A traditional Tudor-style building with a 'Wesley House' sign, a wine bar, and a restaurant.

Winchcombe Holiday Rentals

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Our top choices for Winchcombe holiday rentals

1. Cosy Cotswold Stone Cottage with wood burner and 2.5 bathrooms

Cosy Cotswold Stone Cottage with wood burner and 2.5 bathrooms
Winchcombe
9.8 out of 10, Exceptional, (97 reviews)
"We had a wonderful stay lovely cottage well located everything you could need is provided would highly recommend"
Australia
martyn s.
The price is NZ$428
includes taxes & fees
1 Dec - 2 Dec
Cosy Cotswold Stone Cottage with wood burner and 2.5 bathrooms

2. Old Sorting Office

Old Sorting Office
3.5 star property
Cheltenham
10.0 out of 10, Exceptional, (2 reviews)
"Great location in the heart of Winchcombe but tucked away and private. A well equipped cottage with washing machine and dishwasher, lovely big bed, comfortable lounge and a courtyard garden. There was a somw noise from the pub garden two doors down, particularly when they had a live band on, but it didnt go on too late. The bath was one of those with an accessible door on it so you can walk in and a hoist which made it a little strange , but shower was fine. Great stay. Will stay again."
United Kingdom
Sarah
The price is NZ$1,071
includes taxes & fees
15 Nov - 16 Nov
Old Sorting Office

3. Thimble Cottage

Thimble Cottage
3.5 star property
Cheltenham
The price is NZ$1,484
includes taxes & fees
18 Nov - 19 Nov
Thimble Cottage

4. Strozzi Palace Suites by Mansley

Strozzi Palace Suites by Mansley
4.0 star property
Cheltenham
9.4 out of 10, Exceptional, (254 reviews)
"Everything we hoped for and more. If the parking was more straightforward it would be 100% . But Everything worked ."
United Kingdom
Roy
The price is NZ$173
includes taxes & fees
16 Nov - 17 Nov
Strozzi Palace Suites by Mansley

5. George Apartments

George Apartments
2.0 star property
Broadway
9.2 out of 10, Wonderful, (59 reviews)
"A very nice place to stay"
Canada
Peter
The price is NZ$307
includes taxes & fees
6 Dec - 7 Dec
George Apartments

6. Crescent Place by Mansley

Crescent Place by Mansley
3.0 star property
Cheltenham
9.4 out of 10, Exceptional, (158 reviews)
"Fabulous location. Brilliant room and facilities. Great value."
United Kingdom
Simon
The price is NZ$172
includes taxes & fees
8 Nov - 9 Nov
Crescent Place by Mansley

7. The Lodge at Bredon's Norton

The Lodge at Bredon's Norton
2.0 star property
Tewkesbury
10.0 out of 10, Exceptional, (1 review)
The price is NZ$235
includes taxes & fees
8 Nov - 9 Nov
The Lodge at Bredon's Norton

8. 21 Montpellier Terrace

21 Montpellier Terrace
3.0 star property
The Suffolks
9.6 out of 10, Exceptional, (8 reviews)
"Amazing place right at the heart of centre. Great how who communicate well. Effortless Stay."
United Kingdom
Tarun
The price is NZ$450
includes taxes & fees
11 Nov - 12 Nov
21 Montpellier Terrace

9. Portland Apartments

Portland Apartments
3.5 star property
Cheltenham
9.8 out of 10, Exceptional, (156 reviews)
"Perfect location and beautiful accommodation"
United Kingdom
Helen
The price is NZ$300
includes taxes & fees
7 Dec - 8 Dec
Portland Apartments

10. Stunning 3 Bedroom Cotswold Retreat

Stunning 3 Bedroom Cotswold Retreat
2.0 star property
Broadway
The price is NZ$2,064
includes taxes & fees
16 Nov - 17 Nov
Stunning 3 Bedroom Cotswold Retreat

11. Cotswold Townhouse - Adults Only

Cotswold Townhouse - Adults Only
2.5 star property
Stow-on-the-Wold
The price is NZ$479
includes taxes & fees
15 Nov - 16 Nov
Cotswold Townhouse - Adults Only

12. The Vale Golf and Country Club

The Vale Golf and Country Club
3.0 star property
Pershore
8.8 out of 10, Excellent, (69 reviews)
"Lovely quiet location with fabulous lake views . The room was spotless . Staff friendly and helpful"
United Kingdom
Margaret
The price is NZ$221
includes taxes & fees
18 Nov - 19 Nov
The Vale Golf and Country Club

13. Little Cottage in Moreton-in-Marsh

Little Cottage in Moreton-in-Marsh
2.0 star property
Moreton-in-Marsh
10.0 out of 10, Exceptional, (3 reviews)
"Lovely little cottage, nice, clean and cosy. Great for a couple staying few nights."
United Kingdom
julian
The price is NZ$1,162
includes taxes & fees
24 Nov - 25 Nov
Little Cottage in Moreton-in-Marsh

