Cheltenham Vacations from $627
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Your Cheltenham Vacation
Our vacation packages to Cheltenham offer countless opportunities to immerse yourself in new sights, sounds and flavors. And with all the details worked out, you'll be free to enjoy your city escape to the fullest. Searching for some sightseeing inspiration for your trip to Cheltenham? Cotton House Beach and Macaroni Beach are two must-visit attractions here. A few clicks is all it takes to create a customized Cheltenham vacation on Expedia.
The Latest Cheltenham vacation packages
Price found within the past 48 hours. Click for updated prices.
Cheltenham Hotel Deals
Sunset Shores Beach Hotel
Windward Highway Villa
$118 nightly
$133 total
Sep 2 - Sep 3
Total with taxes and fees
8.6/10 Excellent! (807 reviews)
"Great service, friendly staff, delicious food and excellent amenities."
Reviewed on Aug 30, 2026
Bequia Plantation Hotel
Belmont Road, Port Elizabeth Harbor Bequia Island
Fully refundableReserve now, pay when you stay
$222 nightly
$249 total
Oct 1 - Oct 2
Total with taxes and fees
9.2/10 Wonderful! (433 reviews)
"Peaceful quite location.Beautiful beach. Excellent staff. I'll be back."
Reviewed on Aug 28, 2026
Beachcombers Hotel
Villa beach Villa
$158 nightly
$178 total
Sep 1 - Sep 2
Total with taxes and 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.
Find the Best Cheltenham Vacation Packages
Cheltenham Essential Information
Language | English |
|---|---|
Currency | East Caribbean dollars |
Closest Airport | Argyle Intl. Airport (SVD) |
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Frequently asked questions
How much does a Cheltenham vacation package cost?
You can snap up a vacation package to this top destination from $627 on Expedia. But how much your vacation to Cheltenham costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Cheltenham?
If you're looking to snag a cheap Cheltenham vacation package, consider planning a trip in September, November and December. You'll generally find lower prices on hotels and airfares during these months — perfect for a budget-friendly break.
How many days is enough for Cheltenham?
With a well-planned itinerary, you can easily visit the main Cheltenham sights in a few days. But if you prefer to discover hidden gems or take day trips, think about booking your Cheltenham vacation for longer.
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 vacation package well in advance.
Is it cheaper to book a Cheltenham vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and accommodations separately. Better still, you can customize 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 vacation 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.
Does Expedia offer Book Now, Pay Later Cheltenham vacation packages?
Your Cheltenham trip should be an escape from your busy life, not a source of money-related stress. So to give you 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 total cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
