP
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 7
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    Coates Mill Cottage in the heart of the Cotswolds1 / 26
    (19)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Central Heating
    • DVD Player
    • Washer
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 December 2017
    Close to the town - and in better weather - easy walking distance to local pubs, restaurants and shops. Good range of place to eat though a little on the pricey side.The...
    Reviewed 5 September 2017
    Stayed for a short weekend but wish it was longer. We found the cottage situated along a row of cottages by a stream. The cottage was beautifully decorated and had everything...
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    About this property
    Coates Mill Cottage is a 200-year-old Cotswold stone property with large private garden. It lies in a quiet position at the end of a terrace, in a wooded hollow with a mill stream opposite . The property's rural setting belies the fact that it is only a 10-minute walk from the centre of Winchcombe...
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    Winchcombe, Cotswolds GL54 5NH
    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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    • Parking
    • Housekeeping Included
    • Wi-Fi
    • DVD Player
    • Central Heating
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A delightful cottage on the Sudeley Castle Estate in the heart of historic Winchcombe, perfect for groups who can’t get enough of the great outdoors. The Living Space Princess Elizabeth cottage was originally a paper mill that has been restored to make accommodation with exposed walls and...
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    Winchcombe, Cotswolds GL54
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The Loft1 / 17
    (3)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • DVD Player
    • Wi-Fi
    • Housekeeping Included
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 April 2018
    The high street location was great, ideally placed to visit the shops or nip out for forgotten provisions. The apartment was lovely, with surprisingly spacious living space that...
    Reviewed 30 July 2016
    I was lucky enough to stay at The Loft in June this year. It is a lovely apartment in a fantastic position set above a dress shop in The centre of town. The Loft is perfectly...
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    About this property
    The apartment is in the centre of the delightful Cotswold town of Winchcombe. It is housed in an old Cotswold stone building on the first and second floors. The ground floor houses a chic ladies' shop. It is open plan with plenty of windows so is spacious, light and airy and gets the full of...
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    Winchcombe, Cotswolds GL54 5LH
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Misty View Cotswold Cottage1 / 5
    (7)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Central Heating
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 September 2017
    Misty View is such a lovely cottage; very convenient to shops and restaurants in Winchcombe. The accommodation is very clean and comfortable, with ensuites for both bedrooms...
    Reviewed 5 September 2017
    The title of my review says it all. Misty View is small, but it is comfortable, well equipped, and well located. It is just two minutes from the heart of a wonderful small...
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    About this property
    This modern Cotswold stone cottage lies close to the heart of the delightful town of Winchcombe. Adjoining another property, it is set along a quiet lane, 2 minutes' walk from an excellent range of shops, historic pubs, restaurants and beautiful Sudeley Castle (once home of a Queen and venue of Liz...
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    Winchcombe, Cotswolds GL54
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Pinnock Wood Farm Shepherds Hut1 / 17
    (30)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
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    • DVD Player
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Easy to find following the directions, met by host who showed us the basics and then left us be. Fantastic accommodation, every thing you need for a superb break. Shower and...
    Reviewed 9 August 2018
    We've just spent a delightful two nights at this superb luxury Shepherds Hut whilst enjoying a casual meander through the Cotswolds visiting Bourton on the Water, Stow on the...
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    About this property
    Pinnock Wood Farm Shepherds Hut is located in a quiet rural setting on a working livestock farm in the North Cotswolds. Situated close to the historic town of Winchcombe. The Shepherds Hut is fully serviced with a Double bed, fully fitted kitchen, bathroom with heating throughout,...
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    Winchcombe, Cotswolds GL54 5AX
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Housekeeping Included
    • Grill
    • Wi-Fi
    • DVD Player
    • Central Heating
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The private guest cottage of the owners Sudeley Castle, is now available for rent. The Guest Cottage has been completely renovated to the highest standard and contains many items of furniture and pictures from the Castle's private collection. Upstairs, the accommodation comprises two double...
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    Winchcombe, Cotswolds GL54 5JD
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Anne Boleyn, Sudeley Castle, Winchcombe, Cotswolds1 / 12
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 July 2018
    what a great place to stay ideal base for walking and exploring the Cotswold. There are several shops/ pubs/ take aways for your self catering needs. Many walks in several...
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    About this property
    This is a semi-detached cottage, named in memory of Anne Boleyn, who spent a week at Sudeley Castle & Gardens in 1535 with the new king, Henry VIII. Guests staying at Anne Boleyn cottage enjoy complimentary entrance to Sudeley Castle & Gardens (during the season). The cottage sleeps four people...
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    Winchcombe, Cotswolds GL54 5JA
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    *COTTAGE CENTRAL WINCHCOMBE, 2 mins walk to centre, sleeps 6 from L100 per night1 / 10
    (20)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    • Balcony
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    • Terrace
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Lovely cottage, a street behind the main street, shops close by and cafe's. Excellent place to unwind. Stayed there comfortably with a family of four adults and one toddler. The...
    Reviewed 13 August 2018
    Brilliant cottage. For the price you r paying this is a bargain. 2 minute walk from the high street. Winchcombe is lovely. 5 stars. Would definitely stay again.
