Winchcombe Vacations from $1,127

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Your Winchcombe Vacation

With one of our vacation packages to Winchcombe, you'll have infinite opportunities for adventure and relaxation. There's plenty to experience, including its rich history and spectacular views. Every trip to Winchcombe needs a well-crafted itinerary. Fill yours with major attractions like Cheltenham Racecourse, Sudeley Castle and The Promenade. Stop dreaming and start traveling. Check out the range of options on Expedia today and finally put your Winchcombe vacation plans in motion!

The Latest Winchcombe vacation packages

Price found within the past 48 hours. Click for updated prices.
The Charlton Boutique Hotel

The Charlton Boutique Hotel

2.5 out of 5
Price was $1,231, price is now $1,127 per person
$1,127
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Birmingham (BHX)
8.2/10 Very Good! (90 reviews)
Yes excellent services no faults

Reviewed on Oct 16, 2025

Ellenborough Park

Ellenborough Park

5 out of 5
Price was $2,074, price is now $1,805 per person
$1,805
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Birmingham (BHX)
9/10 Wonderful! (543 reviews)
I wish we had had more time to enjoy the property amenities, but the room was clean, spacious and had everything we needed. Really a luxury experience after a long day hiking the Cotswold Way. We also highly recommend the restaurant, where we had a delicious dinner and a really lovely breakfast before leaving the next morning.

Reviewed on Sep 20, 2025

Cotteswold House

Cotteswold House

2 out of 5
Price was $1,702, price is now $1,550 per person
$1,550
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Birmingham (BHX)
9.2/10 Wonderful! (20 reviews)
The house is perfectly situated just a few minutes walk to Bibury. The organisation of key collection, breakfast etc ordering was efficient. The room was cosy, with plenty of luxury amenities and lots of extra little touches. The breakfast was delicious and made to order. The only downside was the dreadful bed that was squeaky, and incredibly uncomfortable.

Reviewed on Oct 12, 2025

The Dial House

The Dial House

3.5 out of 5
Price was $1,685, price is now $1,536 per person
$1,536
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Birmingham (BHX)
9.2/10 Wonderful! (243 reviews)
Parking was good The only thing I would say is I would of liked a bigger choice of beers/lagers But our stay was marvellous

Reviewed on Oct 22, 2025

The Colesbourne Inn

The Colesbourne Inn

4 out of 5
Price was $1,279, price is now $1,167 per person
$1,167
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Birmingham (BHX)
9.2/10 Wonderful! (797 reviews)
The food menu for breakfast, lunch and dinner is amazing. Staff is friendly and knowledgeable. The inn is beautiful And we had an amazing stay.

Reviewed on Oct 20, 2025

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Discover the most popular places to visit in Winchcombe

Sudeley Castle featuring heritage architecture, a church or cathedral and a garden

Sudeley Castle

4.5/5(2 reviews)

Uncover centuries of royal history amid the halls, gardens and art exhibitions of this 15th-century castle set in the shadow of the Cotswold Hills.

Sudeley Castle
Cheltenham Town Hall

Cheltenham Town Hall

4/5(2 reviews)

Find out about the history of Cheltenham when you take a trip to Cheltenham Town Hall. Wander the area's picturesque gardens or simply enjoy one of its top-notch restaurants.

Cheltenham Town Hall
The Model Village which includes interior views

The Model Village

Walk amid a scale model replica of the shops, houses and historic landmarks that were present in Bourton-on-the-Water during the 1930s.

The Model Village

What to do in Winchcombe

Travel the back roads in one of our comfy 16-seater Mercedes minibuses - we can go where big coaches can't!

Secret Cotswolds Tour from Stratford-on-Avon or Moreton-in-Marsh

$107
per adult
Secret Cotswolds Tour from Stratford-on-Avon or Moreton-in-Marsh
Cotswolds Full-Day Tour From Birmingham

Cotswolds Full-Day Tour From Birmingham

$108
per adult
Cotswolds Full-Day Tour From Birmingham
The Cotswolds and Blenheim Palace with Lunch in British Pub

As seen in Bridgerton: Cotswold's & Blenheim Palace with Cream Tea

$146
per adult
80% of travellers recommend
As seen in Bridgerton: Cotswold's & Blenheim Palace with Cream Tea
See all activities in Winchcombe

Winchcombe Hotel Deals

De Vere Cotswold Water Park

De Vere Cotswold Water Park

4 out of 5
Lake 6 Spine Road East, South Cerney, Cirencester, England
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $143 total per night from Oct 30 to Oct 31
$143 total
Oct 30 - Oct 31
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
Great room with access to lake, plenty of space and well proportioned - spa was good, but pool could be warmer ! Breakfast nice, but you need more coffee machines. Bar area nice and cocktails superb!

