Cheltenham Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Things to do in and around Cheltenham

Cheltenham offers a delightful mix of outdoor adventures and cultural experiences, making it perfect for a scenic getaway. Enjoy leisurely strolls through its charming streets, explore the vibrant shopping centres, and partake in the renowned Cheltenham festivals. Additionally, you can unwind at the Everyman Theatre or opt for a unique stay in one of the camping pods, all while indulging in the local golf scene and various attractions.

Shopping

For shopping in Cheltenham, visit Gloucester Quays, an 12.9km away shopping centre offering a vibrant mix of shops and entertainment. If you're up for a drive, explore the Highgrove Shop in Tetbury, located 30.6km away, for unique gifts and souvenirs.

Recreation

At the Everyman Theatre, immerse yourself in captivating performances that blend romance and culture, creating a unique entertainment experience. For outdoor enthusiasts, Cleeve Hill Golf Club offers stunning views and invigorating rounds of golf, perfect for relaxation and recreation amidst nature's beauty.

Adventure

Experience the thrill of Prescott Speed Hill Climb, where motor racing enthusiasts can watch exciting events in a vibrant atmosphere. For a family-friendly adventure, navigate the twists and turns of the Dragonfly Maze, and if you're keen on skiing, the Gloucester Ski and Snowboard Centre offers exhilarating slopes 12.9km away.

Nightlife

Cheltenham's nightlife offers vibrant pubs like The Swan, perfect for a lively evening, and the chic 131 Lounge for cocktails. For live music, check out The Frog and Fiddle, while The Alchemist provides a unique dining experience with creative cocktails to round off your night.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Cheltenham

Cheltenham, renowned for its picturesque scenery and outdoor adventures, boasts a variety of attractions including historic houses, charming churches, and urban parks. This delightful town caters to culture enthusiasts, families, and those seeking outdoor experiences. A visit during the Cheltenham Festival adds an extra layer of excitement to your stay, making it an ideal destination for travellers looking to immerse themselves in local heritage and vibrant community events.

  • Sudeley Castle: Nestled in the picturesque Cotswolds, Sudeley Castle boasts stunning gardens and rich history, offering a romantic atmosphere. Explore its beautifully restored interiors and discover tales of royalty, including its association with Queen Katherine Parr, the last wife of Henry VIII. The surrounding grounds are perfect for leisurely strolls amidst scenic views.
  • Pitville Pump Room: This magnificent Regency building serves as a hub for events and conferences, exuding elegance and sophistication. Originally built as a spa, it features stunning architecture and beautiful gardens, making it an ideal venue for social gatherings while offering a glimpse into Cheltenham’s rich spa history.
  • Cheltenham Art Gallery and Museum: A cultural gem, this gallery houses an impressive collection of art and historical artefacts. Visitors can immerse themselves in exhibitions showcasing both local and international artists, providing a vibrant insight into the region's artistic heritage.

Best time to go to Cheltenham

The best time to visit Cheltenham can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Cheltenham falls in July, when visitor numbers are average and weather is mostly cloudy with light rain. The coolest average temperature in Cheltenham falls in January, visitor numbers are average and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January39.4°F (4.1°C)Light RainMostly CloudyAverageSlightly Low
February40.5°F (4.7°C)Light RainMostly CloudyModerately HighSlightly Low
March43.2°F (6.2°C)Light RainMostly CloudyModerately HighAverage
April47.1°F (8.4°C)No RainMostly CloudyModerately HighAverage
May52.7°F (11.5°C)Light RainMostly CloudyModerately LowAverage
June58.3°F (14.6°C)Light RainMostly CloudyAverageSlightly High
July61.9°F (16.6°C)Light RainMostly CloudyAverageSlightly High
August61.2°F (16.2°C)Light RainMostly CloudyAverageAverage
September57.4°F (14.1°C)Light RainMostly CloudyAverageSlightly High
October52.0°F (11.1°C)Light RainMostly CloudyModerately LowAverage
November45.3°F (7.4°C)Light RainMostly CloudyAverageAverage
December41.5°F (5.3°C)Light RainMostly CloudyModerately LowSlightly Low

Tips to save on your trip to Cheltenham

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Cheltenham during the low season (December to February) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Top hotels in Cheltenham

Cheltenham Chase Hotel & Spa

Cheltenham Chase Hotel & Spa

Shurdington Road Cheltenham England
Fully refundableReserve now, pay when you stay
S$120
15 Oct - 16 Oct
includes taxes & fees
8.2/10 Very good! (1,001 reviews)
"Well ! This was our third stay at Cheltenham chase and things have changed. Firstly at booking in had to wait for 40 minutes to get our room, all superior rooms were ready on time, but not ours. Found a dirty bath towel in a drawer and the bed sheet had a rip in it ! Expected better service better ..."

