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Winchcombe Family & Kid Friendly Rentals

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    Travelers to Winchcombe are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    28 Matching Rentals in WinchcombeView all 32 rentals
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    The Cottage, Vineyard Street, Winchcombe, Gloucestershire, GL54 5LP1 / 18
    (77)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Kingfisher, Disabled Friendly, Winchcombe, Cotswolds - Sleeps 10, Winchcombe, Co1 / 34
    (2)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Castle Gatehouse, dog friendly; Sudeley Castle, Cotswolds - Sleeps 4, Dog Friend1 / 30
    (3)Excellent
    2 Bedrooms, 2 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 August 31, 2018
    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 April 9, 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
    This former gatekeeper's house greats you as you enter the majestic Sudeley Castle & Gardens. It's ancient and imposing structure is complemented with symmetrical gardens lined with iron railings and a stone courtyard in the centre. Please note, as per the floor plan, the bedrooms have separate...
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    Winchcombe, Cotswolds GL54 5LP
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 16
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Patio
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    • Housekeeping Included
    • Central Heating
    • Private Yard
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sudeley Castle Country Cottages are the perfect choice for family holidays, reunions and wedding guest accommodation. The cottages are in an Area of Outstand Natural Beauty, surrounded by glorious rolling Cotswold countryside, yet are only a few minutes walk from the historic town of Winchcombe,...
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    Winchcombe, Cotswolds GL54
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sudeley Castle Country Cottages are the perfect choice for family holidays, reunions and wedding guest accommodation. The cottages are in an Area of Outstand Natural Beauty, surrounded by glorious rolling Cotswold countryside, yet are only a few minutes walk from the historic town of Winchcombe,...
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    Winchcombe, Cotswolds GL54
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 7, 2018
    Very nice and clean cottage for up to 3 people, within walking distance of Winchcombe. Easy parking & good facilities.
    Reviewed August 2, 2018
    Beautiful little cottage tastefully decorated with great attention to detail. In an ideal location for exploring the area and within walking distance of all the towns amenities...
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    About this property
    No 61 comfortably sleeps 3, plus an infant, and is situated on a quaint residential road just outside the Cotswold town of Winchcombe. The cottage has two comfy bedrooms and a wood burning stove. There is private parking for one car and a landscaped garden with decking area. No61 is walking...
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    Winchcombe, Cotswolds GL54 5EQ
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Housekeeping Included
    • Grill
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    • Central Heating
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    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 bedrooms, one twin bedroom and two bathrooms. Downstairs, there is a modern fully equipped...
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    Winchcombe, Cotswolds GL54 5JD
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Coates Mill Cottage in the heart of the Cotswolds1 / 13
    (19)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Central Heating
    • DVD Player
    • Washer
    • Grill
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    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 31, 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 September 5, 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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    Location Information
    Winchcombe, Cotswolds GL54 5NH
    Rental Home - 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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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 31, 2018
    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 August 13, 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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sudeley Castle Country Cottages are the perfect choice for family holidays, reunions and wedding guest accommodation. The cottages are in an Area of Outstand Natural Beauty, surrounded by glorious rolling Cotswold countryside, yet are only a few minutes walk from the historic town of Winchcombe,...
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    Winchcombe, Cotswolds GL54 5JA
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sudeley Castle Country Cottages are the perfect choice for family holidays, reunions and wedding guest accommodation. The cottages are in an Area of Outstand Natural Beauty, surrounded by glorious rolling Cotswold countryside, yet are only a few minutes walk from the historic town of Winchcombe,...
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    Winchcombe, Cotswolds GL54 5JA
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    About this property
    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 Cotswolds', Winchcombe. There are walks and...
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    Winchcombe, Cotswolds GL54 5LP
    Rental Home - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Wi-Fi
    • Housekeeping Included
    • Central Heating
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sudeley Castle Country Cottages are the perfect choice for family holidays, reunions and wedding guest accommodation. The cottages are in an Area of Outstand Natural Beauty, surrounded by glorious rolling Cotswold countryside, yet are only a few minutes walk from the historic town of Winchcombe,...
