Some info has been automatically translated. Show original language

Vacation rentals in Winchcombe

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Winchcombe

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

%{current} / %{total}1 / 1
Guest favorite
A charming stone farmhouse is set amidst lush greenery, surrounded by a well-maintained hedge. The building features traditional architectural elements with a welcoming front entrance and outdoor seating area, offering a picturesque view of the serene countryside.
Guest suite in Winchcombe
4.92 out of 5 average rating, 226 reviews

The Annex Self contained suite on a working farm

A self-contained annex on a working farm in the beautiful Cotswold town of Winchcombe. Sitting above the medieval town, the room has spectacular views of the surrounding cotswold hills. Situated 10 minutes walk from the centre of town with lots of pubs, shops and restaurants. Right on the Winchcombe Way and close to the Cotswold Way its ideal for walkers. Secure cycle storage is also available. Broadway, Stow-on-the Wold, Bourton-on-the -Water Cheltenham, Stratford and Oxford are all drivable

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, 168 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
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
4.84 out of 5 average rating, 202 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, 185 reviews

Little Nook Cottage - Dog Friendly & 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
4.93 out of 5 average rating, 123 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

Superhost
A spacious bedroom is furnished with a comfortable king-size bed adorned with a light-colored quilt and decorative pillows. A tray with breakfast items is placed on the bed, and a window allows natural light to fill the room, framed by soft fabric shades.
Cottage in Winchcombe
4.88 out of 5 average rating, 236 reviews

Charming cottage: King Bed, Central, Dogs welcome

The Bolt Hole is a beautiful, refurbished, dog-friendly, Cotswold stone cottage with UK King bed and ensuite bathroom. - Late check-out 11 am + NO cleaning or Airbnb fees - Log burner + New Kitchen w/ dishwasher + Washing Machine - Super Comfortable UK King-Size mattress - Fantastic walks from doorstep - En-suite: 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.

Top guest favorite
A spacious bedroom features a wooden headboard against a neutral wall. Two bedside lamps provide soft lighting beside the bed, which is adorned with decorative pillows. A large window with curtains allows natural light to enter, and neatly arranged towels are displayed on a nearby surface.
Cottage in Winchcombe
4.85 out of 5 average rating, 539 reviews

Apple Tree Cottage, 2 bedroom (double & king beds)

Apple Tree Cottage is a charming Cotswold stone cottage, located right in the heart of Winchcombe with country pubs and shops just a stone's throw from the front door. Located on the most photographed street in the ancient Anglo-Saxon town of Winchcombe. We provide complimentary welcome pack including my homemade plum jam plus our family's delicious Organic Gin+tonic! The cottage living room ceiling is quite low (as is traditional) so taller guests may wish to factor this into their stay

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, 119 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 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
4.93 out of 5 average rating, 135 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—perfect for any season. Set on picturesque Vineyard Street, this lovingly restored former wool cottage blends timeless character with modern comforts. Thoughtfully renovated by your hosts, Paul and Amanda, the boutique two-bedroom home features stylish furnishings and all the contemporary amenities you need for a relaxing stay. Next Availability: 28th October.

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, 148 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.

Guest favorite
A modern kitchen features sleek grey cabinetry and polished white countertops. A stainless steel sink is complemented by a built-in wine fridge. Nearby, large glass doors open to a garden area, allowing natural light to illuminate the space. A decorative welcome sign is placed on the countertop.
Cottage in Winchcombe
4.92 out of 5 average rating, 529 reviews

Cotswold77 - Heart of the Cotswolds

Set in the heart of the Saxon village of Winchcombe a beautifully restored and luxuriously furnished Grade II listed cottage set over three floors with a pretty, sunny garden. Glorious countryside, Cotswold country pubs and a Michelin star restaurant all in walking distance. 6 miles from Cheltenham Racecourse and perfect for the Literature, Jazz and Science Festivals in Cheltenham. An Idyllic spot for exploring the Cotswolds!

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, 138 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 vacation rentals

Frequently Asked Questions

  • Where should I stay in Winchcombe?

    Make yourself at home in Winchcombe by choosing from our most frequently booked neighborhoods. We have over 250 vacation rentals in Winchcombe, over 210 vacation rentals in Greet, and over 350 vacation rentals in Sudeley.

  • Do cottage rentals in Winchcombe have a kitchen?

    Absolutely! We offer over 60 cottage rentals with a kitchen in Winchcombe. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly cottage rentals in Winchcombe?

    Four-legged friends are welcome in Winchcombe. Choose from more than 30 cottage rentals for guests traveling with pets.

  • Do cottage rentals in Winchcombe have wifi?

    Absolutely! We offer over 60 cottage rentals with wifi in Winchcombe. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Winchcombe?

    Experience the best of Winchcombe with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly cottage rentals in Winchcombe?

    Winchcombe has more than 50 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for House Rentals in Winchcombe?

    Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with free parking, over 40 homes with wifi, over 40 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there house rentals with a dedicated workspace in Winchcombe?

    Yes! Work meets play with ease at over 10 house rentals in Winchcombe featuring dedicated workspaces. Stay connected and productive in your home away from home.

Quick stats about vacation rentals in Winchcombe

  • Total vacation rentals

    Explore 130 vacation rentals in Winchcombe

  • Nightly prices starting at

    Winchcombe vacation rentals start at R1,044 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 11,370 verified reviews to help you choose

  • Family-friendly vacation rentals

    90 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 70 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    130 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!

  1. Airbnb
  2. United Kingdom
  3. England
  4. Gloucestershire
  5. Winchcombe