Cheltenham Holidays

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Cheltenham Holiday

Our pick of the best Cheltenham Hotel Deals

Leonardo Hotel Cheltenham

Leonardo Hotel Cheltenham

4 out of 5
Gloucester Road, Cheltenham, England
Fully refundableReserve now, pay when you stay
The price is NZ$175 per night from 31 Aug to 1 Sept
NZ$175
31 Aug - 1 Sept
includes taxes & fees
8.2/10 Very Good! (1,005 reviews)
"Amazing reception, great gym, perfect breakfast, but no air con and pillow (both available) quite big."

Reviewed on 12 Aug. 2025

Leonardo 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
The price is NZ$175 per night from 4 Sept to 5 Sept
NZ$175
4 Sept - 5 Sept
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
Great hotel
"Great hotel with friendly staff who welcomed me and my friend with a smile. Very quick checking us in as well. Room was spacious and the floor we was on was quiet as well. Overall great experience, will be back again soon !"

Reviewed on 10 Aug. 2025

Cheltenham Chase Hotel & Spa
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 NZ$204 per night from 31 Aug to 1 Sept
NZ$204
31 Aug - 1 Sept
includes taxes & fees
8.8/10 Excellent! (580 reviews)
"Room was beautifully styled, bed and bedding very comforting. Staff were lovely and the free biscuits at reception and in the room were a lovely bonus! One minor issue: sound carried quite loudly from the corridor to my room (though luckily the hotel was quiet so only happened briefly/ a couple of ..."

Reviewed on 12 Aug. 2025

The George
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.

Discover the most popular places to visit in Cheltenham

Sudeley Castle which includes 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
The Model Village showing 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
Chedworth Roman Villa showing heritage elements, a garden and a pond

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

Scenic Transfer from Stratford Upon Avon to London Via Cotswolds

Scenic Transfer from Stratford Upon Avon to London Via Cotswolds

NZ$202
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

NZ$30
per traveller
Classic Cotswolds – Online Self-Guided Road Trip Plan
Bourton-on-the-Water

Private One Day Luxury Tour of The Cotswolds

NZ$2,125
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.