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Cottage vacation rentals in Winchcombe

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Top-rated cottage rentals in Winchcombe

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Top guest favorite
A wide view of rolling green hills displays a tranquil landscape. A small pond is nestled among lush foliage, surrounded by paths cutting through the greenery. Trees are scattered throughout the scene, contributing to the natural beauty of the area.
Cottage in Cheltenham
4.92 out of 5 average rating, 518 reviews

The Bothy cottage in the Cotswolds

The Bothy is a conversion of a 17th Century Cotswold stone stable and a 20th Century kennel building. On the ground floor is the living room with a beautiful wood burning stove, a fully equipped kitchen, a comfortable double bedroom and a modern shower room. Whilst upstairs, which is accessed from a narrow oak staircase, you can find the twin bedroom. The living room has been fitted to retain all its original features and is furnished in period style. I have included many Georgian and Victorian pieces and have also included a large settee and two arm chairs, dining table and chairs for 4, corner cupboard and a dash of the 21st Century with a Sky television. The Bothy is beautifully situated in the Postlip Coombe on the leeward side of the Cotswolds highest hill and yet only minutes from Winchcombe, a classic Cotswold "wool" town, renowned for its excellent shops, restaurants and architecture.

Guest favorite
A cozy living area is highlighted by a stone fireplace featuring a log burner. Two comfortable armchairs are positioned near a coffee table, adorned with decorative items. Soft lighting is provided by a lamp, enhancing the warm atmosphere of the space.
Cottage in Winchcombe
4.92 out of 5 average rating, 179 reviews

Thimble Cottage. Winchcombe

Charming 200 year old Cotswold stone Cottage with oak beams and log burner. Situated in the heart of the ancient Saxon town of Winchcombe. Two lovely bedrooms, one with king size bed and the second with two single beds. Fully furnished to a high standard with an attractive long garden and patio seating area. Close to all amenities, pubs, restaurants and local produce shops i.e bakers, butchers and delicatessen. Sudeley Castle and grounds are a short walk from the cottage. Pet friendly No smoking

Guest favorite
Cottage in Winchcombe
4.88 out of 5 average rating, 242 reviews

Luxury Dog friendly cottage, King Bed, log fire

The Bolt Hole - a charming, refurbished, dog-friendly, Cotswold stone cottage with UK King bed, central to pubs and cafes - Late check-out 11 am + NO cleaning or Airbnb fees - Log burner + New Kitchen w/ dishwasher + Washing Machine - V Comfortable UK King-Size mattress - Fantastic walks from doorstep - En-suite: new large shower 🚿+ roll-top bath 🛀 - Smart TV - Cot and highchair Nestled in the heart of stunning Winchcombe; steps from pubs, restaurants, cafes, and historic Sudeley Castle.

Guest favorite
A spacious bed is dressed in white linens, complemented by textured yellow cushions and a woven throw. A bedside lamp and a wooden nightstand are visible, along with a framed piece of artwork depicting a woman in profile.
Cottage in Winchcombe
4.85 out of 5 average rating, 213 reviews

Penny Cottage - Cozy Cotswold cottage

Penny Cottage is in the heart of the former Saxon town of Winchcombe. It is a traditional Cotswold cottage with a working inglenook fireplace. It is on the Cotswold Way and has access to miles of country walks. Sudeley Castle, the resting place of the only Queen of England to be buried outside a royal palace, is within walking distance. A variety of pubs and restaurants can all be found within a 5 minute walk. The town also boasts a variety of independent shops, and two small supermarkets.

Top guest favorite
The living area features a cozy seating arrangement with a neutral-toned sofa and decorative cushions. A natural woven pendant light hangs above, illuminating the space. A rustic coffee table sits on textured flooring, accompanied by warm tones and a charming wreath adorning the entrance.
Cottage in Winchcombe
4.98 out of 5 average rating, 217 reviews

Little Nook Cottage - Cosy & Large Garden

Located in the heart of Winchcombe with far reaching views over the rolling Cotswold hills, Little Nook Cottage is a charming bolt hole, perfect for couples or a small family from which to explore the Cotswolds. You will find beautifully crafted beams and original stone floors paired with all the luxuries you need for a relaxing break. Featuring a cosy living/dining room with wood burning fire, a super comfy double room and even a dedicated work space should you wish to work away from home!

Guest favorite
The charming exterior of a stone cottage is depicted, showcasing a green door under a decorative canopy. Flanking the entrance are small potted plants. A friendly dog is seated on the doorstep, adding a welcoming touch to the quaint facade.
Cottage in Winchcombe
4.9 out of 5 average rating, 136 reviews

Cosy Cotswold Cottage in the centre of Winchcombe

Vineyard street is an unrivaled position in Winchcombe, a unique town in all it has to offer, where visitors are welcomed and quickly feel like locals and get to enjoy a real part of Cotswolds Life. No. 5 is a traditional cosy cottage, decorated and furnished to a high standard to ensure our guests comfort and needs. We are local owners and are on hand with any questions and to offer recommendations to make the most of your visit. Secure garden, dogs are very welcome, also allowed in pubs

Top guest favorite
A stone cottage is adorned with vibrant wisteria, cascading purple flowers creating a natural display against the exterior. Green shutters complement the floral arrangement, while the surrounding lawn is well-maintained, enhancing the cottage's charming setting in the countryside.
Cottage in Stanley Pontlarge
4.98 out of 5 average rating, 290 reviews

Stunning Cotswold cottage, log burner, Winchcombe

Gorgeous romantic luxury Cotswold cottage with direct access to walks. Up to 2 well behaved small/medium dogs are welcome or enquire (see dog rules). The Old Mill House is 2 miles to Winchcombe, 5 miles Cheltenham Racecourse, 9 miles central Cheltenham. Living room with logburner, bedroom with kingsize bed, kitchen - microwave, dishwasher, induction hob, oven Nespresso machine, Smeg fridge/freezer. Shower room. Neal's Yard toiletries. Fast broadband. EV charging. Muddy paw pet washer.

