Name: Secluded Oceanfront Villa with pool and incredible view! Welcome to Paradise!
Rating: 9.4

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.

At Home in the Tropics

CA $1,610

per person

May 13 - May 18

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to St. Thomas (STT)

9.8/10 Exceptional! (149 reviews)

We are repeat guests and will be back again. The owners are very warm and friendly. The hotel is the right blend of convenient and unique. Not cookie cutter at all, which is a huge plus. 5 stars!

Reviewed on Mar 3, 2026

Wharfside Village Hotel

CA $3,490

per person

Apr 6 - Apr 12

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to St. Thomas (STT)

9.8/10 Exceptional! (133 reviews)

Great location and staff. Will definitely return and highly recommend.

Reviewed on Mar 3, 2026

Limetree Beach Resort by Club Wyndham

CA $2,209

per person

May 13 - May 18

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to St. Thomas (STT)

8.2/10 Very Good! (202 reviews)

Super clean, staff was really nice. Loved that the pool closed at 10pm. Food was really good.

Reviewed on Jan 17, 2026

Margaritaville Vacation Club - St. Thomas

CA $1,893

per person

May 13 - May 18

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to St. Thomas (STT)

8/10 Very Good! (2,377 reviews)

Staff was very friendly and helpful. The hilltop bar is very laid-back and relaxing. The other pool has things going on all day to keep you entertained. There isn't that much of an option for eating on property. The restaurant food isn't good. And the coffee shop a bit overpriced. The location is great for getting to Redhook and catching the ferry to St John.

Reviewed on Mar 6, 2026

Great Bay Condominiums located at The Ritz-Carlton Club, St Thomas

CA $3,374

per person

May 13 - May 18

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to St. Thomas (STT)

9.2/10 Wonderful! (33 reviews)

Ready to book your vacation to Estate Chocolate Hole and Great Cruz Bay?

Choose your dates

Estate Chocolate Hole and Great Cruz Bay Hotel Deals

The Westin St. John Resort Villas

300B Chocolate Hole St. John

CA $997

CA $1,121 total

Mar 25 - Mar 26

includes taxes & fees

8.2/10 Very Good! (465 reviews)

Great

Reviewed on Feb 20, 2026

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

Cruz Bay St John

9.8/10 Exceptional! (80 reviews)

everything was great really good house we had a great time.

Reviewed on Jan 19, 2026

Get rates

Secluded Oceanfront Villa with pool and incredible view! Welcome to Paradise!

St John

9.4/10 Exceptional! (29 reviews)

Beautiful view. Amazing sunsets. Very clean, comfortable nice bedrooms. This was once a much larger property that was partly demolished prob after the last big hurricane. Outdoor kitchen area is pretty basic. Grill with a side burner was the only way to cook. Bring KUERIG pods from home they are ...

Reviewed on Feb 21, 2026

Get rates

See all 513 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.