Cheltenham Vacations

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  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 when you book a flight and hotel together*

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

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Find the Best Cheltenham Vacation Packages

Cheltenham Hotel Deals

Sunset Shores Beach Hotel

Sunset Shores Beach Hotel

3 out of 5
Windward Highway Villa
The price is SARĀ 401 per night from Jul 31 to Aug 1
SARĀ 401
SARĀ 508 total
31 Jul - 1 Aug
includes taxes & fees
8.6/10 Excellent! (784 reviews)
"Great manager and Staff"

Reviewed on 17 July 2026

Sunset Shores Beach Hotel
Bequia Plantation Hotel

Bequia Plantation Hotel

3.5 out of 5
Belmont Road, Port Elizabeth Harbor Bequia Island
Fully refundableReserve now, pay when you stay
The price is SARĀ 661 per night from Jul 27 to Jul 28
SARĀ 661
SARĀ 810 total
27 Jul - 28 Jul
includes taxes & fees
9.2/10 Wonderful! (411 reviews)
"Very hospitable staff. Great stay"

Reviewed on 16 July 2026

Bequia Plantation Hotel
Holiday Inn Express & Suites St. Vincent - Grenadines by IHG

Holiday Inn Express & Suites St. Vincent - Grenadines by IHG

3 out of 5
Windward Highway Diamond
Fully refundable
The price is SARĀ 421 per night from Aug 11 to Aug 12
SARĀ 421
SARĀ 520 total
11 Aug - 12 Aug
includes taxes & fees
9.6/10 Exceptional! (158 reviews)
"It was comfortable and clean. Staff very friendly"

Reviewed on 17 July 2026

Holiday Inn Express & Suites St. Vincent - Grenadines by IHG
See all 242 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.

Frequently asked questions

How much does a Cheltenham vacation package cost?
You'll find cheap prices on Expedia for your Cheltenham escape. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Cheltenham costs.
What are the cheapest months to go to Cheltenham?
If you'd like to book a cheap Cheltenham vacation package, consider traveling in August, September and October. You'll typically find lower rates on hotels and airfares during these quieter months ā€” ideal for a budget-friendly break.
How to find the best Cheltenham package deals?
Use Expedia's handy filters to find some unbeatable Cheltenham package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Cheltenham package deals in the off-season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
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 hotels and flights individually. Better still, you can tailor your Cheltenham trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Cheltenham?
If you're considering a spontaneous Cheltenham adventure, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Cheltenham?

  1. Choose when to go: Check your calendar and pack your bags. Your favorite time of year and the activities on offer will also help you decide when to visit Cheltenham.
  2. Plan your budget wisely: On top of the price of your stay, you'll need to consider other expenses too. These include flights, food and transportation. Also, put aside a little extra for unexpected costs that may crop up during your trip to Cheltenham.
  3. Work out your trip length: Consider how much time you'd like to spend discovering Cheltenham. Plan your days so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a personalized Cheltenham vacation package.