Guest favorite
A lush garden is depicted, featuring vibrant green foliage and blooming flowers. Wisteria hangs gracefully from above, complementing the scenic view of the rolling countryside in the background. A seating area with wooden furniture is visible, inviting relaxation amidst the natural surroundings.
Cottage in Winchcombe
4.84 out of 5 average rating, 155 reviews

Idyllic cottage with direct Access to Cotswold Way

17th-century gem: original features, tranquil stream inside the property, and a private picturesque garden with DIRECT ACCESS to the Cotswold Way! Stay in a 300 years old cottage. Nestled in an AONB, this Grade II listed hideaway offers a peaceful, idyllic stay within a 15-minute drive from Cheltenham. Great to cosy up on wet days, explore the area, or enjoy our garden on a sunny day. Perfect for romantic getaways, nature lovers or people who want to escape the humdrum of everyday life.

Top guest favorite
A charming stone cottage stands with a well-maintained exterior, featuring a gravel drive and neatly trimmed bushes on either side. A large glass door welcomes visitors, while the sloped roof and traditional chimney add character to the design.
Cottage in Moreton-in-Marsh
4.94 out of 5 average rating, 104 reviews

Luxury Cottage, WOW en~suite and private parking.

“ The couples cottage “ a romantic Cotswolds cottage, this beautiful cottage has the real WOW factor. A spacious one bedroom cottage with and a stunning decadent en_suite, resplendent with two side by side slipper baths positioned opposite a bespoke wall mural of Florence. Tucked away down a quiet side street off Moreton in Marsh main high street you have the best of both worlds. All the charm of a country cottage but with all amenities close by and stunning countryside all around.

Top guest favorite
A charming stone cottage is framed by lush greenery and colorful flowering plants. A wooden gate leads to a gravel driveway, while rolling hills can be seen in the background under a clear blue sky.
Cottage in Broadway
5 out of 5 average rating, 133 reviews

Hobleys Cottage Stanton Nr Broadway

Hobleys Cottage is positioned on the edge of the historic village of Stanton which is widely regarded as one of the most picturesque in the Cotswolds. Recently refurbished the luxury accommodation is light and spacious with a well-equipped kitchen, open plan dining and sitting room. Wake up to stunning views over the adjoining pasture fields; a relaxing setting and a perfect base from which to explore the Cotswalds. The village pub The Mount Inn is within walking distance.

Top guest favorite
A charming row of 18th-century cottages is depicted, featuring stone exteriors with traditional slate roofs. Lush vegetation and climbing plants adorn the walls, while windows invite natural light. The pathway, bordered by vibrant flowers, leads to an inviting garden space that enhances the cottage's appeal.
Cottage in Winchcombe
4.94 out of 5 average rating, 143 reviews

The Feathered Nest an idyllic Cotswolds escape.

Nestled in the heart of historic Winchcombe, The Feathered Nest offers a welcoming escape in the beautiful North Cotswolds. Set on picturesque Vineyard Street, this lovingly restored former wool cottage blends timeless character with modern comforts. Thoughtfully renovated by the owners this the boutique two-bedroom home features stylish furnishings and all the contemporary amenities you need for a relaxing stay. Available for mid week or long weekend breaks this February.

Superhost
A charming stone cottage showcases a historic brewery sign on its facade, framed by flowering plants in window boxes. The blue door provides a vibrant contrast against the earthy tones of the building, while traditional windows allow natural light to fill the interior.
Cottage in Winchcombe
4.83 out of 5 average rating, 156 reviews

Barley Cottage

A character filled centrally-located cottage sure to enable a relaxing stay in our picturesque Cotswold town. An indoor log burner keeps the place cosy, and a small patio with garden to the rear of the cottage allows for outdoor dining during the summer. Cook for yourselves in the fully equipped kitchen or eat out at the many eateries in town right on the doorstep. A fully refurbished bathroom with walk in shower and sofa bed that can sleep 2 are also at your leisure.

Popular amenities for Winchcombe cottage rentals

When is the best time to visit Winchcombe?

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Avg. priceﺩ.ﺇ507ﺩ.ﺇ529ﺩ.ﺇ705ﺩ.ﺇ676ﺩ.ﺇ687ﺩ.ﺇ720ﺩ.ﺇ709ﺩ.ﺇ723ﺩ.ﺇ646ﺩ.ﺇ650ﺩ.ﺇ613ﺩ.ﺇ760
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Quick stats about cottage rentals in Winchcombe

  • Total vacation rentals

    Explore 60 vacation rentals in Winchcombe

  • Nightly prices starting at

    Winchcombe vacation rentals start at ﺩ.ﺇ294 per night before taxes and fees

  • Verified guest reviews

    Over 6,860 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Winchcombe vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winchcombe rentals

  • 4.8 Average rating

    Winchcombe stays are highly rated by guests—averaging 4.8 out of 5!

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