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

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Winchcombe holiday rentals

A bedroom with a large bed, a window with curtains, a wall-mounted artwork, and a bedside table with a lamp.

1. 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 12.801.838 ₫
15.362.206 ₫ total
includes taxes & fees
5 Nov - 6 Nov
Old Sorting Office
A stone building with a sign for 'The Lion Inn' and a visible entrance.

2. Thimble Cottage

Thimble Cottage
3.5 star property
Cheltenham
The price is 18.059.736 ₫
21.671.683 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Thimble Cottage
A bedroom with a bed, bedside tables, a chair, a window, and a radiator.

3. 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 3.717.789 ₫
4.461.347 ₫ total
includes taxes & fees
29 Oct - 30 Oct
George Apartments
A hotel lobby with a staircase, a chandelier, a vase with flowers, and a framed picture on the wall.

4. Strozzi Palace Suites by Mansley

Strozzi Palace Suites by Mansley
4.0 star property
Cheltenham
9.4 out of 10, Exceptional, (253 reviews)
"Very nice hotel. Great stay."
United States
Thomas
The price is 2.356.429 ₫
2.827.714 ₫ total
includes taxes & fees
22 Nov - 23 Nov
Strozzi Palace Suites by Mansley
A beige building with a black door, a small set of steps, and two potted plants.

5. 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 3.707.065 ₫
4.448.478 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Portland Apartments
A building with a black door, a staircase leading to an upper floor, and a signboard for 'crescent place' with a website address.

6. Crescent Place by Mansley

Crescent Place by Mansley
3.0 star property
Cheltenham
9.4 out of 10, Exceptional, (156 reviews)
"Would stay again.They provided everything needed and more."
United States
Brianna
The price is 2.353.555 ₫
2.824.266 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Crescent Place by Mansley
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.

7. Stunning 3 Bedroom Cotswold Retreat

Stunning 3 Bedroom Cotswold Retreat
2.0 star property
Broadway
The price is 18.311.175 ₫
27.146.058 ₫ total
includes taxes & fees
16 Nov - 17 Nov
Stunning 3 Bedroom Cotswold Retreat
A dining table with a bowl and two wine glasses, a fork, and a spoon.

8. Spa Court

Spa Court
3.0 star property
Cheltenham
7.2 out of 10, Good, (51 reviews)
"In the centre of town .Ideal for the racecourse.Easy access,pleasant and helpful staff "
United Kingdom
Paul
The price is 1.661.383 ₫
2.489.007 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Spa Court
A stone building with a sign reading "The Bindery" at the entrance.

9. The Bindery

The Bindery
3.0 star property
Broadway
10.0 out of 10, Exceptional, (4 reviews)
"Everything was lovely"
United States
Patrick
The Bindery
A room with a fireplace, a television, a dining table with chairs, a sofa, and a large window with a view of greenery.

10. 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 4.896.774 ₫
6.448.569 ₫ total
includes taxes & fees
11 Nov - 12 Nov
21 Montpellier Terrace
A narrow alleyway with brick buildings, a covered walkway, and small planters along the path.

11. Elliot Oliver - Stylish 2 Bedroom Town Centre Apartment

Elliot Oliver - Stylish 2 Bedroom Town Centre Apartment
4.0 star property
Cheltenham
9.2 out of 10, Wonderful, (27 reviews)
"Lovely apartment in the centre of Cheltenham. Very clean. Check in and out was very easy. Great communication with the owners. Highly recommend."
United Kingdom
Christopher
Elliot Oliver - Stylish 2 Bedroom Town Centre Apartment
A balcony with a table and chairs, a view of the cityscape, and a door leading to an interior space.

12. Elliot Oliver - Luxury 3 Bedroom Town Centre Apartment With Parking

Elliot Oliver - Luxury 3 Bedroom Town Centre Apartment With Parking
4.0 star property
Cheltenham
9.8 out of 10, Exceptional, (17 reviews)
"Great apartment, spacious and very clean. Close to shops, restaurants and pubs "
United Kingdom
Nikki
The price is 10.086.665 ₫
10.086.665 ₫ total
includes taxes & fees
30 Oct - 31 Oct
Elliot Oliver - Luxury 3 Bedroom Town Centre Apartment With Parking
A bedroom with a bed, a yellow sofa, a brick fireplace, and a wooden ceiling beam.

13. Old Infirmary

Old Infirmary
4.5 star property
Worcester
9.0 out of 10, Wonderful, (161 reviews)
"Great location, central and with free parking! It was spacious, comfy and a fantastic shower!!!"
United Kingdom
Michelle
The price is 2.586.324 ₫
4.310.540 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Old Infirmary
A two-story building with a symmetrical facade, large windows, and a central entrance with a door.

14. Mayville House Apartment

Mayville House Apartment
3.5 star property
Cheltenham
8.8 out of 10, Excellent, (5 reviews)
"I booked this apartment for my family of 4 on the day and because we were so caught up in our trip we forgot to notify the host. We arrived in the evening and despite us not having given them a heads up first, the apartment was sorted and in impeccable state. The bed was extremely comfortable, kitch and bathroom very clean. Very happy with our overnight stay, would highly recommend.l"
United Kingdom
Boya
The price is 6.782.032 ₫
8.138.300 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Mayville House Apartment
A dining area with a wooden table and chairs, a vase of flowers, and a mirror on the wall.

15. The Haybarn Banham Cottages

The Haybarn Banham Cottages
3.5 star property
Bourton-on-the-Water
10.0 out of 10, Exceptional, (1 review)
"Great place to stay!"
United States
Velia
The price is 11.149.816 ₫
16.655.790 ₫ total
includes taxes & fees
8 Nov - 9 Nov
The Haybarn Banham Cottages
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 Lygon Arms

The Lygon Arms

10/10 Excellent
"Amazing hotel with great food. Gary the porter was superb and clearly loved his job and was very engaging. Bar area was very relaxing although very cold at times. Great location for exploring the area. Only downside was the location of car park 2 especially when it was raining with gale force winds. Definitely would recommend the hotel and will certainly go back to one of the courtyard classic rooms which were very cosy and really good size."
Chris 2-night trip
Posted 5 hours ago
The Lygon Arms

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.

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.