A coastal town with buildings, a harbor filled with boats, and a mountainous backdrop.

Estate Chocolate Hole and Great Cruz Bay Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Estate Chocolate Hole and Great Cruz Bay vacation rentals

A resort with a central pool, palm trees, and a view of the ocean.

1. The Westin St. John Resort Villas

The Westin St. John Resort Villas
4.5 star property
St. John
8.4 out of 10, Very good, (507 reviews)
"Unfortunately, the pool was under construction during our stay and unusable, but we didn't allow that to stop us. The beach was quite and relaxing, thus Westin has a family vibe and good for children. The staff was friendly. I do think they can do better at advertising the water and children's activities. The rooms were excellent and resturants too. Ferry service and crew were great too. Great stay for a family of 5!"
United States
Shani
The price is NT$11,181
NT$12,579 total
includes taxes & fees
Oct 15 - Oct 16
The Westin St. John Resort Villas
A coastal landscape with a beach, clear blue waters, and lush greenery.

2. Villa Island Paradise

Villa Island Paradise
4.0 star property
St. John
9.6 out of 10, Exceptional, (41 reviews)
"View was amazing . Unit itself was very unique"
United States
Zach Ezekiel Azurus
The price is NT$2,937
NT$16,197 total
includes taxes & fees
Oct 11 - Oct 12
Villa Island Paradise
A room with a TV, wicker furniture, and a view of the ocean.

3. Suite St. John at Gallows Point Resort

Suite St. John at Gallows Point Resort
4.0 star property
St. John
8.8 out of 10, Excellent, (106 reviews)
"Friendly staff. Beautiful property."
United States
Sean
The price is NT$15,769
NT$23,405 total
includes taxes & fees
Oct 5 - Oct 6
Suite St. John at Gallows Point Resort
A stone building with a staircase leading to an entrance, surrounded by potted plants and a clear sky.

4. Bluebeard's Castle Resort

Bluebeard's Castle Resort
4.0 star property
Charlotte Amalie
9.0 out of 10, Wonderful, (867 reviews)
"Bluebeards is one of my favorite places to stay when I am on the island."
United States
Erica
The price is NT$5,878
NT$7,275 total
includes taxes & fees
Nov 1 - Nov 2
Bluebeard's Castle Resort
A balcony with a table, chairs, and a view of a turquoise sea and green hills.

5. Peter Bay Gatehouse

Peter Bay Gatehouse
4.0 star property
Maho Bay Quarter
8.2 out of 10, Very good, (21 reviews)
"Outstanding view from the villa"
United States
Thomas
The price is NT$19,910
NT$27,775 total
includes taxes & fees
Oct 4 - Oct 5
Peter Bay Gatehouse
A living room with a sofa, chairs, a lamp, and a painting on the wall.

6. The Landmark Apartment

The Landmark Apartment
2.5 star property
St. Thomas
8.6 out of 10, Excellent, (18 reviews)
"Wonderful place to stay and Ali the cab driver was also amazing "
United States
Eileen
The price is NT$7,084
NT$12,748 total
includes taxes & fees
Oct 5 - Oct 6
The Landmark Apartment
A spacious living area with a sofa, dining table, and chairs, overlooking a scenic ocean view.

7. The Breeze

The Breeze
2.0 star property
ST Thomas
The price is NT$4,190
NT$23,828 total
includes taxes & fees
Oct 9 - Oct 10
The Breeze
A room with two wicker chairs with blue cushions, a small table with a vase, and a door with a keyhole.

8. The Perch at Hawk Hill

The Perch at Hawk Hill
2.0 star property
St. Thomas
The price is NT$5,483
NT$10,947 total
includes taxes & fees
Oct 3 - Oct 4
The Perch at Hawk Hill
A balcony with a view of a coastal town, a table, and a chair.

9. Little Indigo Apartments

Little Indigo Apartments
3.5 star property
St. Thomas
7.8 out of 10, Good, (30 reviews)
"The apartment had an amazing view. It was clean and well prepared prior to our arrival. I look forward to our next visit."
United States
Lynda
The price is NT$5,419
NT$9,891 total
includes taxes & fees
Oct 9 - Oct 10
Little Indigo Apartments
A bedroom with a bed, a nightstand, a lamp, and a view through a door.

