House vacation rentals in Winchcombe

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Quick stats about house rentals in Winchcombe

  • Total vacation rentals

    Explore 50 vacation rentals in Winchcombe

  • Nightly prices starting at

    Winchcombe vacation rentals start at G$20,893 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,200 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Winchcombe vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winchcombe rentals

  • 4.9 Average rating

    Winchcombe stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated house rentals in Winchcombe

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Guest favorite
Home in Boddington
4.94 out of 5 average rating, 189 reviews

Boddington Mill

Boddington Mill is a stunning countryside retreat in the heart of the Cotswolds, steeped in history and rural charm. The building retains industrial mill parts which intersect multiple levels for a unique and generous living space. Its south-facing garden includes outside dining, wood-fired hot tub, and large lawn, home to wildlife and fruit-bearing trees. Inside, the three king sized bedrooms feature luxury bedding beneath vaulted, oak-beamed ceilings and period windows. Sky TV, Sonos speakers.

Top guest favorite
The entrance to the cottage is framed by natural stone walls, showcasing traditional Cotswold architecture. A small overhang provides shelter above the door. Lush greenery and flowering plants enhance the inviting exterior, with a glimpse of the neighboring structure visible to the side.
Home in Stow-on-the-Wold
4.99 out of 5 average rating, 154 reviews

Astley Cottage

Astley is a traditionally styled Cotswold cottage providing you with a home from home experience in Stow on the Wold, one of the most beautiful villages in the Cotswolds We are perfectly located at the end of the town with an array of shops, bars and restaurants to suit every need. Well behaved dogs are welcome. Our fire is for decorative purposes only. Parking suggestions are listed under ‘other details’. Please feel free to message us with any questions you may have! @astleycottagecotswolds

Top guest favorite
The exterior of the cottage is characterized by thatched roofing and Cotswold stone walls. Climbing roses decorate the facade, while a stone pathway leads to a modest seating area. Lush greenery surrounds the building, enhancing the inviting atmosphere of the property.
Home in Chipping Campden
4.95 out of 5 average rating, 382 reviews

Iconic 17th Century Thatched Cottage

Enjoy the beautiful garden in the summer sunshine or hunker down next to the fire in the winter, Hoo Cottage has it all! It is one of the few thatched Cotswold Stone properties, tucked away in the idyllic village of Chipping Campden. We have done our best to bringing out the distinctive character of this historic property, while furnishing it in a luxurious rustic style. The history of the cottage is still up to debate. However, we have found evidence of it playing a role as the village bakery.

Guest favorite
Home in Painswick
4.94 out of 5 average rating, 174 reviews

Breathtaking Cotswolds Restored Chapel Valley View

Step into a rare and remarkable stay at ‘The Old Church’, a lovingly restored & renovated 1820s chapel nestled on the hillside in the idyllic Cotswolds village of Sheepscombe. This enchanting property blends timeless character & period charm with a relaxing contemporary feel. A truly unique picturesque countryside escape. Located in a tranquil woodland setting on the edge of Blackstable Nature Reserve with scenic valley walks, a rustic village setting, a playground & lovely pub down the lane.

Guest favorite
A comfortable living space features a gray sofa paired with a rustic wooden bench. A stone fireplace with a wood-burning stove is framed by an elegant circular mirror, while warm lighting hangs from the ceiling, creating a cozy ambiance. A television stands on a wooden dresser nearby.
Home in Winchcombe
4.93 out of 5 average rating, 163 reviews

Beam House, Winchcombe, sleeps 6 + 2

We don't just offer you somewhere to sleep; at Beam House you can indulge in all the Cotswolds and Cheltenham have to offer knowing you can return to a uniquely styled period house in Winchombe's historic Gloucester Street. Expect soft cotton linens, a wood burning stove, Farrow and Ball paint, exposed beams and stone and oak floors. We offer a unique and stylish retreat ideal for relaxing and exploring. We can host 6 (1 king, 2 double) plus 2 (a sofa bed is available in the drawing room).

Guest favorite
A charming stone cottage is nestled among lush greenery, providing a serene view of the countryside. The expansive lawn is framed by vibrant flowers, while a patio area offers outdoor seating and direct access to the inviting garden space.
Home in Winchcombe
4.95 out of 5 average rating, 102 reviews

Kingfisher Cottage, Disabled Friendly, Cotswolds

Kingfisher Cottage is a delightful, five-bedroom, five-bathroom country residence that's perfect for multi-generational stays, comfortably sleeping 10 guests. This spacious holiday home overlooks open countryside and has a fabulous garden that backs onto the River Isbourne, with plenty of space to dine and relax outside. There's lots of room to entertain all ages, including a large kitchen and breakfast room, a living room, and a superb conservatory with a dining area and a snooker table.