14. 🌿 Countryside Escape – Chic Tiny Home in the Heart of the Cotswolds

🌿 Countryside Escape – Chic Tiny Home in the Heart of the Cotswolds
Blockley
9.2 out of 10, Wonderful, (7 reviews)
"Stayed here for four weeks in a row & simply my favourite place to stay, lovely Cotswolds village."
United Kingdom
Tom F.
🌿 Countryside Escape – Chic Tiny Home in the Heart of the Cotswolds

15. Windsor Cottage-Bolthole in heart of CN

Windsor Cottage-Bolthole in heart of CN
3.0 star property
Chipping Norton
9.6 out of 10, Exceptional, (5 reviews)
"We loved our stay in Chipping Norton, the place was perfect size for our party of 3, great location, and ridiculously cute :) only wished we could have stayed longer."
Canada
Diane
The price is NZ$468
includes taxes & fees
18 Nov - 19 Nov
Windsor Cottage-Bolthole in heart of CN

16. Cosy Cowshed Retreat, Snug Hideaway Nestled in the Heart of Campden

Cosy Cowshed Retreat, Snug Hideaway Nestled in the Heart of Campden
Chipping Campden
9.8 out of 10, Exceptional, (10 reviews)
"Great location!"
Canada
Sigal
The price is NZ$521
includes taxes & fees
2 Dec - 3 Dec
Cosy Cowshed Retreat, Snug Hideaway Nestled in the Heart of Campden

17. Old Fleece Apartments

Old Fleece Apartments
3.5 star property
Stroud
8.8 out of 10, Excellent, (44 reviews)
"Was fab . Breakfast was delicious ."
United Kingdom
Charlotte
The price is NZ$190
includes taxes & fees
15 Nov - 16 Nov
Old Fleece Apartments

18. Elliot Oliver - Deluxe Two Bedroom Apartment With Parking & EV Charger

Elliot Oliver - Deluxe Two Bedroom Apartment With Parking & EV Charger
3.5 star property
Cheltenham
8.4 out of 10, Very good, (5 reviews)
"The property was so comfy ,easy to self check in.clean and convenience location. Our family had a great time here."
Hong Kong SAR China
heiyu
The price is NZ$530
includes taxes & fees
21 Nov - 22 Nov
Elliot Oliver - Deluxe Two Bedroom Apartment With Parking & EV Charger

19. Stow on the Wold Scandi Chic Authentic Cottage

Stow on the Wold Scandi Chic Authentic Cottage
Stow-on-the-Wold
10.0 out of 10, Exceptional, (11 reviews)
"Excellent choice for Stow and the Cotswolds.. loved the cottage and the host is v friendly and informative."
United Kingdom
Pete
The price is NZ$628
includes taxes & fees
8 Nov - 9 Nov
Stow on the Wold Scandi Chic Authentic Cottage

20. Recently converted self-contained apartment with garden in Cotswold village

Recently converted self-contained apartment with garden in Cotswold village
Poulton
9.0 out of 10, Wonderful, (51 reviews)
"The location was convenient as a base for exploring Cotswolds. The guesthouse was small for a family of three, but it had everything we needed. We would definitely consider booking this property if we visit this area again."
United States
Walter
The price is NZ$187
includes taxes & fees
6 Dec - 7 Dec
Recently converted self-contained apartment with garden in Cotswold village
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winchcombe Hotel Reviews

Find out more about Winchcombe

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Winchcombe holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Winchcombe. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Winchcombe. Seeing all the best attractions is bound to make you fall in love with Winchcombe. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Winchcombe short-term rentals, that won’t be hard to do.

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Frequently asked questions

Are there holiday rentals in Winchcombe?

Yes, there are holiday rentals close to the most popular sights in Winchcombe, or you can select a more secluded option if you're looking for a relaxing stay. Winchcombe is known for its museums and restaurants.

What are some of the best holiday rentals that Winchcombe has to offer?

Charming Victorian Wool Cottage on the Cotswold Way in Winchcombe.: This highly rated holiday home rental in Winchcombe is located in a rural location, and has a fireplace, a furnished patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a terrace, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Winchcombe?

Expedia has 15 holiday rentals for your stay in Winchcombe.

What’s there to see and do in Winchcombe?

While exploring the area, visit family-friendly sights like Cotswold Farm Park, or get outside and enjoy nature at Pittville Park. In the wider area, you’ll find St Peter's Church Winchcombe and Winchcombe Folk and Police Museum.

What’s a holiday rental in Winchcombe like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchcombe. Holiday rentals feature extras such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for a family trip or a small group gathering.