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

Winchcombe Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Winchcombe holiday rentals

A stone fireplace with a wood-burning stove, a stack of firewood to the left, and a television on a wooden stand to the right.

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 HK$1,729
HK$2,217 total
includes taxes & fees
19 Oct - 20 Oct
Cosy Cotswold Stone Cottage with wood burner and 2.5 bathrooms
A cozy living room with two white sofas, a flat-screen TV on a wooden stand, and a large window with curtains.

2. Old Sorting Office

Old Sorting Office
3.0 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 HK$3,522
HK$4,227 total
includes taxes & fees
3 Nov - 4 Nov
Old Sorting Office
A dining area with a round table set for four, surrounded by chairs, a vase with flowers, and a pendant light.

3. Charming Cotswold Cottage in Central Winchcombe

Charming Cotswold Cottage in Central Winchcombe
Winchcombe
10.0 out of 10, Exceptional, (1 review)
"A stunning cottage, absolutely spotless and very well equipped. I cannot recommend this place enough, great location, parking was easy. The beds were super comfortable."
United States
Steph
The price is HK$4,300
HK$4,300 total
includes taxes & fees
2 Nov - 3 Nov
Charming Cotswold Cottage in Central Winchcombe
A cozy living room with a brick fireplace, a dining area with a table set for two, and a television on a stand.

4. Cosy Tarbh Cottage with Log Burner in Winchcombe

Cosy Tarbh Cottage with Log Burner in Winchcombe
Winchcombe
Cosy Tarbh Cottage with Log Burner in Winchcombe
A wooden pergola with a hanging chair, stone walls, and a fenced garden area.

5. Cosy Teapot Cottage in Winchcombe with Log Burner

Cosy Teapot Cottage in Winchcombe with Log Burner
Winchcombe
Cosy Teapot Cottage in Winchcombe with Log Burner
A stone building with a sign for 'The Lion Inn' and a visible entrance.

6. Thimble Cottage

Thimble Cottage
3.5 star property
Cheltenham
The price is HK$4,882
HK$5,858 total
includes taxes & fees
27 Oct - 28 Oct
Thimble Cottage
A bedroom with a bed, bedside tables, a chair, a window, and a radiator.

7. George Apartments

George Apartments
2.0 star property
Broadway
9.4 out of 10, Exceptional, (56 reviews)
"Excellent location and well stocked kitchen."
United States
Elisa
The price is HK$1,030
HK$1,236 total
includes taxes & fees
13 Oct - 14 Oct
George Apartments
A hotel lobby with a staircase, a chandelier, a vase with flowers, and a framed picture on the wall.

8. Strozzi Palace Suites by Mansley

Strozzi Palace Suites by Mansley
4.0 star property
Cheltenham
9.4 out of 10, Exceptional, (249 reviews)
"Very nice hotel. Great stay."
United States
Thomas
The price is HK$770
HK$924 total
includes taxes & fees
2 Nov - 3 Nov
Strozzi Palace Suites by Mansley
A building with a black door, a staircase leading to an upper floor, and a signboard for 'crescent place' with a website address.

9. Crescent Place by Mansley

Crescent Place by Mansley
3.0 star property
Cheltenham
9.4 out of 10, Exceptional, (149 reviews)
"Lovely, very clean and great location"
United Kingdom
Nina
The price is HK$732
HK$879 total
includes taxes & fees
18 Oct - 19 Oct
Crescent Place by Mansley
A modern kitchen with a high ceiling, skylights, a dining area with a bar stool, and a seating area with two chairs.

10. Beautiful Self Contained Annex in Toddington

Beautiful Self Contained Annex in Toddington
Cheltenham
10.0 out of 10, Exceptional, (4 reviews)
"Ideal spot for Cheltenham"
United States
Calum
The price is HK$2,846
HK$2,846 total
includes taxes & fees
15 Oct - 16 Oct
Beautiful Self Contained Annex in Toddington
A beige building with a black door, a small set of steps, and two potted plants.

11. Portland Apartments

Portland Apartments
3.5 star property
Cheltenham
9.8 out of 10, Exceptional, (156 reviews)
"Fantastic accommodation."
United Kingdom
Helen
The price is HK$1,082
HK$1,298 total
includes taxes & fees
25 Oct - 26 Oct
Portland Apartments
A room with a fireplace, a television, a dining table with chairs, a sofa, and a large window with a view of greenery.

12. 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 HK$831
HK$831 total
includes taxes & fees
18 Oct - 19 Oct
21 Montpellier Terrace
A lakeside cabin with a dock extending into the water, surrounded by trees and a clear sky.