Reviewed on Oct 22, 2025

De Vere Cotswold Water Park
Leonardo Hotel Cheltenham

Leonardo Hotel Cheltenham

4 out of 5
Gloucester Road, Cheltenham, England
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $102 total per night from Oct 30 to Oct 31
$102 total
Oct 30 - Oct 31
Total with taxes and fees
8.4/10 Very Good! (1,013 reviews)
Nice size room for 2 adults and 2 children Excellent breakfast All staff friendly and helpful Lovely pool on site Short distance by taxi or bus to town centre approx 10 minutes.

Reviewed on Oct 23, 2025

Leonardo Hotel Cheltenham
Kings Head

Kings Head

4 out of 5
24 Market Place, Cirencester, England
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $154 total per night from Oct 29 to Oct 30
$154 total
Oct 29 - Oct 30
Total with taxes and fees
8.8/10 Excellent! (683 reviews)
Really lovely hotel in a central location. Highly recommend

Reviewed on Oct 19, 2025

Kings Head
See all 3,837 properties in Winchcombe
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.

Find the Best Winchcombe Vacation Packages

Winchcombe Essential Information

Language
English
Currency
British pounds sterling
Closest Airport
Brize Norton (BZZ-RAF Brize Norton)
Population
4,500
Max Temp Winter
45ºF
Max Temp Summer
70ºF
Top Sights
Sudeley Castle, Everyman Theatre and Cotswold Motoring Museum

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Frequently asked questions

How much does a Winchcombe vacation package cost?
You can grab a vacation package to this popular destination from $1,127 on Expedia. However, how much your vacation to Winchcombe costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Winchcombe?
If you're hoping to score a cheap Winchcombe vacation package, consider traveling in August, October and December. You'll usually find lower rates on airfares and hotels during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Winchcombe?
The ideal duration for your Winchcombe vacation depends on what you'd like to do and see. Generally, a few days to a week will give you enough time to check out all the major attractions and explore some hidden gems along the way.
Is it worth booking a vacation package to Winchcombe?
Winchcombe is a good vacation destination with attractions like Sudeley Castle among the many things to keep you entertained. Whether you're traveling with the family or planning a trip with friends, a Winchcombe vacation promises fun for everyone.
How to find the best Winchcombe package deals?
Begin your search for a Winchcombe package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Winchcombe package deal straight away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Winchcombe adventure underway.
Is it cheaper to book a Winchcombe vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component separately. And you'll still enjoy the flexibility to create a customized Winchcombe vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Winchcombe?
If you have your Winchcombe vacation dates locked in, book early to snap up some terrific deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Winchcombe?

  1. Pick your dates: The things you want to do in Winchcombe and your preferred season will help you decide when to get away.
  2. Set a budget: Consider costs such as transportation, flights and meals when working out how much to save for your trip to Winchcombe. Then, select a hotel that works with your budget, whether that's a low-cost stay or a swankier retreat.
  3. Use our trip planning tool to discover Winchcombe: Research every aspect of your trip to Winchcombe with this handy planner. Invite your family and friends to collaborate on a group getaway, search for stays or things to do and make bookings.
  4. Set the duration of your trip: Start by making a list of all the attractions and activities you want to get to in Winchcombe. Then, estimate how long you'll need at each, along with any travel time.
  5. Combine your accommodations and airfare: After you've settled on your trip dates and duration, book the ideal Winchcombe vacation package for you.
  6. Add on excursions and experiences: Take a look at our dedicated travel guide to find some awesome things to do in Winchcombe. Book tickets or make reservations before you go to save time and avoid the hassle of looking for activities when you arrive.

Does Expedia offer Book Now, Pay Later Winchcombe vacation packages?
If you're anything like us, you love jet-setting around the world but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Winchcombe break across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.