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

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Estate Chocolate Hole and Great Cruz Bay holiday 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, (509 reviews)
"Everything was amazing! It will always be my go to when I come to visit."
United States
Treacy
The price is 9.081.072 ₫
10.216.219 ₫ total
includes taxes & fees
25 Oct - 26 Oct
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 2.728.357 ₫
13.563.443 ₫ total
includes taxes & fees
16 Oct - 17 Oct
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 16.687.440 ₫
23.592.936 ₫ total
includes taxes & fees
12 Oct - 13 Oct
Suite St. John at Gallows Point Resort
A balcony with a table, chairs, and a view of a turquoise sea and green hills.

4. 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 20.257.776 ₫
27.156.027 ₫ total
includes taxes & fees
12 Oct - 13 Oct
Peter Bay Gatehouse
A stone building with a staircase leading to an entrance, surrounded by potted plants and a clear sky.

5. Bluebeard's Castle Resort

Bluebeard's Castle Resort
4.0 star property
Charlotte Amalie
9.0 out of 10, Wonderful, (892 reviews)
"Property was very clean and a beautiful place to stay."
United States
Freo
The price is 4.774.160 ₫
5.908.023 ₫ total
includes taxes & fees
9 Nov - 10 Nov
Bluebeard's Castle Resort
A beachfront hotel with multiple colorful buildings, a sandy beach, and rows of sun loungers with umbrellas.

6. 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 14.462.448 ₫
16.270.254 ₫ total
includes taxes & fees
16 Oct - 17 Oct
Marriott's Frenchman's Cove
A beach with clear turquoise water, rocky shoreline, and a distant view of a hill with buildings.

7. Oceanview Retreat at Point Pleasant, Virgin Island

Oceanview Retreat at Point Pleasant, Virgin Island
3.0 star property
St. Thomas
The price is 3.415.104 ₫
10.599.500 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Oceanview Retreat at Point Pleasant, Virgin Island
A bedroom with a bed, a nightstand, a lamp, and a view through a door.

8. 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 5.797.915 ₫
10.402.452 ₫ total
includes taxes & fees
28 Oct - 29 Oct
Aqua
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 4.400.827 ₫
8.033.225 ₫ total
includes taxes & fees
12 Oct - 13 Oct
Little Indigo Apartments
A spacious living area with a sofa, dining table, and chairs, overlooking a scenic ocean view.

10. The Breeze

The Breeze
2.0 star property
ST Thomas
The price is 3.403.074 ₫
19.351.658 ₫ total
includes taxes & fees
12 Oct - 13 Oct
The Breeze
A room with two wicker chairs with blue cushions, a small table with a vase, and a door with a keyhole.

11. The Perch at Hawk Hill

The Perch at Hawk Hill
2.0 star property
St. Thomas
The price is 4.453.427 ₫
8.890.906 ₫ total
includes taxes & fees
12 Oct - 13 Oct
The Perch at Hawk Hill
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 5.637.250 ₫
9.563.297 ₫ total
includes taxes & fees
12 Oct - 13 Oct
Villa Indigo 1BR in Private Gated Estate
A bedroom with a bed, a chair, a nightstand, a lamp, and a window with blinds.

13. 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 6.496.459 ₫
11.273.368 ₫ total
includes taxes & fees
5 Nov - 6 Nov
The Cottage at Villa Indigo
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 16.558.080 ₫
29.309.354 ₫ total
includes taxes & fees
16 Oct - 17 Oct
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
"Everything was amazing! It will always be my go to when I come to visit."
Treacy 4-night trip
Posted 1 day ago
The Westin St. John Resort Villas

Frequently asked questions

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

Yes, there are holiday rentals close to the most popular sights in Estate Chocolate Hole and Great Cruz Bay, or you can select a more secluded option if you're looking for a relaxing stay.

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

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

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 holiday rentals like in Estate Chocolate Hole and Great Cruz Bay?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Estate Chocolate Hole and Great Cruz Bay. Holiday rentals provide amenities like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for family trips.