Estate Chocolate Hole and Great Cruz Bay Vacations from $847

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Your Estate Chocolate Hole and Great Cruz Bay Vacation

Say bye-bye to the stress of planning and hello to a Estate Chocolate Hole and Great Cruz Bay vacation package. With your travel details organized before you take off, you can focus on discovering the best of this city, starting with Belle Vue, which is great for views, underwater activities and watersports. If your trip to Estate Chocolate Hole and Great Cruz Bay includes some sightseeing, check out renowned attractions like Trunk Bay, Annaberg Plantation and Cinnamon Bay Beach. No matter your travel plans or budget, organizing a tailored Estate Chocolate Hole and Great Cruz Bay vacation is a breeze with Expedia.

The Latest Estate Chocolate Hole and Great Cruz Bay vacation packages

Price found within the past 48 hours. Click for updated prices.
Pirates Pension at Bluebeard's Castle

Pirates Pension at Bluebeard's Castle

3 out of 5
Price was $1,146, price is now $847 per person
$847
per person
Nov 19 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to St. Thomas (STT)
8.4/10 Very Good! (744 reviews)
The room was updated and really nice. Had an amazing view overlooking the entire waterfront, even saw Havensight and hassle island! The front desk service however, was absolutely horrendous. Speaking from a former front desk supervisor, night staff the ladies were terrible. They might need customer service training.

Reviewed on Aug 29, 2025

The Saint Resort

The Saint Resort

3 out of 5
Save 100% on your flight
Price was $1,522, price is now $1,107 per person
$1,107
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to St. Thomas (STT)
9.8/10 Exceptional! (11 reviews)
Amazing boutique hotel! Perfect for couples—we celebrated our anniversary here and had a spectacular time. Great facilities, excellent location near Cruz Bay, and delicious food at the on-site restaurant. Highly recommended!

Reviewed on Aug 27, 2025

Calichi at Picture Point

Calichi at Picture Point

4 out of 5
Save 100% on your flight
Price was $3,520, price is now $2,625 per person
$2,625
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to St. Thomas (STT)
9.8/10 Exceptional! (71 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

Hotel 1829

Hotel 1829

3.5 out of 5
Save 100% on your flight
Price was $1,365, price is now $1,067 per person
$1,067
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to St. Thomas (STT)
9.6/10 Exceptional! (5 reviews)
Club Wyndham Elysian Beach Resort

Club Wyndham Elysian Beach Resort

3.5 out of 5
Price was $1,126, price is now $881 per person
$881
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to St. Thomas (STT)
7.8/10 Good! (161 reviews)
Really enjoyed my stay close to ferry and all staff was so polite and gave great recommendations to dining and places to visit . Even though hurricane Erin made an appearance the staff was very assuring. I felt safe . All the staff at front desk was great wish I could remember all there names but I do remember Khadijah, I would definitely stay there again !!!!

Reviewed on Aug 21, 2025

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Discover the most popular places to visit in Estate Chocolate Hole and Great Cruz Bay

Chocolate Hole Beach

Why not spend a lazy afternoon at Chocolate Hole Beach during your trip to Monte? While you're in the area, stroll along the beautiful beaches.

Chocolate Hole Beach

What to do in Estate Chocolate Hole and Great Cruz Bay

Baths of Virgin Gorda

Discover The Baths of Virgin Gorda Full Day Adventure - Westin St. John

$329
per adult
Discover The Baths of Virgin Gorda Full Day Adventure - Westin St. John
Sailing Catamaran

St. John Jost Van Dyke & Soggy Dollar Snorkel Sail with Breakfast - Westin

$299
per adult
100% of travellers recommend
St. John Jost Van Dyke & Soggy Dollar Snorkel Sail with Breakfast - Westin
Thrilling St. John Island Power Adventure from Westin

Thrilling St. John Island Power Adventure from Westin

$139
per adult
Thrilling St. John Island Power Adventure from Westin
See all activities in Estate Chocolate Hole and Great Cruz Bay

Estate Chocolate Hole and Great Cruz Bay Hotel Deals

The Westin St. John Resort Villas

The Westin St. John Resort Villas

4.5 out of 5
300B Chocolate Hole, P.O. Box 8310, Great Cruz Bay, St. John
$422 nightly
The price is $475 total per night from Sep 1 to Sep 2
$475 total
Sep 1 - Sep 2
Total with taxes and fees
8.2/10 Very Good! (433 reviews)
"Beautiful and peaceful property. My only issues were the air conditioning wasn't strong enough. But all good"

