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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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
3.0 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
$453 nightly
The price is $543
Oct 11 - Oct 12
Total with taxes and fees
Old Sorting Office
A dining table set with white plates, bowls, and cutlery, surrounded by blue chairs.

2. 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
$687 nightly
The price is $687
Sep 30 - Oct 1
Total with taxes and fees
Charming Cotswold Cottage in Central Winchcombe
A stone building with a sign for 'The Lion Inn' and a visible entrance.

3. Thimble Cottage

Thimble Cottage
3.5 star property
Cheltenham
$627 nightly
The price is $753
Sep 27 - Sep 28
Total with taxes and fees
Thimble Cottage
A bedroom with a bed, bedside tables, a chair, a window, and a radiator.

4. George Apartments

George Apartments
2.0 star property
Broadway
9.4 out of 10, Exceptional, (55 reviews)
"Excellent location and well stocked kitchen."
United States
Elisa
$115 nightly
The price is $138
Sep 24 - Sep 25
Total with taxes and fees
George Apartments
A building with a black door, a staircase leading to an upper floor, and a signboard for 'crescent place' with a website address.

5. Crescent Place by Mansley

Crescent Place by Mansley
3.0 star property
Cheltenham
9.2 out of 10, Wonderful, (140 reviews)
"Lovely, very clean and great location"
United Kingdom
Nina
$97 nightly
The price is $116
Oct 18 - Oct 19
Total with taxes and fees
Crescent Place by Mansley
A hotel lobby with a staircase, a chandelier, a vase with flowers, and a framed picture on the wall.

6. Strozzi Palace Suites by Mansley

Strozzi Palace Suites by Mansley
4.0 star property
Cheltenham
9.4 out of 10, Exceptional, (246 reviews)
"Very nice hotel. Great stay."
United States
Thomas
$94 nightly
The price is $113
Sep 27 - Sep 28
Total with taxes and fees
Strozzi Palace Suites by Mansley
A dining table with a bowl and two wine glasses, a fork, and a spoon.

7. 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
$95 nightly
The price is $95
Oct 4 - Oct 5
Total with taxes and fees
Spa Court
A beige building with a black door, a small set of steps, and two potted plants.

8. Portland Apartments

Portland Apartments
3.5 star property
Cheltenham
9.8 out of 10, Exceptional, (154 reviews)
"Fantastic accommodation."
United Kingdom
Helen
$126 nightly
The price is $152
Oct 12 - Oct 13
Total with taxes and fees
Portland Apartments
A spacious living room with a fireplace, comfortable seating, a dining area, and large windows offering a view of the outdoors.

9. 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.
$274 nightly
The price is $274
Sep 24 - Sep 25
Total with taxes and fees
Beautiful & spacious Regency apt in centre Cheltenham, free parking
A lakeside cabin with a dock extending into the water, surrounded by trees and a clear sky.

10. The Vale Golf and Country Club

The Vale Golf and Country Club
3.0 star property
Pershore
8.8 out of 10, Excellent, (67 reviews)
"Excellent pricing. Note your cabin booking doesn't include Breakfast but that was ideal for our party in midweek. The rates are so preferable for really beautiful albeit compact accommodation with great views and convenience. Would book again and the golf course was in superb condition despite the heatwave(s)!"
United Kingdom
Mark
$115 nightly
The price is $138
Sep 27 - Sep 28
Total with taxes and fees
The Vale Golf and Country Club
A two-story building with a symmetrical facade, large windows, and a central entrance with a door.

11. 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
$262 nightly
The price is $315
Sep 24 - Sep 25
Total with taxes and fees
Mayville House Apartment
A wooden picnic table with a tray of green and white cups and a small potted plant.

12. Swallow Studio

Swallow Studio
3.0 star property
Cheltenham
$445 nightly
The price is $534
Sep 27 - Sep 28
Total with taxes and fees
Swallow Studio
A cozy living room with a stone fireplace, wicker baskets, a striped sofa, and a window with a view of greenery.

13. Broadway Scandi Chic Cottage

Broadway Scandi Chic Cottage
Broadway
9.8 out of 10, Exceptional, (7 reviews)
"Great design and feel. Easy walks around town. Fun hike from the cottage, about 45 minutes, up to Broadway Tower."
United States
Brian S.
$378 nightly
The price is $378
Oct 1 - Oct 2
Total with taxes and fees
Broadway Scandi Chic Cottage
A stone building with a wooden fence, a potted plant, and a black object on the ground.