10. Aqua

Aqua
3.0 star property
St. Thomas
9.4 out of 10, Exceptional, (8 reviews)
"Comfortable and beautiful area"
United States
Paola
The price is NT$7,139
NT$12,808 total
includes taxes & fees
Nov 1 - Nov 2
Aqua
A bedroom with a bed, a chair, a nightstand, a lamp, and a window with blinds.

11. The Cottage at Villa Indigo

The Cottage at Villa Indigo
3.0 star property
St. Thomas
8.8 out of 10, Excellent, (15 reviews)
"We got a true dose of the life experience on the island staying here. The entire experience was MAGICAL!!!! Me and my family will most definitely staying again when we come back "
United States
Oronde
The price is NT$7,999
NT$13,881 total
includes taxes & fees
Oct 31 - Nov 1
The Cottage at Villa Indigo
A balcony with two wicker chairs and a small round table, surrounded by a white railing, overlooking a lush green landscape with hills in the background.

12. Villa Indigo 1BR in Private Gated Estate

Villa Indigo 1BR in Private Gated Estate
3.5 star property
St. Thomas
8.8 out of 10, Excellent, (33 reviews)
"Excellent place"
United States
Trent
The price is NT$6,941
NT$11,775 total
includes taxes & fees
Oct 30 - Oct 31
Villa Indigo 1BR in Private Gated Estate
A beachfront hotel with multiple colorful buildings, a sandy beach, and rows of sun loungers with umbrellas.

13. Marriott's Frenchman's Cove

Marriott's Frenchman's Cove
4.0 star property
St. Thomas
9.0 out of 10, Wonderful, (207 reviews)
"The property is well maintained and comfortable. Our family enjoyed the private beach and the pool. The one on-site restaurant serves a variety of good food."
United States
Cathryn
The price is NT$20,547
NT$23,116 total
includes taxes & fees
Oct 15 - Oct 16
Marriott's Frenchman's Cove
A swimming pool with lounge chairs and a view of the ocean.

14. St Thomas Cliffside Villa With Pool & Hot Tub!

St Thomas Cliffside Villa With Pool & Hot Tub!
3.5 star property
St. Thomas
The price is NT$20,388
NT$36,088 total
includes taxes & fees
Oct 11 - Oct 12
St Thomas Cliffside Villa With Pool & Hot Tub!
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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Top Estate Chocolate Hole and Great Cruz Bay Hotel Reviews

The Westin St. John Resort Villas

The Westin St. John Resort Villas

10/10 Excellent
"Unfortunately, the pool was under construction during our stay and unusable, but we didn't allow that to stop us. The beach was quite and relaxing, thus Westin has a family vibe and good for children. The staff was friendly. I do think they can do better at advertising the water and children's activities. The rooms were excellent and resturants too. Ferry service and crew were great too. Great stay for a family of 5!"
Shani 6-night trip
Posted 3 weeks ago
The Westin St. John Resort Villas

Find out more about Estate Chocolate Hole and Great Cruz Bay

Search for holiday rentals in Estate Chocolate Hole and Great Cruz Bay on Expedia! You can easily find your home rentals, villas, holiday apartments in Estate Chocolate Hole and Great Cruz Bay using one of the methods below:

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Frequently asked questions

Can I find vacation rentals in Estate Chocolate Hole and Great Cruz Bay?

Yes, we have vacation rentals near well known points of interest in Estate Chocolate Hole and Great Cruz Bay, or you can go with a more secluded option if you're looking for a relaxing stay.

How many vacation rentals are there in Estate Chocolate Hole and Great Cruz Bay?

Choose from 54 Expedia vacation rentals in Estate Chocolate Hole and Great Cruz Bay for a memorable vacation.

What can I see and do in Estate Chocolate Hole and Great Cruz Bay?

Chocolate Hole and Great Cruz Bay are a couple of lovely local spots to get outside and enjoy nature. While here, Chocolate Hole Beach and Rendezvous Bay are other places worth a visit.

What are vacation rentals like in Estate Chocolate Hole and Great Cruz Bay?

A vacation rental is a private property where you can stay for several days or longer in Estate Chocolate Hole and Great Cruz Bay. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a small group gathering.