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 AU$764
includes taxes & fees
9 Sept - 10 Sept
Old Sorting Office

2. Cosy Teapot Cottage in Winchcombe with Log Burner

Cosy Teapot Cottage in Winchcombe with Log Burner
Winchcombe
Cosy Teapot Cottage in Winchcombe with Log Burner

3. Thimble Cottage

Thimble Cottage
3.5 star property
Cheltenham
The price is AU$1,059
includes taxes & fees
18 Sept - 19 Sept
Thimble Cottage

4. George Apartments

George Apartments
2.0 star property
Broadway
9.4 out of 10, Exceptional, (52 reviews)
"Absolutely loved staying here. Air Conditioning was truly a luxury in the heat wave! Amazing location too."
United States
Leah
The price is AU$231
includes taxes & fees
7 Oct - 8 Oct
George Apartments

5. Crescent Place by Mansley

Crescent Place by Mansley
3.0 star property
Cheltenham
9.2 out of 10, Wonderful, (136 reviews)
"Room had our stay in Cheltenham, would definitely recommend and stay again."
United Kingdom
Lisa
The price is AU$162
includes taxes & fees
27 Sept - 28 Sept
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, (242 reviews)
"I had a lovely stay here with my mum. We had the siena suite and it was exceptionally clean and as per the photos. Was really nice to have the terrace and kitchenette aswell. We recieved a warm welcome from friendly staff who helped us up to the suite with our bags. Great central location and well priced too. Would definitely recommend!"
United Kingdom
Bridget
The price is AU$154
includes taxes & fees
4 Oct - 5 Oct
Strozzi Palace Suites by Mansley

7. 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 AU$225
includes taxes & fees
30 Sept - 1 Oct
Portland Apartments

8. Beautiful Self Contained Annex in Toddington

Beautiful Self Contained Annex in Toddington
Cheltenham
10.0 out of 10, Exceptional, (4 reviews)
"Ideal spot for Cheltenham"
United States
Calum
The price is AU$664
includes taxes & fees
13 Sept - 14 Sept
Beautiful Self Contained Annex in Toddington

9. Swallow Studio

Swallow Studio
3.0 star property
Cheltenham
The price is AU$750
includes taxes & fees
9 Sept - 10 Sept
Swallow Studio

10. Little Cottage in Moreton-in-Marsh

Little Cottage in Moreton-in-Marsh
2.0 star property
Moreton-in-Marsh
10.0 out of 10, Exceptional, (1 review)
"Lovely little cottage, nice, clean and cosy. Great for a couple staying few nights."
United Kingdom
julian
The price is AU$866
includes taxes & fees
16 Sept - 17 Sept
Little Cottage in Moreton-in-Marsh

11. The Vale Golf and Country Club

The Vale Golf and Country Club
3.0 star property
Pershore
8.6 out of 10, Excellent, (65 reviews)
"Really enjoyed the stay. Lovely view & easy to find. Would highly recommend to others & I will definitely be back again."
United Kingdom
Andrew
The price is AU$188
includes taxes & fees
13 Sept - 14 Sept
The Vale Golf and Country Club

12. Stunning 3 Bedroom Cotswold Retreat

Stunning 3 Bedroom Cotswold Retreat
2.0 star property
Broadway
Stunning 3 Bedroom Cotswold Retreat

13. 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 AU$433
includes taxes & fees
7 Sept - 8 Sept
Beautiful & spacious Regency apt in centre Cheltenham, free parking

14. The Cowshed Banham Cottages

The Cowshed Banham Cottages
2.5 star property
Bourton-on-the-Water
10.0 out of 10, Exceptional, (1 review)
"Had a lovely stay. Location was perfect. Hosts were very prompt with their responses. Property was clean, will book this place again if we ever revisit in the future."
United Kingdom
Pratigya
The price is AU$1,019
includes taxes & fees
7 Sept - 8 Sept
The Cowshed Banham Cottages

15. Central Serviced Apartments

Central Serviced Apartments
3.0 star property
Cheltenham
6.4 out of 10, (29 reviews)
"Great place to stay, very clean, walking distance to high street shops, and restaurants."
United Kingdom
Petra
The price is AU$328
includes taxes & fees
7 Sept - 8 Sept
Central Serviced Apartments

16. Beechwood Cottage Banham Cottages

Beechwood Cottage Banham Cottages
3.5 star property
Bourton-on-the-Water
10.0 out of 10, Exceptional, (1 review)
"We had the most marvelous stay. Girls weekend and we could walk to anywhere we needed to go. The property was beautiful and the hosts provided everything required for a wonderful weekend. Will definitely visit again."
United States
Michaela
The price is AU$1,314
includes taxes & fees
16 Sept - 17 Sept
Beechwood Cottage Banham Cottages

17. The Stables Banham Cottages

The Stables Banham Cottages
3.5 star property
Bourton-on-the-Water
The price is AU$1,231
includes taxes & fees
7 Sept - 8 Sept
The Stables Banham Cottages

18. Broadway Scandi Chic Cottage

Broadway Scandi Chic Cottage
Broadway
9.8 out of 10, Exceptional, (7 reviews)
"The cottage is in an excellent location - very convenient for walking into the centre of Broadway, with a great choice of cafés, bakeries and bars along the way! It was very clean and well equipped. Check-in was very straightforward, and the instructions very clear. We benefitted from beautiful weather during our stay, so were able to use the outside tables and chairs for all our meals."
United Kingdom
Sheila
The price is AU$612
includes taxes & fees
1 Oct - 2 Oct
Broadway Scandi Chic Cottage

19. Cosy Cowshed Retreat, Snug Hideaway Nestled in the Heart of Campden

Cosy Cowshed Retreat, Snug Hideaway Nestled in the Heart of Campden
Chipping Campden
9.8 out of 10, Exceptional, (9 reviews)
"Great location!"
Canada
Sigal
The price is AU$369
includes taxes & fees
27 Sept - 28 Sept
Cosy Cowshed Retreat, Snug Hideaway Nestled in the Heart of Campden

20. The Old Paper Shop

The Old Paper Shop
3.5 star property
Tewkesbury
10.0 out of 10, Exceptional, (2 reviews)
"Ours was a five night stay in The Old Paper Shop. Located on a busy road however night time noise was minimal. Once our car was parked we could walk everywhere for shopping, drinks at the pub and visiting the sites. Very comfortable bed and wonderful shower (great after a hard days walking). Kitchen was very well equipped. The key safe check in process was easy and efficient. Very much an old world charmer with lots of character, which was as I expected, cosy but perfect for two. Definitely...
Australia
Debra
The price is AU$691
includes taxes & fees
9 Sept - 10 Sept
The Old Paper Shop
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 favourite 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 depend 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 AU$141 per night. Entering your travel dates in the search wizard might find you 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.