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. 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 NZ$952
includes taxes & fees
10 Oct - 11 Oct
Old Sorting Office

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
The price is NZ$1,205
includes taxes & fees
30 Sept - 1 Oct
Charming Cotswold Cottage in Central Winchcombe

3. Thimble Cottage

Thimble Cottage
3.5 star property
Cheltenham
The price is NZ$1,320
includes taxes & fees
27 Sept - 28 Sept
Thimble Cottage

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
The price is NZ$278
includes taxes & fees
28 Sept - 29 Sept
George Apartments

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
The price is NZ$188
includes taxes & fees
18 Oct - 19 Oct
Crescent Place by Mansley

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
The price is NZ$196
includes taxes & fees
27 Sept - 28 Sept
Strozzi Palace Suites by Mansley

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
The price is NZ$164
includes taxes & fees
4 Oct - 5 Oct
Spa Court

8. Portland Apartments

Portland Apartments
3.5 star property
Cheltenham
9.8 out of 10, Exceptional, (154 reviews)
"Fantastic accommodation."
United Kingdom
Helen
The price is NZ$281
includes taxes & fees
28 Sept - 29 Sept
Portland Apartments

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.
The price is NZ$474
includes taxes & fees
24 Sept - 25 Sept
Beautiful & spacious Regency apt in centre Cheltenham, free parking

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
The price is NZ$242
includes taxes & fees
29 Sept - 30 Sept
The Vale Golf and Country Club

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
The price is NZ$552
includes taxes & fees
25 Sept - 26 Sept
Mayville House Apartment

12. Swallow Studio

Swallow Studio
3.0 star property
Cheltenham
The price is NZ$935
includes taxes & fees
26 Sept - 27 Sept
Swallow Studio

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.
The price is NZ$687
includes taxes & fees
1 Oct - 2 Oct
Broadway Scandi Chic Cottage

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
The price is NZ$648
includes taxes & fees
22 Oct - 23 Oct
Brand New 2-Bed, Dog-Friendly Apartment | Broadway High St | Sleeps 6

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
The price is NZ$335
includes taxes & fees
23 Sept - 24 Sept
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
The price is NZ$558
includes taxes & fees
17 Oct - 18 Oct
Elliot Oliver - Deluxe Two Bedroom Apartment With Parking & EV Charger

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
The price is NZ$232
includes taxes & fees
11 Oct - 12 Oct
The Cozy Apartment

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
The price is NZ$411
includes taxes & fees
7 Oct - 8 Oct
Camside, Chipping Campden - Taswell Retreats

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
The price is NZ$414
includes taxes & fees
3 Oct - 4 Oct
Elliot Oliver - Luxurious 2 Bedroom Apartment With Parking

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.
The price is NZ$419
includes taxes & fees
8 Oct - 9 Oct
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

Find out more about Winchcombe

Everything you need to know about Winchcombe holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchcombe holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winchcombe holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchcombe holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchcombe holiday rentals we have selected for you start as low as NZ$185 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchcombe rentals

At Expedia, we put the best Winchcombe holiday 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 holiday.

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. 

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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.