Cheltenham Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Cheltenham

Leonardo Hotel Cheltenham

Leonardo Hotel Cheltenham

4 out of 5
Gloucester Road, Cheltenham, England
Fully refundableReserve now, pay when you stay
The price is S$135 per night from 17 Aug to 18 Aug
S$135
17 Aug - 18 Aug
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
Great hotel close to M5.
"Great hotel close to M5, easy access, clean with a great restaurant"

Reviewed on 22 Jul, 2025

Leonardo Hotel Cheltenham
The George

The George

3.5 out of 5
Saint George's Road, Cheltenham, England
Fully refundableReserve now, pay when you stay
The price is S$134 per night from 10 Aug to 11 Aug
S$134
10 Aug - 11 Aug
includes taxes & fees
8.8/10 Excellent! (568 reviews)
"Beautiful old hotel. We loved our stay here. Highly recommend it."

Reviewed on 25 Jul, 2025

The George
DoubleTree by Hilton Cheltenham-Cotswolds

DoubleTree by Hilton Cheltenham-Cotswolds

4 out of 5
Cirencester Road, Charlton Kings, Cheltenham, England
The price is S$140 per night from 21 Aug to 22 Aug
S$140
21 Aug - 22 Aug
includes taxes & fees
7.8/10 Good! (1,004 reviews)
"We had a lovely night at this hotel when attending one night at the 2000 Trees festival nearby. The girl at front desk was very friendly and helpful. We used the gym, pool, sauna and steam rooms. All were very clean. Our room was soa ious enough for 3 adults. The air con was very welcome in the 30 ..."

Reviewed on 15 Jul, 2025

DoubleTree by Hilton Cheltenham-Cotswolds
See all 1,113 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.

Popular places to visit

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

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
Pitville Pump Room showing theatre scenes and interior views

Pitville Pump Room

Marvel at the elegance of this fine Regency building, sample natural spa water, attend classical music concerts and relax on perfectly groomed lawns.

Pitville Pump Room
Cheltenham Art Gallery and Museum featuring interior views

Cheltenham Art Gallery and Museum

Discover interesting items from the stories of Cheltenham’s local heroes, to works by Dutch masters and ancient treasures in the villages of Gloucestershire.

Cheltenham Art Gallery and Museum

What to do in Cheltenham

Scenic Transfer from Stratford Upon Avon to London Via Cotswolds

Scenic Transfer from Stratford Upon Avon to London Via Cotswolds

S$154
per adult
Scenic Transfer from Stratford Upon Avon to London Via Cotswolds
Classic Cotswolds – Online Self-Guided Road Trip Plan

Classic Cotswolds – Online Self-Guided Road Trip Plan

S$23
per traveller
Classic Cotswolds – Online Self-Guided Road Trip Plan
Bourton-on-the-Water

Private One Day Luxury Tour of The Cotswolds

S$1,615
per traveller
Private One Day Luxury Tour of The Cotswolds
See all activities in Cheltenham

Frequently asked questions

How much does a Cheltenham holiday package cost?
You can snap up a holiday package to this popular destination on Expedia. However, how much your holiday 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?
If you'd like to score a cheap Cheltenham holiday package, consider visiting in December, January and February. You'll generally find better rates on hotels and airfares during these months — ideal for travellers wishing to save money.
How many days is enough for Cheltenham?
To fully enjoy a Cheltenham holiday, we suggest booking for 2 days. Divide your time between visiting Cheltenham Playhouse, Winchcombe Folk and Police Museum and other must-see attractions, on top of experiencing neighbourhoods like Barnwood and Shurdington. If you've got some time to spare, add a tour or day trip to your Cheltenham holiday itinerary.
Is it worth booking a holiday package to Cheltenham?
It's no wonder a Cheltenham holiday is on the must-do list of many travellers. Major attractions like Cheltenham Racecourse are just the start of things to see and do here.
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 holiday package as early as possible.
Is it cheaper to book a Cheltenham holiday as a package?
You can enjoy significant savings on your next Cheltenham getaway by booking a tailored holiday 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 holiday 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 holiday.
How to plan a trip to Cheltenham?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to visit Cheltenham.
  2. Work out your budget: Ensure you have enough money to cover everything from dining out and transportation to airfares and activities. Your hotel will probably be the largest expense during your trip to Cheltenham.
  3. Set the duration of your trip: Start by listing all the attractions you want to experience in Cheltenham. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your accommodation and airfare: After you've settled on your travel dates and duration, book the right Cheltenham holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.