Top guest favorite
A charming stone cottage is framed by blossoming trees and manicured bushes. A gravel pathway leads to the inviting entrance, where natural light streams through the window. Outdoor seating is positioned nearby, providing a serene space to relax.
Home in Kingham
5 out of 5 average rating, 152 reviews

Cotswold cottage in Kingham “The Old Smithy”

Slow down and recharge at The Old Smithy. Built about 600 years ago, this Cotswold stone blacksmiths forge has been transformed into a cosy retreat for two. Kingham is a highly sought after village in the heart of the Cotswolds. With a wealth of brilliant pubs and wonderful countryside walks on our doorstep, you can bring your dog along to enjoy too. The Kingham Plough and The Wild Rabbit, are a short walk away. Daylesford Organic Farm Shop and Bamford club a longer walk/short drive.

Top guest favorite
The image shows a spacious garden featuring well-maintained green grass and fruit trees. A stone-clad house with large glass sliding doors is seen in the background, providing views of the interior. Flower pots are placed by the entrance, adding touches of color to the scene.
Home in Woodmancote
4.93 out of 5 average rating, 121 reviews

Beautiful 4 bed house in Cotswolds

Welcome to our 4 bedroom home located in the village of Woodmancote, near Cleeve Hill & Cheltenham, right next to The Cotswold Hills, Known as the walking capital of England and AONB. Beautifully presented throughout, this self-catering home benefits from an open plan fully equipped kitchen / lounge / diner with sliding patio doors leading out to the garden, separate snug with TV. 4 double bedrooms that can accommodate up to 8 guests, en suite to the Master and a modern family bathroom.

Top guest favorite
A charming stone cottage stands proudly under a clear blue sky, featuring a symmetrical facade with white-framed windows. A neatly landscaped garden with low hedges and shrubs frames the entrance, while a path leads to the front door.
Home in Winchcombe
4.96 out of 5 average rating, 166 reviews

Luxury Cotswolds Cottage with Hot Tub

Escape to our luxurious Cotswolds holiday cottage with a hot tub! Located in the enchanting Cotswold region, our snug-luxe cottage offers the perfect break. With a landscaped garden and proximity to Cheltenham, it's ideal for race enthusiasts and explorers. Experience an unforgettable weekend getaway, family holiday, or celebration with friends in style and comfort. Book now to indulge in the beauty of the Cotswolds and enjoy relaxation, scenic trails, and the charm of Cotswolds living.

Guest favorite
A stone wall surrounds a rustic fireplace, where a log burner emits a warm glow. A polished wooden mantel holds decorative items and five candles. A bottle of champagne rests in an ice bucket beside two glasses, enhancing the cozy ambiance of the sitting room.
Home in Winchcombe
4.88 out of 5 average rating, 130 reviews

Cosy Cotswold Cottage near Cheltenham

Our 200 year old cottage provides the perfect getaway for walkers, cyclists, families or those just wanting some time to unwind and explore the beautiful Cotswold country side. Although the accommodation has been recently refurbished with a new kitchen and bathroom it still retains a wealth of original features including exposed oak beams, stone walls and wood floors. Pubs, cafes, restaurants, shops, Sudely Castle are within walking distance. Cheltenham race course is 6 miles away.

Top guest favorite
A charming row of Cotswold stone cottages is nestled beside a tree-lined pathway. The cottages display traditional slate roofs and white-framed windows, with vibrant flowers and climbing plants adorning their stone walls, creating an inviting residential atmosphere.
Home in Winchcombe
4.93 out of 5 average rating, 120 reviews

4 Vineyard Street

A character filled Cotswold stone cottage including an indoor log burner and a patio with a garden to the rear of the cottage with a coal BBQ which allows for outdoor dining during the summer. Two double bedrooms allow plenty of space for families or friends to holiday in this stylish and welcoming home. This central location means all local amenities are just yards from your front door. See our Cotswold Escapes website and socials for more information and pictures

Top guest favorite
The master bedroom features a king size headboard with a woven design. Two decorative pillows in contrasting patterns rest against the crisp white bedding. Above, framed artwork, including a tiger and a whimsical cat, adorns the wall, complemented by soft bedside lamps.
Home in Winchcombe
5 out of 5 average rating, 167 reviews

'Fifteen off the Green'- 1 Bedroom Cotswolds Home

Nestled on a close next to a peaceful tree-strewn lawn lies ‘Fifteen off the Green’. This fun and unique one bedroom home offers its guests the perfect balance of luxury and design whilst adding all creature comforts to make you feel right at home. Newly refurbished and designed with couples in mind, this home has everything you could need to cook up a storm or just to relax and unwind after a busy day exploring the Cotswolds.

Popular amenities for Winchcombe house rentals

When is the best time to visit Winchcombe?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$52,233 GYDG$48,472 GYDG$47,845 GYDG$54,113 GYDG$46,592 GYDG$41,786 GYDG$48,054 GYDG$54,322 GYDG$44,084 GYDG$49,517 GYDG$49,517 GYDG$62,470 GYD
Avg. temp5°C5°C7°C9°C12°C15°C18°C17°C15°C11°C7°C5°C
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