Estate Chocolate Hole and Great Cruz Bay Vacation Packages

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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.

Top Estate Chocolate Hole and Great Cruz Bay Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Limetree Beach Resort by Club Wyndham

Limetree Beach Resort by Club Wyndham

3.5 out of 5
Price was CA $3,054, price is now CA $2,323 per person
CA $2,323
per person
Dec 14 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Thomas (STT)
8.2/10 Very good! (247 reviews)
The studio was clean, the staff was always available when needed, the swim-up bar fabulous and the bar was excellent and the alcohol drinks outstanding.

Reviewed on Oct 30, 2026

The Saint Resort

The Saint Resort

3 out of 5
Price was CA $5,543, price is now CA $4,291 per person
CA $4,291
per person
Dec 21 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Thomas (STT)
9.2/10 Wonderful! (52 reviews)
Good location. Pool was nice.

Reviewed on Nov 2, 2026

Calichi at Picture Point

Calichi at Picture Point

4 out of 5
Save 100% on your flight
Price was CA $5,503, price is now CA $4,315 per person
CA $4,315
per person
Dec 10 - Dec 17
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) 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

Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
Price was CA $3,920, price is now CA $3,143 per person
CA $3,143
per person
Jan 18 - Jan 25
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to St. Thomas (STT)
8/10 Very good! (2,461 reviews)
.

Reviewed on Nov 3, 2026

Villa Island Paradise

Villa Island Paradise

4 out of 5
Price was CA $8,938, price is now CA $7,246 per person
CA $7,246
per person
Dec 29 - Jan 4
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to St. Thomas (STT)
9.6/10 Exceptional! (41 reviews)
View was amazing . Unit itself was very unique

Reviewed on Sep 13, 2026

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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 St. John
The price is CA $547 per night from Nov 30 to Dec 1
CA $547
CA $615 total
Nov 30 - Dec 1
includes taxes & fees
8.4/10 Very good! (512 reviews)
"Pool was closed and under construction. No notice about it"

Reviewed on Oct 31, 2026

The Westin St. John Resort Villas
Blue Dolphin Villa Great Cruz Bay FEATURING A NEW MASTER BEDROOM gorgeous views

Blue Dolphin Villa Great Cruz Bay FEATURING A NEW MASTER BEDROOM gorgeous views

Cruz Bay St John
9.8/10 Exceptional! (87 reviews)
"We had a fantastic stay at Blue Dolphin! The hosts were excellent with communication from the start and provided great recommendations, including help with car rentals. Dwight, the property manager, was wonderful—he met us at the ferry and personally escorted us to the house to make sure we got settled ..."

Reviewed on Aug 17, 2026

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Blue Dolphin Villa Great Cruz Bay FEATURING A NEW MASTER BEDROOM gorgeous views
LAGUNA SUN Caribbean Hideaway your St. John Escape New aibnb

LAGUNA SUN Caribbean Hideaway your St. John Escape New aibnb

St john vi
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LAGUNA SUN Caribbean Hideaway your St. John Escape New aibnb
See all 544 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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Stay near popular Estate Chocolate Hole and Great Cruz Bay attractions

Chocolate Hole Beach

Why not spend a lazy afternoon at Chocolate Hole Beach during your trip to Estate Chocolate Hole and Great Cruz Bay?
See properties

What to do in Estate Chocolate Hole and Great Cruz Bay

Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT

Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT

CA $168
per adult
96% of travellers recommend
Turtle Cove Catamaran Snorkel and Sail at Little Buck Island STT
Night Kayak Tour St. Thomas - Westin Frenchman's Reef

Night Kayak Tour St. Thomas - Westin Frenchman's Reef

CA $111
per adult
96% of travellers recommend
Night Kayak Tour St. Thomas - Westin Frenchman's Reef
Jost Van Dyke - Sandy Spit & Soggy Dollar Sailing Tour in the BVI

Jost Van Dyke - Sandy Spit & Soggy Dollar Sailing Tour in the BVI

CA $322
per adult
Jost Van Dyke - Sandy Spit & Soggy Dollar Sailing Tour in the BVI
See all activities in Estate Chocolate Hole and Great Cruz Bay

Frequently asked questions

How much does an Estate Chocolate Hole and Great Cruz Bay vacation package cost?
You'll find cheap prices from CA $2,323 on Expedia for your Estate Chocolate Hole and Great Cruz Bay getaway. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Estate Chocolate Hole and Great Cruz Bay costs.
What are the cheapest months to go to Estate Chocolate Hole and Great Cruz Bay?
September, October and November are great times to search for cheap Estate Chocolate Hole and Great Cruz Bay vacation packages. Travelling in less busy months means you can generally find reduced prices on flights and hotels.
How many days is enough for Estate Chocolate Hole and Great Cruz Bay?
Estate Chocolate Hole and Great Cruz Bay vacations come in various shapes and sizes, but to get a real feel for this place, we think 4 days is about right. In this timeframe, you can fit in major attractions like Cinnamon Bay Beach and Cruz Bay Beach and track down some lesser-known spots. Don't miss out on neighbourhoods such as Estate Enighed and Estate Concordia An either. If you plan wisely, you can even allow for a day trip or two from Estate Chocolate Hole and Great Cruz Bay too.
How to find the best Estate Chocolate Hole and Great Cruz Bay package deals?
Use Expedia's filters to find some terrific Estate Chocolate Hole and Great Cruz 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 look for Estate Chocolate Hole and Great Cruz Bay package deals in the low season. Play around with your travel dates and you may score even bigger 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 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 break by booking a personalized vacation package. Click on the "Package" heading, then enter your destination and travel dates to browse some great hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Estate Chocolate Hole and Great Cruz Bay?
If you're planning a spur-of-the-moment Estate Chocolate Hole and Great Cruz Bay vacation, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Estate Chocolate Hole and Great Cruz Bay?

  1. Pick your dates: What you'd like to do in Estate Chocolate Hole and Great Cruz Bay and your preferred season can help you decide when to travel.
  2. Budget wisely: On top of the price of your hotel, you'll need to consider other expenses too. These include food, flights and transportation. Also, set aside a little extra for unexpected expenses that may arise during your trip to Estate Chocolate Hole and Great Cruz Bay.
  3. Determine how many days away: Start by compiling a list of the attractions and activities you want to get to in Estate Chocolate Hole and Great Cruz Bay. Then, estimate how long you'll need at each, as well as any travel time.
  4. Combine your accommodations and airfare: Once you've nailed down your trip dates and duration, book the perfect Estate Chocolate Hole and Great Cruz Bay vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.