Estate Trunk Bay Vacations from $699

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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
Save 100% on your flight
Price was $1,138, price is now $699 per person
$699
per person
Jan 4 - Jan 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. Thomas (STT)
7/10 Good! (1,366 reviews)
Yes, the room was clean

Reviewed on Dec 1, 2025

Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
Save 100% on your flight
Price was $2,122, price is now $1,179 per person
$1,179
per person
Jan 6 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to St. Thomas (STT)
8/10 Very Good! (2,299 reviews)
Room was nice and bartenders and golf cart driver's were very nice, really all the staff was helpful!!!

Reviewed on Dec 1, 2025

At Home in the Tropics

At Home in the Tropics

3 out of 5
Save 100% on your flight
Price was $1,430, price is now $800 per person
$800
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. Thomas (STT)
9.8/10 Exceptional! (149 reviews)
The property managers made me feel very welcomed and this property stays locked so me and my girlfriend felt very safe the entire trip. Planning on saving more money and will come back to visit asap. Would recommend to anyone and everyone visiting st Thomas

Reviewed on Jul 21, 2025

Villa Island Paradise

Villa Island Paradise

4 out of 5
Price was $5,131, price is now $2,893 per person
$2,893
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. Thomas (STT)
9/10 Wonderful! (2 reviews)
Owners wete anazing and went above and beyond. We had solar power when we had an island wide blackout! Loced this place!

Reviewed on Oct 30, 2025

Bluebeard's Castle Resort

Bluebeard's Castle Resort

4 out of 5
Save 100% on your flight
Price was $1,887, price is now $1,139 per person
$1,139
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. Thomas (STT)
No reviews
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Estate Trunk Bay Hotel Deals

Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
6080 Estate Smith Bay St. Thomas
$314 nightly
The price is $353 total per night from Dec 7 to Dec 8
$353 total
Dec 7 - Dec 8
Total with taxes and fees
7.8/10 Good! (2,317 reviews)
Not a swimmable beach.

Reviewed on Nov 25, 2025

Margaritaville Vacation Club - St. Thomas
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
Fully refundableReserve now, pay when you stay
$605 nightly
The price is $679 total per night from Dec 7 to Dec 8
$679 total
Dec 7 - Dec 8
Total with taxes and fees
8.2/10 Very Good! (1,015 reviews)
The staff was amazing especially the front desk.

Reviewed on Nov 27, 2025

The Westin St. Thomas Beach Resort & Spa
Emerald Beach Resort

Emerald Beach Resort

3.5 out of 5
8070 Lindbergh Bay St. Thomas St. Thomas
Fully refundableReserve now, pay when you stay
$256 nightly
The price is $286 total per night from Dec 6 to Dec 7
$286 total
Dec 6 - Dec 7
Total with taxes and fees
7.6/10 Good! (1,133 reviews)
My King Suit looked and smelled GREAT! I had the French Toast for breakfast and I am FAT AND HAPPY! The staff was amazing and very accommodating. I will be back!

Reviewed on Nov 30, 2025

Emerald Beach Resort
See all 3,705 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 $699 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.