Cheltenham Vacations from $698

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Gloucester Robinswood Hotel, BW Signature Collection

Gloucester Robinswood Hotel, BW Signature Collection

4 out of 5
Price was $831, price is now $698 per person
$698
per person
Oct 26 - Nov 1
found 2 days ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Birmingham (BHX)
7.6/10 Good! (1,003 reviews)
Won a bid for room upgrade but when booking in none available. No biscuits with tea tray. Definitely overrated hotel.

Reviewed on Aug 13, 2025

Comfy, 2 Bed House, Sleeps 6 with Garden and Free Parking in Cheltenham

Comfy, 2 Bed House, Sleeps 6 with Garden and Free Parking in Cheltenham

3.5 out of 5
Price was $1,412, price is now $1,168 per person
$1,168
per person
Oct 12 - Oct 17
found 11 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Birmingham (BHX)
No reviews
Cozy Cotswolds Retreat in Dursley

Cozy Cotswolds Retreat in Dursley

2 out of 5
Price was $1,642, price is now $1,408 per person
$1,408
per person
Oct 26 - Nov 1
found 2 days ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Birmingham (BHX)
No reviews
The Mount Pleasant Hotel

The Mount Pleasant Hotel

3 out of 5
Price was $1,482, price is now $1,275 per person
$1,275
per person
Oct 12 - Oct 17
found 11 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Birmingham (BHX)
8.2/10 Very Good! (308 reviews)
Traditional villas, appartments around a village green. The inside of the apartments has been nicely updated. the reception area needs an professional update.

Reviewed on Jul 24, 2025

Stunning Townhouse in Cirencester

Stunning Townhouse in Cirencester

2 out of 5
Price was $1,684, price is now $1,449 per person
$1,449
per person
Oct 12 - Oct 17
found 11 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Birmingham (BHX)
No reviews
Don't see what you're looking for?
See all available trips from Columbus to Cheltenham
View all trips

Discover the most popular places to visit in Cheltenham

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 Cheltenham

Classic Cotswolds – Online Self-Guided Road Trip Plan

Classic Cotswolds – Online Self-Guided Road Trip Plan

$17
per traveler
Classic Cotswolds – Online Self-Guided Road Trip Plan
Scenic Transfer from Stratford Upon Avon to London Via Cotswolds

Scenic Transfer from Stratford Upon Avon to London Via Cotswolds

$120
per adult
Scenic Transfer from Stratford Upon Avon to London Via Cotswolds
Blenheim Palace and Cotswolds Private Tour

Blenheim Palace and Cotswolds Private Tour

$1,061
per traveler
Blenheim Palace and Cotswolds Private Tour
See all activities in Cheltenham

Cheltenham Hotel Deals

Cheltenham Chase Hotel & Spa

Cheltenham Chase Hotel & Spa

4 out of 5
Shurdington Road, Brockworth, Cheltenham, England
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $109 total per night from Sep 22 to Sep 23
$109 total
Sep 22 - Sep 23
Total with taxes and fees
8.2/10 Very Good! (1,002 reviews)
"Was excellent stay room good size and comfortable. Alex at breakfast was brilliant"

Reviewed on Aug 22, 2025

Cheltenham Chase Hotel & Spa
Ellenborough Park

Ellenborough Park

5 out of 5
Southam Road, Cheltenham, England
Fully refundableReserve now, pay when you stay
$303 nightly
The price is $364 total per night from Aug 31 to Sep 1
$364 total
Aug 31 - Sep 1
Total with taxes and fees
9/10 Wonderful! (538 reviews)
"Lovely hotel with beautiful rooms and accommodations. The room and bathroom were extremely large and beautifully appointed. We ate at the restaurant one evening and the food and ambiance was great. We will definitely stay here again when we return!"

Reviewed on Aug 21, 2025

Ellenborough Park
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 Aug 31 to Sep 1
$103 total
Aug 31 - Sep 1
Total with taxes and fees
8.2/10 Very Good! (1,002 reviews)
"Amazing reception, great gym, perfect breakfast, but no air con and pillow (both available) quite big."

Reviewed on Aug 12, 2025

Leonardo Hotel Cheltenham
See all 1,119 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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Cheltenham vacation package cost?
You can snap up a vacation package to this popular destination from $698 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.