Cheltenham Vacations from $788

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Your Cheltenham Vacation

Say goodbye to the worries of planning and hello to a Cheltenham vacation package. With everything organized before you go, you can focus on discovering the best of this city, starting with Montpellier, which is good for bars and pubs, dining and cafes. Make your trip to Cheltenham even more fun and exciting by going sightseeing. Cheltenham Racecourse, Sudeley Castle and Cheltenham Town Hall are some of the top attractions worth exploring. Whoever you're heading away with and whatever your bank balance, your dream Cheltenham vacation is just clicks away with Expedia.

The Latest Cheltenham vacation packages

Price found within the past 48 hours. Click for updated prices.
Wychnor Park Country Club

Wychnor Park Country Club

4 out of 5
Price was $955, price is now $788 per person
$788
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Birmingham (BHX)
9.2/10 Wonderful! (421 reviews)
Wonderful room with plenty of relaxing amenities

Reviewed on Sep 20, 2025

Charles Hope Birmingham Westside

Charles Hope Birmingham Westside

3.5 out of 5
Westside
Price was $1,527, price is now $1,165 per person
$1,165
per person
Nov 24 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Birmingham (BHX)
No reviews
The President

The President

4 out of 5
Birmingham City Centre
Price was $1,630, price is now $1,251 per person
$1,251
per person
Dec 19 - Dec 24
found 1 day ago
Roundtrip flight included
New York (JFK) to Birmingham (BHX)
8.8/10 Excellent! (13 reviews)
Nice communications from the property and good location. Nice clean property, we enjoyed out stay here.

Reviewed on May 25, 2023

The Class Place

The Class Place

4 out of 5
Birmingham City Centre
Price was $1,654, price is now $1,332 per person
$1,332
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Birmingham (BHX)
8.8/10 Excellent! (18 reviews)
Great! Good location and great communication for checking in.

Reviewed on Feb 1, 2019

The Grand Hotel Birmingham

The Grand Hotel Birmingham

4 out of 5
Birmingham City Centre
Price was $2,295, price is now $1,869 per person
$1,869
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Birmingham (BHX)
9.4/10 Exceptional! (1,061 reviews)
Lovely hotel and close to all amenities. Loved Madeline Bar and Isaacs.

Reviewed on Oct 6, 2025

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Discover the most popular places to visit in Cheltenham

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

Sudeley Castle

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

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 Cheltenham

Cotswolds Full-Day Tour From Birmingham

Cotswolds Full-Day Tour From Birmingham

$109
per adult
Cotswolds Full-Day Tour From Birmingham
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

$109
per adult
Secret Cotswolds Tour from Stratford-on-Avon or Moreton-in-Marsh
The Cotswolds and Blenheim Palace with Lunch in British Pub

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

$149
per adult
80% of travellers recommend
As seen in Bridgerton: Cotswold's & Blenheim Palace with Cream Tea
See all activities in Cheltenham

Cheltenham Hotel Deals

Queens Hotel Cheltenham

Queens Hotel Cheltenham

4 out of 5
The Promenade, Cheltenham, England
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $150 total per night from Nov 2 to Nov 3
$150 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
"Staff were really lovely and welcoming. The only gripe we had is that the room and bathroom were cold,"

Reviewed on Sep 30, 2025

Queens Hotel Cheltenham
Cheltenham Chase Hotel & Spa

Cheltenham Chase Hotel & Spa

4 out of 5
Shurdington Road, Brockworth, Cheltenham, England
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $103 total per night from Nov 2 to Nov 3
$103 total
Nov 2 - Nov 3
Total with taxes and fees
8.2/10 Very Good! (1,020 reviews)
"2 night stay. Very nice hotel, took advantage of the facilities all of which very good. Hotel staff helpful with commuting in and out of Cheltenham via bus links. The only disappointment was the price of breakfast, £17. Coffe was poor and from a machine. Personally I’d expect better for the price. ..."

Reviewed on Oct 2, 2025

Cheltenham Chase Hotel & Spa
Leonardo Hotel Cheltenham

Leonardo Hotel Cheltenham

4 out of 5
Gloucester Road, Cheltenham, England
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $103 total per night from Oct 12 to Oct 13
$103 total
Oct 12 - Oct 13
Total with taxes and fees
8.2/10 Very Good! (1,004 reviews)
"Excellent hotel. Would definitely stay here again. Staff were all excellent & very friendly. Breakfast & evening meal lovely. Only fault was 1 member of staff when checking in for which previous feedback was given who just wasn’t very friendly. But this didn’t spoil our visit & would definitely recommend ..."

Reviewed on Oct 5, 2025

Leonardo Hotel Cheltenham
See all 1,123 properties in Cheltenham
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.

Cheltenham Essential Information

Language
English
Currency
British pounds sterling
Population
116,400
Max Temp Winter
45ºF
Max Temp Summer
70ºF
Top Sights
Sudeley Castle, Gloucester Cathedral and Everyman Theatre

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Frequently asked questions

How much does a Cheltenham vacation package cost?
You can snap up a vacation package to this popular destination from $788 on Expedia. However, how much your vacation to Cheltenham costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Cheltenham?
You can typically find reduced prices and better availability in November, December and January. Explore our cheap Cheltenham vacation packages and you could score some excellent off-season deals.
How many days is enough for Cheltenham?
We recommend planning a Cheltenham vacation for a minimum of 2 days. This will give you enough time to check off top sights including Cheltenham Playhouse and Winchcombe Folk and Police Museum, and explore neighborhoods like Shurdington and Birdlip. You could even slot in one or two day trips outside of Cheltenham.
Is it worth booking a vacation package to Cheltenham?
Cheltenham is a good vacation destination with attractions like Cheltenham Racecourse among the many things to keep you entertained. Whether you're traveling with the family or getting away with friends, a Cheltenham vacation promises a good time for everyone.
How to find the best Cheltenham package deals?
Use Expedia's filter tool to help you find some tempting Cheltenham package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or browse for Cheltenham package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Cheltenham vacation as a package?
You can enjoy significant savings on your next Cheltenham getaway by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to browse the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Cheltenham?
Land incredible discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Cheltenham vacation.
How to plan a trip to Cheltenham?

  1. Choose your dates: What you want to do in Cheltenham and your preferred season will help you decide when to travel.
  2. Budget wisely: On top of the price of your hotel, you should factor in other expenses. These include transportation, flights and food. Also, put aside a little extra for unexpected expenses that may crop up during your trip to Cheltenham.
  3. Discover Cheltenham using Expedia's trip planning tool: Gain insights into the top attractions and best stays for your trip to Cheltenham. You can also save your favorite places, collaborate with family and friends and organize all your plans in one place.
  4. Determine how many days away: Start by listing all the attractions you'd like to get to in Cheltenham. Then, estimate how long you'll need for each, including any travel time.
  5. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a customized Cheltenham vacation package.
  6. Book activities and experiences in advance: Whether it's a ticket to a major attraction or a walking tour, you won't have to worry about missing out on Cheltenham's highlights. Find all the fun things to do in Cheltenham with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Cheltenham vacation packages?
Your Cheltenham trip is meant to be a relaxing escape from your daily routine, not a reason for money-related stress. So to give you a little more flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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