Estate Smith Bay Vacations from $1,162

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Your Estate Smith Bay Vacation

Uncover the best of Estate Smith Bay with a tailor-made Estate Smith Bay vacation package. From its coastal scenery and tropical climate to its spectacular views, you'll love discovering this hilly city in the way that you want. Fill your spare time with visits to Magens Bay Beach, Coki Point Beach and Blackbeards Castle, some of the top attractions you should see during a trip to Estate Smith Bay. No matter your travel plans or budget, putting together a tailored Estate Smith Bay vacation is easy with Expedia.

The Latest Estate Smith Bay vacation packages

Price found within the past 48 hours. Click for updated prices.
Secret Harbour Beach Resort

Secret Harbour Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,501, price is now $1,162 per person
$1,162
per person
Nov 14 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to St. Thomas (STT)
8.8/10 Excellent! (1,000 reviews)
Lost electric, no a/c and water for better part of a day, no notice to guests or est. for restoration. Had to pay for water. I was a repeat customer, mentioned at CK in, no recognition, offer for a drink or discount of any sort. Made reservation for dinner, was kept waiting for 50 minutes while others from the bar went ahead. No hotel pick up and delivery to airport. Overall very nice location, average staff, dated facilities .

Reviewed on Aug 18, 2025

Club Wyndham Elysian Beach Resort

Club Wyndham Elysian Beach Resort

3.5 out of 5
Price was $2,442, price is now $1,803 per person
$1,803
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to St. Thomas (STT)
7.8/10 Good! (163 reviews)
Clean room. Staff are very slow if you need towels or a refill on shampoo or body wash or staff just doesn’t answer when you call the desk

Reviewed on Sep 3, 2025

Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
Price was $2,320, price is now $1,715 per person
$1,715
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to St. Thomas (STT)
8/10 Very Good! (2,231 reviews)
Great rooftop pool!

Reviewed on Sep 3, 2025

Calichi at Picture Point

Calichi at Picture Point

4 out of 5
Price was $4,123, price is now $3,180 per person
$3,180
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to St. Thomas (STT)
9.8/10 Exceptional! (72 reviews)
Absolutely incredible! Stunning, breathtaking views! Tiffany was great with communication. Most perfect spot for our 10 year anniversary! Quiet, peaceful, secluded mountain top resort. 10/10 recommend!

Reviewed on Aug 23, 2025

Wharfside Village Hotel

Wharfside Village Hotel

3 out of 5
Save 100% on your flight
Price was $1,964, price is now $1,528 per person
$1,528
per person
Oct 25 - Oct 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to St. Thomas (STT)
9.8/10 Exceptional! (127 reviews)
This property is situated in the heart of the town. We felt very welcome and just like family. Overlooking the ocean was another big plus. You’re just steps away from the white sands of St. John and arm length away from amazing people and culture. Hy stay anywhere else.

Reviewed on Aug 6, 2025

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Discover the most popular places to visit in Estate Smith Bay

Wyndham Sugar Bay Beach

Why not spend a lazy afternoon at Wyndham Sugar Bay Beach during your trip to Frydendal? Amble around this romantic area's beautiful beaches, or seek out the snorkeling spots.

Wyndham Sugar Bay Beach

What to do in Estate Smith Bay

Champagne Sunset Sail from Margaritaville Resort

Champagne Sunset Sail from Margaritaville Resort

$124
per adult
100% of travellers recommend
Champagne Sunset Sail from Margaritaville Resort
National Park Snorkeling Excursion

National Park Snorkeling Excursion

$90
per adult
100% of travellers recommend
National Park Snorkeling Excursion
Cocktail Sunset Cruise aboard Breakaway Charters at Sapphire

Cocktail Sunset Cruise aboard Breakaway Charters at Sapphire

$117
per adult
90% of travellers recommend
Cocktail Sunset Cruise aboard Breakaway Charters at Sapphire
See all activities in Estate Smith Bay

Estate Smith Bay Hotel Deals

View of Paradise at Sapphire Beach

View of Paradise at Sapphire Beach

3.5 out of 5
6720 Estate Smith Bay, St. Thomas
$435 nightly
The price is $490 total per night from Sep 8 to Sep 9
$490 total
Sep 8 - Sep 9
Total with taxes and fees
View of Paradise at Sapphire Beach
Sapphire Beach Resort

Sapphire Beach Resort

3 out of 5
6720 Estate Smith Bay, St. Thomas
Get rates
Sapphire Beach Resort
Point Pleasant Resort

Point Pleasant Resort

4 out of 5
6600 Estate Smith Bay, St. Thomas, St. Thomas
Get rates
Point Pleasant Resort
See all 478 properties in Estate Smith 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.

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Frequently asked questions

How much does an Estate Smith Bay vacation package cost?
You can pick up a vacation package to this destination from $1,162 on Expedia. However, how much your vacation to Estate Smith Bay costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Estate Smith Bay?
If you're hoping to snag a cheap Estate Smith Bay vacation package, consider traveling in August, September and December. You'll typically find better prices on accommodations and flights during these months — ideal for travelers wishing to save money.
How many days is enough for Estate Smith Bay?
Usually, a handful of days is enough to visit the major attractions during your Estate Smith Bay vacation. However, if you'd like to have time to unwind or take day trips, consider extending your itinerary.
How to find the best Estate Smith Bay package deals?
Use Expedia's handy filters to find some terrific Estate Smith Bay package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Estate Smith Bay package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book an Estate Smith Bay vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component separately. And you'll still have the freedom to create a personalized Estate Smith Bay vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Estate Smith Bay?
Score incredible discounts by reserving your flights in advance with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Estate Smith Bay adventure.
How to plan a trip to Estate Smith Bay?

  1. Choose when to travel: Check your schedule and get your bags packed. Your favorite time of year and the activities available will also help you decide when to escape to Estate Smith Bay.
  2. Budget wisely: As well as the price of your hotel, you should consider other expenses. These include flights, food and transportation. Also, set aside some extra funds for unexpected costs that may come up during your trip to Estate Smith Bay.
  3. Organize your Estate Smith Bay getaway with our trip planning tool: Search for and book accommodations and activities all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Estate Smith Bay together.
  4. Decide how long to go away for: Now that you're more familiar with Estate Smith Bay, you can work out the right length of your break. Pull together a draft itinerary and allocate enough time to cover everything you want to see.
  5. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a personalized Estate Smith Bay vacation package.
  6. Book activities and experiences ahead of time: Whether it's a ticket to a major attraction or a walking tour, you won't have to worry about missing out on Estate Smith Bay's highlights. Find all the incredible things to do in Estate Smith Bay with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Estate Smith Bay vacation packages?
Set off on your perfect escape to Estate Smith Bay with our Book Now, Pay Later vacations. No need to save like crazy or wait until your next payday — we've teamed up with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans let you spread the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stick to your budget and snap up bargains while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.