Estate Trunk Bay Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Eric Sturgeon

  • 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 Estate Trunk Bay Vacation

The best way to experience this vibrant city is with a tailor-made Estate Trunk Bay vacation package. Base yourself in the neighborhood of Belle Vue, which is good for views, underwater activities and watersports or go someplace else — our packages are all about you. If sightseeing is on the agenda during your trip to Estate Trunk Bay, check out leading attractions like Trunk Bay, Annaberg Plantation and Cinnamon Bay Beach. Don't delay exploring this city any longer. Your perfect Estate Trunk Bay vacation is a few clicks away with Expedia.

Top Estate Trunk Bay Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Breeze

The Breeze

2 out of 5
Price was CA $1,918, price is now CA $1,590 per person
CA $1,590
per person
Jan 23 - Jan 30
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
No reviews

Windward Passage Hotel

Windward Passage Hotel

3.5 out of 5
Price was CA $2,225, price is now CA $1,682 per person
CA $1,682
per person
Jan 23 - Jan 30
just found
Roundtrip non-stop flight included
Toronto (YYZ) to St. Thomas (STT)
7.2/10 Good! (1,495 reviews)
La estadia fue excepcional y a pesar que no tenian luz, el generador estuvo todo el tiempo funcionando a toda capacidad incluyendo ascensores. El hotel queda cerca de bares, restaurantes y el aeropuerto, para mi proxima vez no dudaria en volverme a quedar en Windward Passage Hotel St.Thomas. Gracias

Reviewed on Oct 30, 2026

Calichi at Picture Point

Calichi at Picture Point

4 out of 5
Price was CA $5,764, price is now CA $4,783 per person
CA $4,783
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Thomas (STT)
9.8/10 Exceptional! (86 reviews)
Amazing view!!! rooftop hot tub at Papaya was awesome!! Pool and amenities are great!! Keep in mind lots of steps to get to the pool and power grid going out can happen but aside from that it was a dream!! Will definitely come back someday!!

Reviewed on Oct 23, 2026

The Mary Anne Boutique Hotel USVI

The Mary Anne Boutique Hotel USVI

2.5 out of 5
Price was CA $3,412, price is now CA $2,855 per person
CA $2,855
per person
Jan 2 - Jan 8
found 1 hour ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Thomas (STT)
10/10 Exceptional! (30 reviews)
So friendly.. GREAT location (really close to town) If you are looking for an alternative to the big resorts, this is it.

Reviewed on Sep 13, 2026

Sapphire Beach Villa

Sapphire Beach Villa

3.5 out of 5
Price was CA $2,022, price is now CA $1,694 per person
CA $1,694
per person
Jan 13 - Jan 19
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
9.4/10 Exceptional! (89 reviews)
It was a really nice property.

Reviewed on Oct 6, 2026

Ready to book your vacation to Estate Trunk Bay?

 

Choose your dates

Estate Trunk Bay Hotel Deals

Bluebeard's Castle Resort

Bluebeard's Castle Resort

4 out of 5
1331 Estate Taarneberg Charlotte Amalie Saint Thomas
The price is CA $248 per night from Dec 1 to Dec 2
CA $248
CA $306 total
Dec 1 - Dec 2
includes taxes & fees
Bluebeard's Castle Resort
The Westin St. Thomas Beach Resort & Spa

The Westin St. Thomas Beach Resort & Spa

4.5 out of 5
5 Estate Bakkeroe St. Thomas St. Thomas
The price is CA $536 per night from Nov 29 to Nov 30
CA $536
CA $723 total
Nov 29 - Nov 30
includes taxes & fees
8.6/10 Excellent! (1,562 reviews)
"We had a great time at the Westin St. Thomas. The multiple pools, pool and seaside dining options, and the breathtaking views were everything we had hoped for. We had a great stay and will be back!"

Reviewed on Nov 1, 2026

The Westin St. Thomas Beach Resort & Spa
Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
6080 Estate Smith Bay St. Thomas
8/10 Very good! (2,451 reviews)
"I actually enjoyed it. The only thing I did like was a little sewage smell but, ot wasn't every day"

Reviewed on Oct 31, 2026

Get rates
Margaritaville Vacation Club - St. Thomas
See all 4,025 properties in Estate Trunk 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

What to do in Estate Trunk Bay

Champagne Sunset Sail from Margaritaville

Champagne Sunset Sail from Margaritaville

CA $156
per adult
94% of travellers recommend
Champagne Sunset Sail from Margaritaville
Henley Cay Adventure Tour in St John

Best of St. John: Kayak, Snorkel with Sea Turtles & Picnic

CA $241
per adult
Best of St. John: Kayak, Snorkel with Sea Turtles & Picnic
Beach umbrellas on Coki Point Beach in the Virgin Islands.

Coki Beach with Round-Trip Transport

CA $89
per traveller
74% of travellers recommend
Coki Beach with Round-Trip Transport
See all activities in Estate Trunk Bay

Frequently asked questions

How much does an Estate Trunk Bay vacation package cost?
Get set to book, because a getaway to Estate Trunk Bay starts from just CA $1,590. When you bundle your hotels, flights and car rentals into a package, you'll land the best deals.
How do I get a cheap travel package to Estate Trunk Bay?
One of the simplest ways to save cash (and time) is to bundle your bookings with Expedia. Hotels, rental cars, flights and activities — we've got them all. Choose a combination that suits your style and watch your savings pile up. We know a package deal is never a one-size-fits-all. That's why Expedia offers over 550 partner airlines and 1,000,000 hotel options across the globe, which lets you customize your Estate Trunk Bay vacation.
Where should I stay in Estate Trunk Bay?
With loads to explore in Estate Trunk Bay, it's a good idea to book a hotel near its attractions. Trunk Bay, Annaberg Plantation and Cinnamon Bay Beach are some good ones to add to your must-see list.
How far in advance should I book my Estate Trunk Bay vacation?
It can be hard to know when is the perfect time to book your trip to Estate Trunk Bay. But generally the earlier you book, the lower the prices. In some cases, you can lock in your flights and hotels nearly a year before your departure date. If you're hoping for a last-minute getaway, no need to worry! There are great bargains announced on Expedia every day.
What does an Expedia Estate Trunk Bay travel package include?
That depends entirely on you. You can pick from a variety of Estate Trunk Bay packages, such as a hotel, flight and rental car. You can also book a hotel and a flight, or a flight and a rental car. Once you've made your booking, you can add the fun stuff like activities and experiences. Whatever your ideal Estate Trunk Bay trip looks like, get ready to save!
What should I know before booking an Estate Trunk Bay travel package?
You can look forward to saving with an Expedia travel package. Combine your flights, rental cars and hotels and land terrific discounts. Hotels aren't your only choice, though. We have beachfront villas, cozy city apartments and even glamping tents!
Can I choose my airline with an Estate Trunk Bay Expedia vacation package?
Yes, and with more than 550 airlines to choose from worldwide, you're spoiled for choice. Browse the available options and see which airline fits your budget and needs.
If I'm not able to travel, can I cancel my Estate Trunk Bay vacation package?
If your vacation plans in Estate Trunk Bay have changed, it's good to know that you can cancel or amend your booking. If you made your booking less than 24 hours ago, you may be able to get a refund. If your booking is older than that, your airline, hotel or car rental company may charge fees. To find out more, visit our Customer Service Portal.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.