Reviewed on 12 Sept, 2026

Cheltenham Chase Hotel & Spa
Queens Hotel Cheltenham

Queens Hotel Cheltenham

The Promenade Cheltenham England
Fully refundableReserve now, pay when you stay
S$174
27 Sept - 28 Sept
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"One of the nicest places I have stayed in, exceptionally clean, perfect location, comfy and as a birthday treat, pure excellence. Thank you for making our weekend perfect."

Reviewed on 13 Sept, 2026

Queens Hotel Cheltenham
Leonardo Hotel Cheltenham

Leonardo Hotel Cheltenham

Gloucester Road Cheltenham England
Fully refundableReserve now, pay when you stay
S$131
4 Oct - 5 Oct
includes taxes & fees
8.4/10 Very good! (1,000 reviews)
"Breakfast and helpful receptionist very good. I booked this hotel as it had an EV charger. Our neighbours in the room nextdoor were a bit noisy, but no fault of the hotel. The duvets were too warm for a summer's day, and only read the bit about asking for a sheet too late."

Reviewed on 11 Sept, 2026

Leonardo Hotel Cheltenham
See all 1,285 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.

Stay near popular Cheltenham attractions

A rural landscape with a large open field, a small village, and distant hills.

Cheltenham Racecourse

9.0/10 (199 reviews)
Experience the pinnacle of British horse racing at this historic venue, home to the prestigious Cheltenham Festival. Watch champion thoroughbreds compete while enjoying upscale hospitality.
See properties
An ancient stone structure surrounded by lush greenery and purple flowers.

Sudeley Castle

9.0/10 (101 reviews)
Explore the 1,000-year-old royal castle, final resting place of Queen Katherine Parr, Henry VIII's last wife. Wander through ten award-winning gardens with over 80 rose varieties set against the Cotswold Hills.
See properties
A park with picnic tables, a stone wall, and a building in the background.

Chedworth Roman Villa

8.6/10 (32 reviews)
This elaborate Roman villa showcases Britain's ancient luxury with intricate mosaics and hypocaust heating systems. Walk the elevated pathways for close-up views of remarkable floor artistry preserved from antiquity.
See properties
A stone building with multiple chimneys, surrounded by a well-maintained garden with flowers and a stone wall.

The Model Village

8.6/10 (39 reviews)
Step into a one-ninth scale replica of Bourton-on-the-Water, meticulously crafted from local Cotswold stone. Peek through tiny church windows to glimpse carved pews as choir music plays in this charming miniature world.
See properties
A stone bridge over a canal with a reflection in the water, surrounded by trees and blooming pink flowers.
Photo by Brian Flanagan

Pittville Park

9.0/10 (48 reviews)
Cheltenham's largest ornamental park showcases a Grade I listed Pump Room and tranquil lakes dating to 1825. Enjoy boating, tennis, or simply wander through manicured gardens before relaxing at the lakeside café.
See properties

Cotswold Countryside Collection

9.0/10 (45 reviews)
This collection showcases the quintessential English countryside with honey-colored stone villages and rolling hills. Explore charming tea rooms, historic manor houses, and winding footpaths through idyllic landscapes.
See properties

Cotswold Farm Park

8.8/10 (34 reviews)
At Adam Henson's Cotswold Farm Park, rare British breeds find sanctuary. Feed Highland cattle, cuddle lambs, or watch farming demonstrations in this hands-on countryside experience.
See properties

Prescott Speed Hill Climb

7.8/10 (6 reviews)
Set in the Cotswold countryside, Prescott Speed Hill Climb thrills motorsport enthusiasts with its challenging 1,127-yard track. Visitors can mingle with drivers and witness vintage cars tackle the famous hairpin bend.
See properties

What to do in Cheltenham

Oxford and Traditional Cotswolds Villages from London

Oxford and Traditional Cotswolds Villages from London

S$171
per adult
100% of travellers recommend
Oxford and Traditional Cotswolds Villages from London
Cotswolds in a Day Tour from Moreton-in-Marsh / Stratford-on-Avon

Cotswolds in a Day Tour from Moreton-in-Marsh / Stratford-on-Avon

S$164
per adult
98% of travellers recommend
Cotswolds in a Day Tour from Moreton-in-Marsh / Stratford-on-Avon
Cotswolds: One Day Cotswolds Walking Tour

Cotswolds: One Day Cotswolds Walking Tour

S$155
per adult
Cotswolds: One Day Cotswolds Walking Tour
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.

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. 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.