Cheltenham Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Cheltenham
Sunset Shores Beach Hotel
Windward Highway Villa
S$172
16 Sept - 17 Sept
includes taxes & fees
8.6/10 Excellent! (809 reviews)
"This property gives you the home away from home feeling. The staff treat you as loved ones because they provide care with each interaction. Hands-down, the best food we had on the island of St. Vincent! This hotel was in an excellent proximity to the main town, ferries, other eateries and nightlife. ..."
Reviewed on 1 Sept, 2026
Bequia Plantation Hotel
Belmont Road, Port Elizabeth Harbor Bequia Island
Fully refundableReserve now, pay when you stay
S$342
2 Sept - 3 Sept
includes taxes & fees
9.2/10 Wonderful! (434 reviews)
"I had such a wonderful stay at this property, I was originally supposed to stay for one night but I ended up staying an extra night. The room is comfortable and clean, had a kitchenette which was useful. The hotel is right on the beach, so wake up early for some beautiful peaceful sunrise. There ..."
Reviewed on 1 Sept, 2026
Beachcombers Hotel
Villa beach Villa
S$235
4 Sept - 5 Sept
includes taxes & fees
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.
Frequently asked questions
How much does a Cheltenham holiday package cost?
You can snap up a holiday package to this top destination on Expedia. But how much your holiday to Cheltenham costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Cheltenham?
You can typically find reduced prices and greater availability in August, September and October. Browse our cheap Cheltenham holiday packages and you could score some great off-season deals.
How many days is enough for Cheltenham?
Typically, a handful of days is enough to visit the top sights during your Cheltenham holiday. However, if you'd like to have some time to chill out or go on day tours, consider extending your trip.
How to find the best Cheltenham package deals?
Use Expedia's handy filters to find some terrific Cheltenham package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for Cheltenham package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your holiday package well in advance.
Is it cheaper to book a Cheltenham holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging flights and accommodation separately. Better still, you can customise your Cheltenham trip to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Cheltenham?
Enjoy incredible discounts by booking your flights early with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Cheltenham escape.
How to plan a trip to Cheltenham?
- Choose the ideal time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to go to Cheltenham.
- Calculate your budget: Make sure you have enough money to cover everything from food and transportation to experiences and flights. Your hotel will likely be the biggest expense during your trip to Cheltenham.
- Decide how long to go for: Now that you know more about Cheltenham, you can figure out the ideal length of your holiday. Put together a draft plan and give yourself enough time to cover everything you want to see.
- Bundle your accommodation and airfare: Once you've nailed down your trip 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.