13. 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 HK$896
HK$1,075 total
includes taxes & fees
13 Oct - 14 Oct
The Vale Golf and Country Club
A spacious living room with a fireplace, comfortable seating, a dining area, and large windows offering a view of the outdoors.

14. Beautiful & spacious Regency apt in centre Cheltenham, free parking

Beautiful & spacious Regency apt in centre Cheltenham, free parking
Montpellier
9.8 out of 10, Exceptional, (21 reviews)
"Lovely property, comfortable and location is great for exploring the Cotswolds."
United Kingdom
Carol W.
The price is HK$1,506
HK$2,856 total
includes taxes & fees
29 Oct - 30 Oct
Beautiful & spacious Regency apt in centre Cheltenham, free parking
A dining table with a bowl and two wine glasses, a fork, and a spoon.

15. Spa Court

Spa Court
3.0 star property
Cheltenham
7.2 out of 10, Good, (49 reviews)
"In the centre of town .Ideal for the racecourse.Easy access,pleasant and helpful staff "
United Kingdom
Paul
The price is HK$508
HK$758 total
includes taxes & fees
25 Oct - 26 Oct
Spa Court
An open-plan living and dining area with a large sliding glass door to a backyard, a dining table set with plates and glasses, and a sofa with cushions.

16. Stunning 3 Bedroom Cotswold Retreat

Stunning 3 Bedroom Cotswold Retreat
2.0 star property
Broadway
The price is HK$5,375
HK$8,008 total
includes taxes & fees
23 Oct - 24 Oct
Stunning 3 Bedroom Cotswold Retreat
A stone building with a door, a window, and a small garden area with plants and a table.

17. 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, (2 reviews)
"Lovely little cottage, nice, clean and cosy. Great for a couple staying few nights."
United Kingdom
julian
The price is HK$3,384
HK$4,913 total
includes taxes & fees
2 Nov - 3 Nov
Little Cottage in Moreton-in-Marsh
A stone building with a wooden fence, a potted plant, and a black object on the ground.

18. Brand New 2-Bed, Dog-Friendly Apartment | Broadway High St | Sleeps 6

Brand New 2-Bed, Dog-Friendly Apartment | Broadway High St | Sleeps 6
Worcestershire
10.0 out of 10, Exceptional, (4 reviews)
"Lovely apartment in an outstanding location."
United States
Mary W.
The price is HK$1,921
HK$2,856 total
includes taxes & fees
22 Oct - 23 Oct
Brand New 2-Bed, Dog-Friendly Apartment | Broadway High St | Sleeps 6
A stone building with a white door and a small porch area with a bench and chairs.

19. Jasmine Cottage-2BD in Heart of Bourton

Jasmine Cottage-2BD in Heart of Bourton
3.0 star property
Cheltenham
10.0 out of 10, Exceptional, (5 reviews)
"Very thoughtfully prepared cozy space. We enjoyed staying there with our two daughters. The o communication was excellent and check in and out very seamless. Location is superb if desiring to stay in Burton in the water. Beautiful, quaint town. Only complaint was lack of cooling. Luckily able to cool off at night with windows open. We really enjoyed our stay. "
United States
Ryan
The price is HK$2,166
HK$3,741 total
includes taxes & fees
27 Oct - 28 Oct
Jasmine Cottage-2BD in Heart of Bourton
A neatly arranged bedroom with a large bed, two framed pictures on the wall, and a tray with a teapot and cups on the bed.

20. Luxurious 1 Bed Detached Home with Gated Parking

Luxurious 1 Bed Detached Home with Gated Parking
Cheltenham
10.0 out of 10, Exceptional, (2 reviews)
"Beautifully decorated, well appointed, comfortable bed, black out curtains for easy sleeping, good water pressure and nice hot water."
United States
Catherine
Luxurious 1 Bed Detached Home with Gated Parking
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

The Swans Nest Hotel

The Swans Nest Hotel

10/10 Excellent
"Comfortable bedroom clean ( quiet considering there were external maintenance work in progress) relaxed communal seating area. Ideal location adjacent to Bar serving meals with drinks discount for hotel guests and a popular bistro restaurant, Short walk to RSC and town centre. Excellent staff ( must give a mention manager Fiona ) friendly helpful and extremely knowledgeable about the area offering great suggestions of places to see or visit."
Steve 1-night trip
Posted 9 hours ago
The Swans Nest Hotel

Find out more about Winchcombe

Search for holiday rentals in Winchcombe on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchcombe using one of the methods below:

  • View our selection of featured holiday rentals in Winchcombe
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  • Enter your travel dates to view the best deals on holiday rentals in Winchcombe while they last

Look no further and take a look at our great range of rental properties in Winchcombe!

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.