Cheltenham Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

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.

Top Cheltenham Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Spring Hotel Bequia

Spring Hotel Bequia

3.5 out of 5
Price was CA $1,676, price is now CA $1,429 per person
CA $1,429
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Argyle (SVD)
8.6/10 Excellent! (73 reviews)
We thoroughly enjoyed are stay! We appreciated the larger room and outdoor sitting area!

Reviewed on Apr 20, 2026

Bequia Plantation Hotel

Bequia Plantation Hotel

3.5 out of 5
Price was CA $2,040, price is now CA $1,635 per person
CA $1,635
per person
Aug 12 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Argyle (SVD)
9.2/10 Wonderful! (401 reviews)
Clean rooms, good food, great staff. We had a lovely stay.

Reviewed on Jul 8, 2026

Blue Lagoon Hotel & Marina

Blue Lagoon Hotel & Marina

4 out of 5
Price was CA $1,876, price is now CA $1,579 per person
CA $1,579
per person
Aug 12 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Argyle (SVD)
8.8/10 Excellent! (515 reviews)
Great place to stay

Reviewed on Jul 2, 2026

LA Vue Boutique Hotel & Beach Club

LA Vue Boutique Hotel & Beach Club

3.5 out of 5
Price was CA $2,109, price is now CA $1,778 per person
CA $1,778
per person
Aug 12 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Argyle (SVD)
8.2/10 Very good! (101 reviews)
Nice property, looks like photos, helpful staff. Very good location for carnival events, and access to beach not much restaurants close by

Reviewed on Jul 8, 2026

Sandals St. Vincent and the Grenadines Couples Only

Sandals St. Vincent and the Grenadines Couples Only

4.5 out of 5
Price was CA $5,428, price is now CA $4,620 per person
CA $4,620
per person
Sep 12 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Argyle (SVD)
9.2/10 Wonderful! (45 reviews)
Everything was amazing from the food, too the super kind staff! Too the fantastic clean beach too the pools as well! Everything was top notch

Reviewed on Jul 8, 2026

Ready to book your vacation to Cheltenham?

 

Choose your dates

Cheltenham Hotel Deals

Sunset Shores Beach Hotel

Sunset Shores Beach Hotel

3 out of 5
Windward Highway Villa
The price is CA $168 per night from Jul 26 to Jul 27
CA $168
CA $215 total
Jul 26 - Jul 27
includes taxes & fees
8.6/10 Excellent! (782 reviews)
"Staff was very friendly welcoming professional."

Reviewed on Jul 1, 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 CA $227 per night from Jul 26 to Jul 27
CA $227
CA $278 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (406 reviews)
"Clean rooms, good food, great staff. We had a lovely stay."

Reviewed on Jul 8, 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
The price is CA $179 per night from Jul 18 to Jul 19
CA $179
CA $220 total
Jul 18 - Jul 19
includes taxes & fees
9.6/10 Exceptional! (151 reviews)
"A unique place in a beautiful setting. A car is required as part of the package"

Reviewed on Jun 22, 2026

Holiday Inn Express & Suites St. Vincent - Grenadines by IHG
See all 241 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Cheltenham vacation package cost?
You'll find cheap prices from CA $1,429 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 travelling in August, September and October. You'll typically find lower rates on hotels and airfares during these quieter months — ideal for a budget-friendly break.
How many days is enough for Cheltenham?
The ideal length for your Cheltenham vacation depends on what you'd like to do. Typically, a few days to a week will give you time to hit all the top attractions and explore some hidden treasures along the way.
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 favourite 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.

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.