
Pet-friendly holiday rentals in Winchcombe
Find and book unique pet-friendly homes on Airbnb
Quick stats about holiday rentals that are pet-friendly in Winchcombe

Total holiday rentals
Explore 70 holiday rentals in Winchcombe

Nightly prices starting at
Winchcombe holiday rentals start at $115 SGD per night before taxes and fees

Verified guest reviews
Over 5,770 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
70 of Winchcombe holiday rentals include wifi 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!
Top-rated pet-friendly home rentals in Winchcombe
Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

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
PetsWalkabilityCheckout

Penny Cottage - Cosy 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.
Outdoor spacesWalkabilityValue

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!
Outdoor spacesWalkabilityHospitality

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).
Outdoor spacesWalkabilityView

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
Outdoor spacesPetsQuiet

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. Faith in Nature toiletries. Fast broadband. EV charging. Muddy paw pet washer.
WalkabilityPetsAccess

The Beehive
A dog friendly shepherds hut in the Cotswolds, ideal for those seeking a tranquil retreat. It features a comfy double bed, wood stove with enough logs to get started, bathroom and kitchen area. Enjoy the garden with a patio set, perfect for relaxing. Located near Gretton, it provides access to the Cotswolds' beauty, historic towns, and National Trust sites. Nearby, explore trails, Sudeley Castle, and racecourses. Experience a blend of rustic allure and contemporary amenities at 'The Beehive’
Outdoor spacesWalkabilityBreakfast

Luxury Central, Dog friendly, King Bed, Log fire
The Bolt Hole is a charming, refurbished, dog-friendly, Cotswold stone cottage, central to pubs and cafes - Late check-out 11 am + NO cleaning or Airbnb fees - Easy FREE on-street parking - Log burner + dishwasher + Washing Machine - V Comfortable UK King 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.
Outdoor spacesWalkabilityCondition

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.
WalkabilityPetsHot tub

Luxury Shepherds Hut with Private Bath Hut
Located within it's own private field, neighbouring The Royal Oak pub (Gretton), this is the premium hut of three with outstanding Cotswolds views for an unforgettable escape. The hut's industrial style oozes elegance. A comfy king-size bed and stylish shower room shoulder up the middle living space which boasts a log burner, kitchenette and dining area. Guests also have access to their own private separate bath hut. An ideal spot to switch off and relax. Home is where the hut is!
WalkabilityOutdoor spacesAmenities

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
WalkabilityPetsCleanliness

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 a few items when you arrive including my homemade jam! The cottage living room ceiling is quite low (as is traditional) so taller guests may wish to factor this into their stay
PetsOutdoor spacesAccuracy
Popular amenities for Winchcombe pet-friendly home rentals
Pet-friendly house rentals

Beautiful 4 bed house in Cotswolds
PetsWalkabilityHospitality

Beautiful 1-bedroom home in Broadway
WalkabilityOutdoor spacesAccuracy

Almsbury Farmhouse at Sudeley Castle, Cotswolds
WalkabilityOutdoor spacesBathroom

Riverside Cottage • Opposite Arlington Row • Pets
WalkabilityPetsHospitality

Astley Cottage
WalkabilityOutdoor spacesAmenities

Boddington Mill
Outdoor spacesWalkabilityEV charging

Stunning 17th century 3 bedroom cottage
PetsWalkabilityCleanliness

Attractive Period House with breath-taking views
WalkabilityOutdoor spacesNearby
Pet-friendly home rentals with a pool

Dovecote Cottage
WalkabilityPetsIndoor spaces

Cotswolds Cottage, Heated Pool, Tithe Barn Views
PetsOutdoor spacesCheckout

Stylish Cotswolds Retreat w/ Heated Pool, Sleeps 8
Outdoor spacesPetsIndoor spaces

Hyde Mill Cottage
WalkabilityOutdoor spacesAmenities

Charming Stone Cotswold Cottage with Pool Access
Outdoor spacesWalkabilityValue

Boundary Court Barn, Selsley common, Stroud
PetsOutdoor spacesParks

Rural idyll, with tennis court and swimming pool
PetsWalkabilityHiking

Modern contemporary home in beautiful setting
Outdoor spacesWalkabilityKitchen
Private, pet-friendly home rentals

Stanton Cotswolds The Hay loft 2 Bed, Cottage
Outdoor spacesPetsAccess

Luxury 1 bed, Broadway, Cotswolds. Private parking
Outdoor spacesWalkabilityLocation

Luxury Cotswold Lodge |Stunning View of Cheltenham
Outdoor spacesPetsKitchen

Pretty Chocolate Box Thatched Cottage
WalkabilityOutdoor spacesLocation

Secluded cottage in the heart of Stow on the Wold
WalkabilityPetsParking

Lavender Lodge - Bourton on the Water
Outdoor spacesPetsValue

Luxury 16th C. Cottage Broadway
Outdoor spacesWalkabilityCheckout

Stylish Cotswold Retreat with Dog Friendly Garden
PetsWalkabilityCleanliness
When is the best time to visit Winchcombe?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $248 SGD | $224 SGD | $293 SGD | $269 SGD | $294 SGD | $292 SGD | $262 SGD | $303 SGD | $237 SGD | $243 SGD | $283 SGD | $305 SGD |
| Avg. temp | 5°C | 5°C | 7°C | 9°C | 12°C | 15°C | 18°C | 17°C | 15°C | 11°C | 7°C | 5°C |
Destinations to explore
- Silverstone Circuit
- Cotswolds AONB
- University of Oxford
- National Exhibition Centre
- Blenheim Palace
- Wye Valley Area of Outstanding Natural Beauty (AONB)
- Lower Mill Estate
- Cheltenham Racecourse
- West Midland Safari Park
- University of Warwick
- Utilita Arena Birmingham
- Cadbury World
- Ludlow Castle
- Coventry Building Society Arena
- Cotswold Wildlife Park
- Bath Abbey
- University of Birmingham
- Puzzlewood
- Bicester Village
- Sudeley Castle
- Warwick Castle
- Alexander Stadium
- No. 1 Royal Crescent
- Waddesdon Manor





