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.
Grenadine House

Grenadine House

$627
per person
Nov 8 - Nov 13
found 24 hours ago
Roundtrip flight included
Bridgetown (BGI) to Argyle (SVD)
9.2/10 Wonderful! (395 reviews)
Young Island Resort

Young Island Resort

Save 100% on your flight
$1,043
per person
Nov 8 - Nov 13
found 24 hours ago
Roundtrip flight included
Bridgetown (BGI) to Argyle (SVD)
8.8/10 Excellent! (73 reviews)
Amazing place.

Reviewed on Aug 13, 2026

LA Vue Boutique Hotel & Beach Club

LA Vue Boutique Hotel & Beach Club

$1,002
per person
Nov 1 - Nov 7
found 24 hours ago
Roundtrip flight included
Bridgetown (BGI) to Argyle (SVD)
8.2/10 Very Good! (117 reviews)
The Liming Bequia

The Liming Bequia

Save 100% on your flight
$1,219
per person
Nov 8 - Nov 13
found 24 hours ago
Roundtrip flight included
Bridgetown (BGI) to Argyle (SVD)
9.6/10 Exceptional! (121 reviews)
Bequia Beach Hotel Luxury Resort & Spa

Bequia Beach Hotel Luxury Resort & Spa

Save 100% on your flight
$1,256
per person
Nov 8 - Nov 13
found 24 hours ago
Roundtrip flight included
Bridgetown (BGI) to Argyle (SVD)
9.8/10 Exceptional! (154 reviews)
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Reviewed on Jul 27, 2026

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Cheltenham Hotel Deals

Sunset Shores Beach Hotel

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

Sunset Shores Beach Hotel
Bequia Plantation Hotel

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

Bequia Plantation Hotel
Beachcombers Hotel

Beachcombers Hotel

Villa beach Villa
$158 nightly
$178 total
Sep 1 - Sep 2
Total with taxes and fees
Beachcombers Hotel
See all 244 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.

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.