
Vacation rentals in Winchcombe
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Top-rated vacation rentals in Winchcombe
Guests agree: these stays are highly rated for location, cleanliness, and more.

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

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

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.

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!

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

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.

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

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.

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.

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.

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!

'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
Other great vacation rentals in Winchcombe

Book Lovers Retreat Winchcombe

Honey stone and style year round

Grade II listed Cotswold cottage - Abbots Cottage

Dawn Run, Studio Appartment.

Castle Gatehouse, Tower at Sudeley Castle

“The Holiday” Cotswolds Experience

The Room Next Door- Boutique room in the Cotswolds

Anchor Weighbridge House Winchcombe - 2 bedroom
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!
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- Ludlow Castle
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- Manor House Golf Club
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