14. 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)
"Amazing apartment. Great communication. Only thing missing was a couple of little side tables next to settee for drinks but would definitely stay again. Highly recommended!!"
United Kingdom
Karen
$370 nightly
The price is $370
Oct 4 - Oct 5
Total with taxes and fees
Brand New 2-Bed, Dog-Friendly Apartment | Broadway High St | Sleeps 6
A spacious living room with a leather sofa, a coffee table with a tray, and a wooden cabinet.

15. The Judges Lodgings Boutique Hotel

The Judges Lodgings Boutique Hotel
3.5 star property
Gloucester
9.0 out of 10, Wonderful, (18 reviews)
"The apartment was brilliant grrat bathrooms and the bed was amazingly comfortable, the kitch area was brilliant "
United Kingdom
Andrew
$163 nightly
The price is $195
Oct 11 - Oct 12
Total with taxes and fees
The Judges Lodgings Boutique Hotel

16. 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
$260 nightly
The price is $312
Oct 17 - Oct 18
Total with taxes and fees
Elliot Oliver - Deluxe Two Bedroom Apartment With Parking & EV Charger
A hotel room with a bed, a sofa, a small table, a chair, a desk, a lamp, a picture on the wall, and a window with blinds.

17. The Cozy Apartment

The Cozy Apartment
2.0 star property
Gloucester
7.6 out of 10, Good, (19 reviews)
"Suited our needs perfectly for our short stay to take part in Gloucester half marathon. "
United Kingdom
Matt
$110 nightly
The price is $132
Sep 27 - Sep 28
Total with taxes and fees
The Cozy Apartment
The Bantam Tea Rooms with a large display window, a tea garden sign, and a door with a sign indicating it's open.

18. Camside, Chipping Campden - Taswell Retreats

Camside, Chipping Campden - Taswell Retreats
4.0 star property
Chipping Campden
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful and well maintained cottage. Would love to visit again."
United States
Brent
$195 nightly
The price is $235
Oct 7 - Oct 8
Total with taxes and fees
Camside, Chipping Campden - Taswell Retreats
A modern kitchen with dark cabinets and a dining area with a glass table.

19. Elliot Oliver - Luxurious 2 Bedroom Apartment With Parking

Elliot Oliver - Luxurious 2 Bedroom Apartment With Parking
3.5 star property
Gloucester
10.0 out of 10, Exceptional, (6 reviews)
"I loved my stay here, spotless and quick responses"
United Kingdom
Macey
$206 nightly
The price is $247
Oct 3 - Oct 4
Total with taxes and fees
Elliot Oliver - Luxurious 2 Bedroom Apartment With Parking
A traditional stone house with a thatched roof, surrounded by snow-covered rocks and bare trees.

20. Cotswold Chic Retreats "Jacinabox" in Chipping Campden The Cotswolds

Cotswold Chic Retreats "Jacinabox" in Chipping Campden The Cotswolds
Chipping Campden
9.4 out of 10, Exceptional, (23 reviews)
"Lovely little cottage tucked away off the main street. All mod cons, comfy bed and sofa and nice little garden. Many shops and restaurants on the main street. A good place to stay to visit The Cotswolds."
United Kingdom
Melanie F.
$243 nightly
The price is $243
Oct 8 - Oct 9
Total with taxes and fees
Cotswold Chic Retreats "Jacinabox" in Chipping Campden The Cotswolds
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

Cheltenham Chase Hotel & Spa

Cheltenham Chase Hotel & Spa

10/10 Excellent
"Great place... lovely rooms... nice bar and outside area. Breakfast good and use of a spa. No complaints at all."
Malcolm 1-night trip
Posted 11 hours ago
Cheltenham Chase Hotel & Spa

Find out more about Winchcombe

Everything you need to know about Winchcombe vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchcombe vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchcombe vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchcombe vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchcombe. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winchcombe in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $105 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchcombe rentals

At Expedia, we put the best Winchcombe vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winchcombe rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchcombe vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchcombe. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.

What's the top vacation rental that Winchcombe has to offer?

Charming Victorian Wool Cottage on the Cotswold Way in Winchcombe.: This highly rated vacation home rental in Winchcombe is located in a rural location and has a fireplace, a furnished patio, and a barbecue grill 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 you can immerse yourself in your vacation.

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.