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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

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

Outdoor pool, pool cabanas (surcharge), pool loungers

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, (502 reviews)
"We had a good stay at the Westin in St. John. Service is slow in the resort other than that everything else was good."
United States
Rituparna
The price is ฿12,348
฿13,892 total
includes taxes & fees
2 Sept - 3 Sept
The Westin St. John Resort Villas
Luxury Suite Ocean View Upper 15D | View from room

2. 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 ฿16,387
฿24,221 total
includes taxes & fees
15 Aug - 16 Aug
Suite St. John at Gallows Point Resort
Aerial view

3. Villa Island Paradise

Villa Island Paradise
4.0 star property
St. John
9.6 out of 10, Exceptional, (36 reviews)
"Beautiful location with stunning views and a peaceful atmosphere. The room was clean and comfortable, and the staff was friendly and helpful throughout the stay. Great option for a relaxing getaway in St. John."
United States
Quoc Phong Eric
The price is ฿1,416
฿17,317 total
includes taxes & fees
15 Aug - 16 Aug
Villa Island Paradise
Exterior

4. Bluebeard's Castle Resort

Bluebeard's Castle Resort
4.0 star property
Charlotte Amalie
9.0 out of 10, Wonderful, (733 reviews)
"The view, the accommodation, the staff were all superb. I always stay there when I visit the Island."
United States
Janice
The price is ฿6,109
฿8,232 total
includes taxes & fees
12 Sept - 13 Sept
Bluebeard's Castle Resort
Children’s activities

5. Sunset Ridge Villas Unit D

Sunset Ridge Villas Unit D
3.5 star property
St. John
9.4 out of 10, Exceptional, (3 reviews)
"This property was excellent especially for us a family of 4 with teenage kids. The space was great and the location was easy enough to get to. The amenities were excellent, from a fully outfitted kitchen to great beach resources such as chairs, cooler & snorkel equipment. "
United States
Jessica
The price is ฿7,466
฿21,148 total
includes taxes & fees
6 Sept - 7 Sept
Sunset Ridge Villas Unit D
Luxury Penthouse | Balcony view

6. Peter Bay Gatehouse

Peter Bay Gatehouse
4.0 star property
Maho Bay Quarter
8.4 out of 10, Very good, (20 reviews)
"Outstanding view from the villa"
United States
Thomas
The price is ฿20,691
฿28,864 total
includes taxes & fees
15 Aug - 16 Aug
Peter Bay Gatehouse
Beach nearby, snorkelling

7. Marriott's Frenchman's Cove

Marriott's Frenchman's Cove
4.0 star property
St. Thomas
9.0 out of 10, Wonderful, (205 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 ฿20,823
฿23,426 total
includes taxes & fees
22 Aug - 23 Aug
Marriott's Frenchman's Cove
Deluxe House, Ocean View | Living area

8. The Breeze

The Breeze
2.0 star property
ST Thomas
The price is ฿4,354
฿25,197 total
includes taxes & fees
15 Aug - 16 Aug
The Breeze
Villa (3 Bedrooms) | Interior

9. 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 ฿21,187
฿40,837 total
includes taxes & fees
27 Aug - 28 Aug
St Thomas Cliffside Villa With Pool & Hot Tub!
Family Apartment, Ocean View | Terrace/patio

10. The Perch at Hawk Hill

The Perch at Hawk Hill
2.0 star property
St. Thomas
The price is ฿5,698
฿11,946 total
includes taxes & fees
15 Aug - 16 Aug
The Perch at Hawk Hill
Terrace/patio

11. Shibui Cove

Shibui Cove
2.0 star property
St. Thomas
7.4 out of 10, Good, (6 reviews)
"Not everything was operational in the apt. Lights/fans etc. but was an awesome place to stay."
United States
William Eric
The price is ฿2,657
฿8,220 total
includes taxes & fees
27 Aug - 28 Aug
Shibui Cove
Luxury Apartment, 1 Bedroom, Sea Facing | 1 bedroom, Egyptian cotton sheets, premium bedding, down duvets

12. 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 ฿7,419
฿13,210 total
includes taxes & fees
27 Aug - 28 Aug
Aqua
Panoramic Apartment, 2 Bedrooms, Harbor View, Sea Facing, Apt#3 | Terrace/patio

13. 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 ฿5,631
฿10,209 total
includes taxes & fees
27 Aug - 28 Aug
Little Indigo Apartments
City Apartment, 3 Bedrooms, Kitchen, City View | Living room | 45-inch TV with digital channels, Netflix, Hulu

14. 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 ฿7,362
฿13,248 total
includes taxes & fees
23 Aug - 24 Aug
The Landmark Apartment
Cottage | 2 bedrooms, premium bedding, down duvets, pillow-top beds

15. 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 ฿8,909
฿15,051 total
includes taxes & fees
27 Aug - 28 Aug
The Cottage at Villa Indigo
Deluxe Apartment | Balcony

16. 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 ฿6,853
฿11,705 total
includes taxes & fees
27 Aug - 28 Aug
Villa Indigo 1BR in Private Gated Estate
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
"The property is beautiful and well kept. The service was altogether very slow but very friendly. Just be prepared for waiting for food on property. The room was amazing but had to call a couple times to get it cleaned. All in all would totally recommend and would go back again."
Heather 5-night trip
Posted 1 hour 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 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 56 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. Trunk Bay and Virgin Islands National Park are other popular places to visit in the area.

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.