Reviewed on Aug 16, 2025

The Westin St. John Resort Villas
Stunning Views, Peaceful Location, Large Pool & Minutes from Cruz Bay

Stunning Views, Peaceful Location, Large Pool & Minutes from Cruz Bay

cruz bay
9.6/10 Exceptional! (67 reviews)
"This property is beautiful! We had a few hiccups with a few things but overall a great stay. The properly manage was very responsive on text and the house is well stocked. You definitely need a four wheel drive vehicle here. We had an AWD vehicle for the first few days and had to change (due to the ..."

Reviewed on Aug 24, 2025

Get rates
Stunning Views, Peaceful Location, Large Pool & Minutes from Cruz Bay
Tranquil relaxing & private 5 bedroom villa on pond w kayaks paddle boards +++

Tranquil relaxing & private 5 bedroom villa on pond w kayaks paddle boards +++

Cruz Bay
Get rates
Tranquil relaxing & private 5 bedroom villa on pond w kayaks paddle boards +++
See all 490 properties in Estate Chocolate Hole and Great 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.

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Frequently asked questions

How much does an Estate Chocolate Hole and Great Cruz Bay vacation package cost?
You can grab a vacation package to this popular destination from $847 on Expedia. But how much your vacation to Estate Chocolate Hole and Great Cruz Bay costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Estate Chocolate Hole and Great Cruz Bay?
June, October and December are the best times to look for cheap Estate Chocolate Hole and Great Cruz Bay vacation packages. Opting to travel in quieter months means you can typically find reduced prices on flights and accommodations.
How many days is enough for Estate Chocolate Hole and Great Cruz Bay?
Generally, a handful of days is enough to explore the major sights during your Estate Chocolate Hole and Great Cruz Bay vacation. But if you prefer to have some time to kick back or take day tours, consider extending your trip.
How to find the best Estate Chocolate Hole and Great Cruz Bay package deals?
Use Expedia's filter tool to find some great Estate Chocolate Hole and Great Cruz Bay package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Estate Chocolate Hole and Great Cruz Bay package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book an Estate Chocolate Hole and Great Cruz Bay vacation as a package?
You can enjoy significant savings on your next Estate Chocolate Hole and Great Cruz Bay retreat by booking a customized vacation package. Check the "Package" heading, then enter your destination and travel dates to browse some great flight and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Estate Chocolate Hole and Great Cruz Bay?
Score incredible bargains by booking your flights ahead of time with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for an impromptu Estate Chocolate Hole and Great Cruz Bay escape.
How to plan a trip to Estate Chocolate Hole and Great Cruz Bay?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Estate Chocolate Hole and Great Cruz Bay.
  2. Figure out your budget: Make sure you have enough money to pay for everything from transportation and food to experiences and flights. Your accommodations will likely be the biggest expense during your trip to Estate Chocolate Hole and Great Cruz Bay.
  3. Use our trip planning tool to discover Estate Chocolate Hole and Great Cruz Bay: Research every aspect of your trip to Estate Chocolate Hole and Great Cruz Bay with this handy planner. Invite your family and friends to collaborate on a group getaway, search for hotels or things to do and make bookings.
  4. Set the duration of your trip: Start by listing all the activities and attractions you want to get to in Estate Chocolate Hole and Great Cruz Bay. Then, estimate how long you'll need at each, including any travel time.
  5. Combine your airfare and accommodations: Once you've settled on your trip dates and duration, book the ideal Estate Chocolate Hole and Great Cruz Bay vacation package for you.
  6. Book activities and experiences ahead of time: Whether it's entrance to a big attraction or a day trip, you won't have to worry about missing out on the highlights of Estate Chocolate Hole and Great Cruz Bay. Find all the fun things to do in Estate Chocolate Hole and Great Cruz Bay in Estate Chocolate Hole and Great Cruz Bay with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Estate Chocolate Hole and Great Cruz Bay vacation packages?
If you're like us, you love going away but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Estate Chocolate Hole and Great Cruz Bay vacation over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.