Winchcombe Holiday Rentals

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Our top choices for Winchcombe holiday rentals

Cottage in Winchcombe

4 Star Cotswold Stone Cottage
9.8 out of 10, Exceptional, (96)
"We had a wonderful stay lovely cottage well located everything you could need is provided would highly recommend"
Australia
martyn s.
The price is NZ$331
includes taxes & fees
11 Jan - 12 Jan 2026
4 Star Cotswold Stone Cottage

Cottage in Cheltenham

Thimble Cottage
3.5 star property
The price is NZ$1,399
includes taxes & fees
3 Jan - 4 Jan 2026
Thimble Cottage
2.0 star property
The price is NZ$810
includes taxes & fees
26 Dec - 27 Dec
Charming Cotswold Cottage in Central Winchcombe

Holiday Home in Cheltenham

Old Sorting Office
3.0 star property
The price is NZ$887
includes taxes & fees
5 Jan - 6 Jan 2026
Old Sorting Office

Holiday Home in Cheltenham

Postmaster's Lodging
3.5 star property
The price is NZ$1,248
includes taxes & fees
29 Dec - 30 Dec
Postmaster's Lodging
3.0 star property
9.0 out of 10, Wonderful, (39)
"Excellent communication, spotless, warm, plenty of information, free wifi, comfortable. "
United Kingdom
BARBARA
The price is NZ$220
includes taxes & fees
1 Jan - 2 Jan 2026
The Vale Golf and Country Club

Aparthotel in Broadway

George Apartments
2.0 star property
9.6 out of 10, Exceptional, (18)
"The apartment was immaculate and really well appointed. It has everything you need for a short stay including coat hooks, which are so often missing in a hotel room! The apartment was ideally situated for the town with free parking. It has a noisy aircon/heating system which I tried and failed to turn off-otherwise perfect! "
United Kingdom
Lesley
The price is NZ$227
includes taxes & fees
4 Jan - 5 Jan 2026
George Apartments
3.5 star property
9.0 out of 10, Wonderful, (41)
"Really lovely accommodation. Staff were very friendly and helpful and made sure check in and out was easy. We went to the pub for food and it was excellent - great menu and well cooked and presented. Staff were really helpful again Lovely area for a walk or trip to the vineyard "
United Kingdom
Helen
The price is NZ$173
includes taxes & fees
18 Jan - 19 Jan 2026
The Coach House and The Stable

Apartment in Stroud

Old Fleece Apartments
3.5 star property
8.6 out of 10, Excellent, (39)
"Far better than expected for the price will use again"
United Kingdom
brian
The price is NZ$183
includes taxes & fees
11 Jan - 12 Jan 2026
Old Fleece Apartments

Apartment in Cheltenham

Strozzi Palace Suites by Mansley
4.0 star property
9.4 out of 10, Exceptional, (199)
"Excellent suites and great location!"
United Kingdom
Barrie
The price is NZ$173
includes taxes & fees
25 Jan - 26 Jan 2026
Strozzi Palace Suites by Mansley
3.0 star property
10.0 out of 10, Exceptional, (1)
"excellent location. Parking free from 3pm - 9am right outside the door. Very nicely renovated, good cooking facilities. Very friendly and helpful owner. Only downside for us was the bed is next to the wall so not so easy to get in and out of as a couple when you are old like us."
United Kingdom
Dawn
The price is NZ$225
includes taxes & fees
2 Jan - 3 Jan 2026
Gloucester - Apartment - Sleeps 2 - Parking - 97ws

Apartment in Worcester

Commandery Vaults
4.0 star property
9.6 out of 10, Exceptional, (7)
"As described perfect stay"
United Kingdom
Robin
The price is NZ$424
includes taxes & fees
4 Jan - 5 Jan 2026
Commandery Vaults

Aparthotel in Gloucester

The Cozy Apartment
2.0 star property
7.6 out of 10, Good, (19)
"Suited our needs perfectly for our short stay to take part in Gloucester half marathon. "
United Kingdom
Matt
The Cozy Apartment

Aparthotel in Cheltenham

Crescent Place by Mansley
3.0 star property
9.4 out of 10, Exceptional, (88)
"Good location, clean and nice rooms. "
United Kingdom
Jessica
The price is NZ$175
includes taxes & fees
4 Jan - 5 Jan 2026
Crescent Place by Mansley

Aparthotel in Cheltenham

Portland Apartments
3.5 star property
9.8 out of 10, Exceptional, (137)
"•Great Location •Apartment immaculate •Tastefully decorated •Friendly hosts •A luxurious home from home •Highly recommend •Complimentary Tea, Coffee, Milk, Orange Juice and Croissants "
United Kingdom
Debra
The price is NZ$296
includes taxes & fees
29 Dec - 30 Dec
Portland Apartments

Apartment in Worcester

Old Infirmary
4.5 star property
8.8 out of 10, Excellent, (147)
"Lovely stay for a couple days away for work. Comfy bed, good location and well equipped. Thanks! "
United Kingdom
Molly
The price is NZ$275
includes taxes & fees
28 Dec - 29 Dec
Old Infirmary

Cottage in Stratford-upon-Avon

Elmhurst Cottage
3.5 star property
10.0 out of 10, Exceptional, (1)
"Immaculately presented and very comfortable cottage with a fabulous relaxing and private garden. "
United Kingdom
Margaret
The price is NZ$2,713
includes taxes & fees
2 Jan - 3 Jan 2026
Elmhurst Cottage
9.6 out of 10, Exceptional, (10)
"Had a great stay. Lovely property "
United Kingdom
Lucy O.
The price is NZ$549
includes taxes & fees
1 Jan - 2 Jan 2026
Delightful detached 2 bedrooms 2 en-suites cottage in the heart of the Cotswolds
10.0 out of 10, Exceptional, (6)
"Had a lovely stay, the place was clean and tidy and the surroundings were peaceful and quiet. The next time I’m heading to the area I will definitely look to book this place again."
United Kingdom
Lain H.
The price is NZ$329
includes taxes & fees
30 Dec - 31 Dec
Shepherds Hut in the Cotswolds

Aparthotel in Gloucester

The Judges Lodgings Boutique Hotel
2.0 star property
8.4 out of 10, Very good, (7)
"The location was great and the area quiet. Convenient to train and bus, grocery, and local interests. Property was ok in cleanliness (white grout and subway tile require a LOT of maintenance) and the modern updates were poorly installed. Far too many bric-a-brac to keep dusted. Comfortable and spacious. "
United States
Erin
The price is NZ$337
includes taxes & fees
26 Dec - 27 Dec
The Judges Lodgings Boutique Hotel
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$173 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. 

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?

Cheltenham Country Retreats: This holiday home rental outside Winchcombe offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and a microwave. Another good choice for your trip to Winchcombe is Stunning BIG COTSWOLD COTTAGE + Annexe sleeps 16.

How many holiday rentals are there in Winchcombe?

Expedia has 14 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. Belas Knap and Winchcombe Folk and Police Museum are other places to visit while you're in town.

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.