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    About this property
    Our comfortable cosy Cotswold cottage on the ground floor has a fitted kitchen which includes a dishwasher, cooker, hob, microwave and fridge.A Washer is situated in the under stairs cupboard.The kitchen leads to a dining room with a large pine table and six comfortable upholstered chairs.Beyond...
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    Winchcombe, Cotswolds GL545PX
    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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    • DVD Player
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A delightful cottage on the Sudeley Castle Estate in the heart of historic Winchcombe, perfect for groups who can’t get enough of the great outdoors. The Living Space Oliver Cromwell is an apartment that was restored from a paper mill to make spectacular accommodation with exposed stone walls and...
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    Winchcombe, Cotswolds GL54
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Emma Dent is a large detached cottage 2-bedroom cottage on two floors, which sleeps four people in two bedrooms or six using a double sofa bed downstairs and can additionally accommodate a cot; both bathrooms are upstairs. There is a real sense of history about the cottage, which is named after the...
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    Winchcombe, Cotswolds GL54 5JA
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lord High Admiral is the latest addition to our country cottage complex. Lord High Admiral is one of the official titles conveyed upon Sir Thomas Seymour by King Edward VI. Guests staying at the cottage enjoy complimentary entrance to Sudeley Castle & Gardens (during March to October). The...
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    Winchcombe, Cotswolds GL54 5JA
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Central Heating
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A delightful cottage on the Sudeley Castle Estate in the heart of historic Winchcombe, perfect for groups who can’t get enough of the great outdoors. The Living Space Sleeps 4 + 2; Wheelchair access Queens cottage has been converted from the old engine house to form a unique detached cottage,...
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    Winchcombe, Cotswolds GL54
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    St. Kenelm is an apartment that was restored from a paper mill to make spectacular accommodation with exposed stone walls and original beams. It is named after St Kenelm, who was a member of the royal family of Mercia, a boy king and martyr, who was murdered by an ambitious relative and his body...
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    Winchcombe, Cotswolds GL54 5JA
    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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    • Central Heating
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A delightful cottage on the Sudeley Castle Estate in the heart of historic Winchcombe, perfect for groups who can’t get enough of the great outdoors. The Living Space This is a semi-detached cottage, named after Queen Mary, who in 1944 visited the Dent-Brocklehurst family at Sudeley Castle,...
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    Winchcombe, Cotswolds GL54
    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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    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This apartment cottage, which sleeps 4 people, is converted from the old forge. It is named in memory of George III, who came to visit Sudeley Castle & Gardens on a number of occasions in the late 18thcentury. Guests staying at George III enjoy complimentary entrance to Sudeley Castle & Gardens...
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    Winchcombe, Cotswolds GL54
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    About this property
    This apartment, which sleeps 3 people, is converted from the old forge. It is named in memory of Charles I, who took refuge at Sudeley Castle after his failed siege of Gloucester during the English Civil War. Guests staying at Charles I enjoy complimentary entrance to Sudeley Castle & Gardens...
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    Winchcombe, Cotswolds GL54 5JA
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Pet friendly
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    About this property
    Milestone, aka the Big Cotswold Cottage, is an affordable, large, luxury home in a beautiful location. Perfect for friend and family reunions, hen parties and corporate team gatherings. Note: If you are booking for 7 days, please get in touch for a custom quote as we offer a weekly discount....
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    Winchcombe, Cotswolds GL54
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 16
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    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    About this property
    This apartment, which sleeps 3 people, is converted from the old forge and was completely renovated in November 2017. It is named in memory of Prince Rupert, who was a nephew of Charles I and commanded the Royalist cavalry during the English Civil War, made Sudeley his headquarters. Guests...
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    Winchcombe, Cotswolds GL54 5JA
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A delightful cottage on the Sudeley Castle Estate in the heart of historic Winchcombe, perfect for groups who can’t get enough of the great outdoors. The Living Space Lady Jane Grey is one of our largest properties, named after Lady Jane Grey, who lived at Sudeley Castle before her brief nine-day...
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    Winchcombe, Cotswolds GL54
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Anvil Cottage1 / 10
    (50)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Reviewed 3 weeks ago
    Lovely cosy cottage, perfectly equipped for a weekend break for two. Beautifully furnished and very comfortable. Julia has thought of everything you could need and also included...
    Reviewed 16 August 2018
    We stayed here for three nights for our anniversary and found it to be a great base - as we were only there a short time we just left the car where it was and walked to the...
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    About this property
    Anvil Cottage is a lovely one bedroom self-catering holiday cottage located in the heart of Winchcombe. This quirky holiday cottage makes a great base for a short break or longer holiday whilst exploring the Cotswolds. The cottage is well equipped - we hope to offer everything that you will need...
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    Winchcombe, Cotswolds GL54 5PY
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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
    Welcome to Millers Cottage, brought to you exclusively by Character Cottages, local specialists in stylish, Cotswold holiday rentals Millers Cottage is one of a row of traditional Cotswold stone cottages in the heart of Winchcombe, an ancient Saxon town situated on the famous Cotswold Way....
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    Winchcombe, Cotswolds GL54 5HU
    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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    About this property
    This characterful stone cottage is situated in the English town of Winchcombe and can sleep six people in three bedrooms. Region: Visitors to the Cotswolds have long treasured memories of charming towns and villages built from the famous honey-coloured stone, it now boasts a thriving community of...
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    Winchcombe, Cotswolds GL54 5PS
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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