Estate Trunk Bay Vacations from $753

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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.

The Latest Estate Trunk Bay vacation packages

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

Windward Passage Hotel

3.5 out of 5
Price was $1,227, price is now $753 per person
$753
per person
Dec 14 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to St. Thomas (STT)
7/10 Good! (1,364 reviews)
Perfect for overnight stays

Reviewed on Oct 29, 2025

The Saint Resort

The Saint Resort

3 out of 5
Price was $2,982, price is now $1,551 per person
$1,551
per person
Jan 16 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to St. Thomas (STT)
9.8/10 Exceptional! (19 reviews)
Everything was fantastic

Reviewed on Oct 17, 2025

Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
Price was $1,578, price is now $1,000 per person
$1,000
per person
Dec 14 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to St. Thomas (STT)
8/10 Very Good! (2,281 reviews)
It was a very clean and nice staff would definitely be back!!!

Reviewed on Nov 3, 2025

Wharfside Village Hotel

Wharfside Village Hotel

3 out of 5
Save 100% on your flight
Price was $2,093, price is now $1,410 per person
$1,410
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to St. Thomas (STT)
9.8/10 Exceptional! (131 reviews)
Great Location and outstanding service all around by Hotel staff !

Reviewed on Oct 30, 2025

The Westin St. Thomas Beach Resort & Spa

The Westin St. Thomas Beach Resort & Spa

4.5 out of 5
Price was $1,701, price is now $1,171 per person
$1,171
per person
Dec 14 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to St. Thomas (STT)
8.4/10 Very Good! (1,014 reviews)
Clean room, but we had problems with the shower. Also expect to spend a lot of money for food in the restaurant also they charge $35 for parking per day better to go eat someplace in town a lot cheaper and food is a lot better beach is beautiful and extremely warm water

Reviewed on Oct 29, 2025

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Estate Trunk Bay Hotel Deals

The Westin St. Thomas Beach Resort & Spa

The Westin St. Thomas Beach Resort & Spa

4.5 out of 5
5 Estate Bakkeroe, Po Box 7100, St. Thomas, St. Thomas
$447 nightly
The price is $501 total per night from Dec 3 to Dec 4
$501 total
Dec 3 - Dec 4
Total with taxes and fees
8.2/10 Very Good! (1,003 reviews)
Clean room, but we had problems with the shower. Also expect to spend a lot of money for food in the restaurant also they charge $35 for parking per day better to go eat someplace in town a lot cheaper and food is a lot better beach is beautiful and extremely warm water

Reviewed on Oct 29, 2025

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
$341 nightly
The price is $384 total per night from Nov 4 to Nov 5
$384 total
Nov 4 - Nov 5
Total with taxes and fees
8/10 Very Good! (2,292 reviews)
The rooms were very clean, comfy beds had all the amenities you need. The staff were friendly also especially whom we gave nicknames to is "Versace " and cousin " Neil " the transporter guys,they were awesome .

Reviewed on Nov 2, 2025

Margaritaville Vacation Club - St. Thomas
Windward Passage Hotel

Windward Passage Hotel

3.5 out of 5
Veterans Drive Charlotte Amali, Po Box 640, St. Thomas, St. Thomas
Fully refundableReserve now, pay when you stay
$193 nightly
The price is $215 total per night from Nov 4 to Nov 5
$215 total
Nov 4 - Nov 5
Total with taxes and fees
7/10 Good! (1,358 reviews)
Ok

Reviewed on Oct 27, 2025

Windward Passage Hotel
See all 3,708 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.

Find the Best Estate Trunk Bay Vacation Packages

Estate Trunk Bay Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Cyril E. King Airport (STT)
Top Sights
Trunk Bay, Honeymoon Beach and Maho Beach

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Frequently asked questions

How much does an Estate Trunk Bay vacation package cost?
Offering excellent value package deals from $753 on Expedia, you'll be pleasantly surprised at how much a vacation to Estate Trunk Bay costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Estate Trunk Bay?
You're likely to find lower prices and greater availability in August, September and October. Explore our cheap Estate Trunk Bay vacation packages and you could get some great off-season deals.
How many days is enough for Estate Trunk Bay?
Usually, a handful of days is enough to explore the top sights during your Estate Trunk Bay vacation. However, if you'd like to have some time to kick back or go on day trips, think about extending your itinerary.
How to find the best Estate Trunk Bay package deals?
Bagging a cheap Estate Trunk Bay package deal is a cinch with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget range, add a couple of filters and see what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most affordable Estate Trunk Bay package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book an Estate Trunk Bay vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component individually. And you'll still get the flexibility to create a tailored Estate Trunk Bay vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Estate Trunk Bay?
If you're considering a spur-of-the-moment Estate Trunk Bay vacation, check out 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 hotels and flights by booking ahead.
How to plan a trip to Estate Trunk Bay?

  1. Choose when to get away: Check your diary and get your bags packed. Your preferred time of year and the type of activities available will also help you decide when to visit Estate Trunk Bay.
  2. Budget wisely: Besides the cost of your hotel, you should factor in other expenses. These include flights, transportation and food. Also, put aside a little extra for unexpected costs that could crop up during your trip to Estate Trunk Bay.
  3. Organize your Estate Trunk Bay getaway with our trip planning tool: Search for and book stays and activities all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Estate Trunk Bay together.
  4. Decide how long to go for: Now that you're up to speed on Estate Trunk Bay, you can work out the right length of your vacation. Pull together a draft itinerary and give yourself enough time to cover everything you want to see.
  5. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to pick an Estate Trunk Bay vacation package that brings all your bookings together.
  6. Add on experiences and excursions: Have a look at our travel guide to find some exciting things to do in Estate Trunk Bay. Book tickets or make reservations as soon as you can to save time and avoid the hassle of searching for activities when you arrive.

Does Expedia offer Book Now, Pay Later Estate Trunk Bay vacation packages?
Jet off on your perfect trip to Estate Trunk Bay with help from Expedia's Book Now, Pay Later vacations. No need to save up or wait for the next payday — we've joined forces with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily stay on budget and snap up bargains before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.