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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.

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Cottage in Cheltenham

4.91 out of 5 average rating, 448 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 suite in Winchcombe

4.91 out of 5 average rating, 164 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

Cottage in Winchcombe

4.94 out of 5 average rating, 101 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

Cottage in Winchcombe

4.83 out of 5 average rating, 183 reviews

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.

Cottage in Winchcombe

4.93 out of 5 average rating, 114 reviews

The Feathered Nest an idyllic Cotswolds escape.

The Feathered Nest is a delightful Cotswolds escape at any time of year. Vineyard Street is a picture postcard street in the heart of the Anglo-Saxon town of Winchcombe in the North Cotswolds. Paul and Amanda have lovingly restored this former wool cottage into a boutique two bedroom cottage with all the modern fixtures and fittings required by our discerning guests. The property has a stunning private courtyard garden which is a perfect retreat to listen to the bells of St Peter's at sundown.

Shepherd’s hut in Winchcombe

4.97 out of 5 average rating, 159 reviews

Stunning Cotswold Views, Idyllic, Ensuite TV/WiFi

Cosy Scandinavian styled, ensuite, bespoke Shepherd's Hut set in a stunning valley with extensive views. Area of Outstanding Natural Beauty, The Cotswolds. Spectacular local & National Walking Trails. Picturesque 1 mile walk to medieval Winchcombe. *Visit Sudeley Castle, once home to King Henry VIII & resting place of his Queen, Katherine Parr, set in award winning gardens & grounds. Festivals and events all year round. Discover our great history, fine restaurants, superb cafés & cosy pubs.

Cottage in Winchcombe

4.85 out of 5 average rating, 485 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

Guesthouse in Winchcombe

4.96 out of 5 average rating, 320 reviews

Charming ‘mini cottage’ bedroom and shower room

A pretty and private little Cotswold stone bakehouse converted to a bedroom and shower room with beautiful Cotswold views set in rolling farmland on edge of historic hamlet of Hailes. We are right on the Cotswold Way and an ideal stop off after the first leg or walk the myriad of footpaths around us straight from the door. Within easy access of Cheltenham racecourse and the lovely villages of the Cotswolds, the many country pubs or a visit to the amazing Giffords Circus.

Cottage in Winchcombe

4.83 out of 5 average rating, 118 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.

Cottage in Winchcombe

4.91 out of 5 average rating, 473 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!

Home in Winchcombe

5 out of 5 average rating, 106 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.

Cottage in Winchcombe

4.97 out of 5 average rating, 236 reviews

No61 - Cosy Cotswold Cottage in Winchcombe

No61 sleeps 3 adults plus an infant in a cot and is situated on a quaint residential road just outside the Cotswold town of Winchcombe. The cottage has private parking, two comfy bedrooms and a wood burning stove for the winter. The flower filled garden has a suntrap decking area for the summer with table and chairs. No61 is a 5 minute walk from a selection of restaurants, pubs and coffee shops.

Vacation rentals for every style

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Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Hotels

Stylish accommodations and amenities

Popular amenities for Winchcombe vacation rentals

Free parking on premises

Air conditioning

Stay near Winchcombe's top sights

Sudeley Castle248 locals recommend

The Royal Oak76 locals recommend

Gloucestershire Warwickshire Steam Railway45 locals recommend

The Lion Inn41 locals recommend

Hailes Abbey40 locals recommend

Belas Knap Long Barrow37 locals recommend

Other great vacation rentals in Winchcombe

Cottage in Winchcombe

4.94 out of 5 average rating, 34 reviews

Comfortable Grade 2 listed cottage with parking

Home in Winchcombe

4.92 out of 5 average rating, 90 reviews

Beam House, Winchcombe, sleeps 6 + 2

Home in Winchcombe

4.89 out of 5 average rating, 96 reviews

Boutique cottage in the heart of Winchcombe

Cottage in Winchcombe

4.96 out of 5 average rating, 24 reviews

Cosy 2 Bedroom Cotswold Cottage with Large Garden

Cottage in Winchcombe

4.86 out of 5 average rating, 14 reviews

Cosy Cotswold Cottage; Woodburner, Office, Parking

Condo in Winchcombe

4.93 out of 5 average rating, 69 reviews

The flat over the pub!

Home in Winchcombe

5 out of 5 average rating, 17 reviews

The Old Forge

Home in Winchcombe

4.99 out of 5 average rating, 72 reviews

Cottage on the Cotswold Way

Quick stats about vacation rentals in Winchcombe

Total rentals
150 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
9.9K reviews
Family-friendly rentals
100 properties are a good fit for families
Pet-friendly rentals
80 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace

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 210 vacation rentals in Greet, over 260 vacation rentals in Winchcombe, and over 210 vacation rentals in Gretton.
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 vacation rentals in Winchcombe?
Four-legged friends are welcome in Winchcombe. Choose from more than 80 vacation 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 cottage rentals in Winchcombe?
Experience the best of Winchcombe with our cottage rentals, starting at about $80 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 vacation rentals in Winchcombe?
Winchcombe has more than 100 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Cottage Rentals in Winchcombe?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 60 homes with wifi, over 40 homes with free parking, over 60 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there vacation rentals with a dedicated workspace in Winchcombe?
Yes! Work meets play with ease at over 50 vacation rentals in Winchcombe featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore