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

Winchcombe Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Winchcombe vacation rentals

A cozy living room with two white sofas, a flat-screen TV on a wooden stand, and a large window with curtains.

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 P28,848
P34,618 total
includes taxes & fees
Nov 3 - Nov 4
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 P39,982
P47,979 total
includes taxes & fees
Nov 8 - Nov 9
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
9.4 out of 10, Exceptional, (58 reviews)
"Excellent location and well stocked kitchen."
United States
Elisa
The price is P9,170
P11,004 total
includes taxes & fees
Oct 26 - Oct 27
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 P5,812
P6,975 total
includes taxes & fees
Nov 22 - Nov 23
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)
"Fantastic accommodation."
United Kingdom
Helen
The price is P9,144
P10,973 total
includes taxes & fees
Oct 26 - Oct 27
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, (154 reviews)
"Would stay again.They provided everything needed and more."
United States
Brianna
The price is P5,805
P6,966 total
includes taxes & fees
Nov 1 - Nov 2
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 P45,167
P66,959 total
includes taxes & fees
Nov 16 - Nov 17
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 P3,675
P5,716 total
includes taxes & fees
Nov 2 - Nov 3
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 price is P38,247
P45,896 total
includes taxes & fees
Nov 11 - Nov 12
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 P12,078
P15,906 total
includes taxes & fees
Nov 11 - Nov 12
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 P24,880
P24,880 total
includes taxes & fees
Oct 30 - Oct 31
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 P6,663
P10,972 total
includes taxes & fees
Oct 26 - Oct 27
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 P16,729
P20,074 total
includes taxes & fees
Oct 26 - Oct 27
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 P26,581
P39,978 total
includes taxes & fees
Nov 8 - Nov 9
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

Cotswolds Hotel & Spa

Cotswolds Hotel & Spa

10/10 Excellent
"Very nice stay-for-the-price in a lovely location right on the golf course & a mile or so walk from the centre of Chipping Norton. Free parking, nice spacious room with balcony, lovely breakfast & great staff. Will definitely go back again one day!"
Peter 1-night trip
Posted 2 hours ago
Cotswolds Hotel & Spa

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:

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Frequently asked questions

Are there vacation rentals in Winchcombe?

Yes, we give you a choice of vacation rentals close to popular local attractions in Winchcombe, or you can select a more remote option if you want a relaxing place to stay. Winchcombe is known for its museums and restaurants.

How many vacation rentals are there in Winchcombe?

Expedia has 15 vacation 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 larger area, you’ll find St Peter's Church Winchcombe and Winchcombe Folk and Police Museum.

What’s a vacation rental in Winchcombe like?

Vacation rentals are private properties you can book for a long or short time in Winchcombe. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy concierge desks while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.