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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
    • Cable/satellite TV
    • Housekeeping Included
    • Washer
    • Central Heating
    • DVD Player
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sudeley Castle Country Cottages are the perfect choice for family holidays, reunions and wedding guest accommodation. The cottages are in an Area of Outstand Natural Beauty, surrounded by glorious rolling Cotswold countryside, yet are only a few minutes walk from the historic town of Winchcombe,...
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    Winchcombe, Cotswolds GL54 5JA
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Anne Boleyn; dog friendly, Sudeley Castle - Sleeps 4, Dog Friendly1 / 9
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 9, 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 and...
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    Winchcombe, Cotswolds GL54 5JA
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Balcony
    • Central Heating
    • Housekeeping Included
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sudeley Castle Country Cottages are the perfect choice for family holidays, reunions and wedding guest accommodation. The cottages are in an Area of Outstand Natural Beauty, surrounded by glorious rolling Cotswold countryside, yet are only a few minutes walk from the historic town of Winchcombe,...
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    Location Information
    Winchcombe, Cotswolds GL54
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sudeley Castle Country Cottages are the perfect choice for family holidays, reunions and wedding guest accommodation. The cottages are in an Area of Outstand Natural Beauty, surrounded by glorious rolling Cotswold countryside, yet are only a few minutes walk from the historic town of Winchcombe,...
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    Location Information
    Winchcombe, Cotswolds GL54 5JA
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Housekeeping Included
    • Wi-Fi
    • DVD Player
    • Central Heating
    • Washer
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sudeley Castle Country Cottages are the perfect choice for family holidays, reunions and wedding guest accommodation. The cottages are in an Area of Outstand Natural Beauty, surrounded by glorious rolling Cotswold countryside, yet are only a few minutes walk from the historic town of Winchcombe,...
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    Winchcombe, Cotswolds GL54
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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 the season). The accommodation...
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    Winchcombe, Cotswolds GL54 5JA
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Central Heating
    • DVD Player
    • Patio
    • Housekeeping Included
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    • Wi-Fi
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sudeley Castle Country Cottages are the perfect choice for family holidays, reunions and wedding guest accommodation. The cottages are in an Area of Outstand Natural Beauty, surrounded by glorious rolling Cotswold countryside, yet are only a few minutes walk from the historic town of Winchcombe,...
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    Winchcombe, Cotswolds GL54
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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
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    Pet friendly
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    Reviewed September 26, 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 September 5, 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
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    13 Bedrooms, 9 Bathrooms, Sleeps 32 Quick View
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    • Balcony
    • Cable/satellite TV
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Set in 90 acres of pasture-land and ancient woodlands with stunning views. The beautiful Cotswold Stone properties: Middle Stanley House, Elmbury and the Craft Studio combine to offer a fabulous location to enjoy the Cotswolds. Enjoy the comforts of a traditional Cotswold stone house during the day...
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    Winchcombe, Cotswolds GL54 5HE
    Rental Home - 13 Bedrooms, 9 Bathrooms, Sleeps 32
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    The Loft1 / 17
    (3)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 8, 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 July 29, 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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Mad Molly's Cottage - MAD MOLLY'S COTTAGE, pet friendly in Winchcombe, Ref 988591 / 26
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Reviewed March 20, 2018
    Really enjoyed our stay at Mad Mollys. It is an expensive cottage but sleeps 4. Right in the heart of Winchcombe all the restaurants pubs and shops are on your door step...
    Reviewed June 18, 2017
    Location was fabulous - 2 minute walk to all amenities.Cottage itself was amazing - every facility that you could dream of and then some. In particular the pot belly fire was...
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    About this property
    Mad Molly's is as unique in name as it is unique inside! Tucked down a little lane and within seconds of some superb restaurants and bars, this cute cottage is the epitome of all things romantic and relaxing. Walking devotees will adore it here, the paths offer some of the best views available in...
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    Location Information
    Winchcombe, Cotswolds GL54 5HY
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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