Cruz Bay Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 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

Top Cruz Bay Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel 1829

Hotel 1829

3.5 out of 5
Price was CA $2,271, price is now CA $1,744 per person
CA $1,744
per person
May 13 - May 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
9.8/10 Exceptional! (7 reviews)
We loved our room and the shower was awesome!! The hotel and bar staff were fantastic!! We spent a peaceful afternoon in the hotel pool. Wonderful getaway!!

Reviewed on Feb 27, 2026

Wharfside Village Hotel

Wharfside Village Hotel

3 out of 5
Price was CA $4,282, price is now CA $3,122 per person
CA $3,122
per person
May 5 - May 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
9.8/10 Exceptional! (133 reviews)
Staff was welcoming, assisted with luggage, room was immaculate and public areas were very clean as well.

Reviewed on Mar 1, 2026

Calichi at Picture Point

Calichi at Picture Point

4 out of 5
Price was CA $6,000, price is now CA $4,561 per person
CA $4,561
per person
Apr 25 - May 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Thomas (STT)
9.8/10 Exceptional! (73 reviews)
Gorgeous property. Amazing views. Well furnished. Great communication. Property management went out of their way for the little extras to make it a most memorable experience.

Reviewed on Feb 26, 2026

Great Bay Condominiums located at The Ritz-Carlton Club, St Thomas

Great Bay Condominiums located at The Ritz-Carlton Club, St Thomas

4.5 out of 5
Price was CA $6,445, price is now CA $4,925 per person
CA $4,925
per person
Apr 18 - Apr 25
found 9 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Thomas (STT)
9.2/10 Wonderful! (33 reviews)
Villa Island Paradise

Villa Island Paradise

4 out of 5
Price was CA $3,309, price is now CA $2,637 per person
CA $2,637
per person
May 5 - May 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
9/10 Wonderful! (2 reviews)
Everything was clean and well appointed.

Reviewed on Mar 1, 2026

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now

Cruz Bay Hotel Deals

The Westin St. John Resort Villas

The Westin St. John Resort Villas

4.5 out of 5
300B Chocolate Hole St. John
The price is CA $994 per night from Mar 4 to Mar 5
CA $994
CA $1,119 total
Mar 4 - Mar 5
includes taxes & fees
8.2/10 Very Good! (465 reviews)
Great

Reviewed on Feb 20, 2026

The Westin St. John Resort Villas
Villa Island Paradise

Villa Island Paradise

4 out of 5
St John St. John St John
The price is CA $131 per night from Mar 8 to Mar 9
CA $131
CA $873 total
Mar 8 - Mar 9
includes taxes & fees
9.4/10 Exceptional! (17 reviews)
Everything was clean and well appointed.

Reviewed on Mar 1, 2026

Villa Island Paradise
St John Inn

St John Inn

3 out of 5
277 Estate Enighed St. John
The price is CA $483 per night from Mar 9 to Mar 10
CA $483
CA $544 total
Mar 9 - Mar 10
includes taxes & fees
9.2/10 Wonderful! (425 reviews)
The attention to details stood out. Just a wonderful time and I will return!!! ♥️

Reviewed on Feb 18, 2026

St John Inn
See all 1,064 properties in Cruz Bay
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 Cruz Bay vacation package cost?
Our Cruz Bay vacation packages, which start at just CA $1,744, are an ideal way to save big. Select your preferred flights, hotels and rental cars to create your dream itinerary.
How do I get a cheap travel package to Cruz Bay?
One of the easiest ways to save money (and time) is to bundle your bookings with Expedia. Flights, rental cars, hotels and activities — we've got it all. Select a combination that best fits you and watch your savings stack up. Of course, a package deal is never one-size-fits-all. That's why Expedia offers over 550 airlines and 1,000,000 hotel options around the globe, which lets you customize your Cruz Bay vacation.
Where should I stay in Cruz Bay?
We recommend staying near the action. Many visitors book hotels around popular attractions, like Trunk Bay, Cinnamon Bay Beach and Honeymoon Beach.
What are the top hotels in Cruz Bay?
Secure a room at Gallows Point 8d, Luxury Oceanview Upper Premium Condo At Gallows Point Resort. It's one of this area's most in-demand properties. Another highly rated option in Cruz Bay is Nancy's Folly Villa - Fabulous Home.
How far in advance should I book my Cruz Bay vacation?
Browse Expedia to compare international airfares as soon as you know your travel dates. You can generally purchase a seat up to 12 months in advance. If you can't see your preferred air carrier, or you're booking late, don't stress. Cheap tickets to Cruz Bay occasionally appear just weeks before the date of departure.
What does an Expedia Cruz Bay travel package include?
Expedia has everything you need to organize your Cruz Bay getaway, but what goes into your package is your call. Select from a combination of flights, rental cars and hotels. Searching for some tours or experiences to keep you on the move? Once you've made your booking, you can add them too. Whatever your budget or style, there's a deal to suit your needs.
What should I know before booking a Cruz Bay travel package?
Locking in all the parts of your escape together is a great way to save. Bundle your car rentals, airfares and hotels into a neat little package. But your options don't end at hotels. Expedia has all sorts of properties, including vacation rentals like beach villas and city residences. You've got choices galore!
Can I choose my airline with a Cruz Bay Expedia vacation package?
You certainly can. We offer more than 550 partner airlines globally, so fly with the carrier that fits your budget and traveling style.
If I'm not able to travel, can I cancel my Cruz Bay vacation package?
Your situation can change in the blink of an eye, so yes, you can. You may be able to cancel or alter your Cruz Bay vacation package at no cost within 24 hours of booking. For bookings older than that, you can still cancel or make changes, but your car rental company, hotel or airline may impose a fee. Looking for more information? Have a look at our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.

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.