Cheltenham Vacations from $766

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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.
The Crown Hotel

The Crown Hotel

3 out of 5
Price was $851, price is now $766 per person
$766
per person
Feb 16 - Feb 20
found 5 hours ago
Roundtrip flight included
New York (NYC) to Birmingham (BHX)
8.2/10 Very Good! (491 reviews)
We stayed in the family studio at The Crown Inn for a wedding at Lapstone Barn which was just 10 minutes away. The room was perfect for us, with a double and 2 single beds. The room has its own entrance away from the main building and we found it quiet and comfortable. Breakfast was great and service from all members of staff friendly and welcoming.

Reviewed on Nov 23, 2025

The Class Place

The Class Place

4 out of 5
Birmingham City Centre
Price was $1,770, price is now $1,488 per person
$1,488
per person
Mar 23 - Mar 27
found 2 hours ago
Roundtrip flight included
Dubai (DXB) to Birmingham (BHX)
8.8/10 Excellent! (18 reviews)
Great! Good location and great communication for checking in.

Reviewed on Feb 1, 2019

The President

The President

4 out of 5
Birmingham City Centre
Price was $1,825, price is now $1,592 per person
$1,592
per person
Mar 23 - Mar 27
found 2 hours ago
Roundtrip flight included
Dubai (DXB) to Birmingham (BHX)
8.8/10 Excellent! (13 reviews)
Excellent location for our stay. The apartment was clean and spacious and having secure parking was a bonus. Communication from the host was also excellent.

Reviewed on Dec 26, 2025

Hyll Hotel

Hyll Hotel

3.5 out of 5
Price was $1,179, price is now $1,032 per person
$1,032
per person
Feb 16 - Feb 20
found 5 hours ago
Roundtrip flight included
New York (NYC) to Birmingham (BHX)
9.2/10 Wonderful! (215 reviews)
Beautiful hotel, rooms were stunning, the communal areas were lovely and cosy and the breakfasts were delicious!

Reviewed on Jan 2, 2026

Clayton Hotel Birmingham

Clayton Hotel Birmingham

4 out of 5
Birmingham City Centre
Price was $1,755, price is now $1,576 per person
$1,576
per person
Mar 23 - Mar 27
found 2 hours ago
Roundtrip flight included
Dubai (DXB) to Birmingham (BHX)
8.4/10 Very Good! (1,001 reviews)
Room was nice, clean, and large, but the service was disappointing. The corridors were noisy past midnight and with takeaway food trays in the morning (930am) so floors clearly hadn't been checked. We were also surprised the bar closed at midnight on a Saturday. Staff refused to honor our Expedia "22% off" discount for breakfast but neither reception or dining at the lunch advised us of us and breakfast service made me uncomfortable, I was asked for payment while making tea rather than waiting until I was seated.

Reviewed on Dec 22, 2025

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Discover the most popular places to visit in Cheltenham

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 lively bars.

Cheltenham Town Hall
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
Chedworth Roman Villa which includes heritage elements, a house and a park

Chedworth Roman Villa

Roman-British history comes to life at the bathhouses, mosaics and museum of this ancient villa set in the picturesque Cotswold countryside.

Chedworth Roman Villa

What to do in Cheltenham

Full-Day Cotswolds Group Tour from London

Full-Day Cotswolds Group Tour from London

$104
per adult
100% of travellers recommend
Full-Day Cotswolds Group Tour from London
London Cotswolds Villages Day Trip by Minibus

London Cotswolds Villages Day Trip by Minibus

$101
per adult
London Cotswolds Villages Day Trip by Minibus
Cotswold Cottages

Villages of The Cotswolds Small-Group Tour by Luxury Mini Coach from London

$174
per adult
Villages of The Cotswolds Small-Group Tour by Luxury Mini Coach from London
See all activities in Cheltenham

Cheltenham Hotel Deals

Cheltenham Chase Hotel & Spa

Cheltenham Chase Hotel & Spa

4 out of 5
Shurdington Road Cheltenham England
Fully refundableReserve now, pay when you stay
$73 nightly
The price is $88 total per night from Feb 8 to Feb 9
$88 total
Feb 8 - Feb 9
Total with taxes and fees
8.2/10 Very Good! (1,013 reviews)
Clean room, food at buffet was good, a decent selection. Staff were friendly.

Reviewed on Jan 5, 2026

Cheltenham Chase Hotel & Spa
Queens Hotel Cheltenham

Queens Hotel Cheltenham

4 out of 5
The Promenade Cheltenham England
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $134 total per night from Jan 9 to Jan 10
$134 total
Jan 9 - Jan 10
Total with taxes and fees
8.8/10 Excellent! (1,006 reviews)
Room was clean and spacious and staff were polite. They turned off the heating at night though which made our first night unpleasant. Even though I called reception, I was provided only 1 electric heater which was not enough to heat up the room.But the next day I called again and they provided 2 ...

Reviewed on Jan 4, 2026

Queens Hotel Cheltenham
Leonardo Hotel Cheltenham

Leonardo Hotel Cheltenham

4 out of 5
Gloucester Road Cheltenham England
Fully refundableReserve now, pay when you stay
$82 nightly
The price is $98 total per night from Jan 15 to Jan 16
$98 total
Jan 15 - Jan 16
Total with taxes and fees
8.2/10 Very Good! (1,002 reviews)
Spotless large rooms, comfy beds. Great hotel & staff.

Reviewed on Jan 4, 2026

Leonardo Hotel Cheltenham
See all 1,148 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.

Find the Best Cheltenham Vacation Packages

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 $766 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

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