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

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, (508 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 P22,050
P24,806 total
includes taxes & fees
Oct 24 - Oct 25
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 P4,345
P30,141 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 P40,520
P57,287 total
includes taxes & fees
Oct 12 - Oct 13
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 P49,189
P65,939 total
includes taxes & fees
Oct 21 - Oct 22
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, (890 reviews)
"Property was very clean and a beautiful place to stay."
United States
Freo
The price is P11,592
P14,346 total
includes taxes & fees
Nov 8 - Nov 9
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 P35,117
P39,507 total
includes taxes & fees
Oct 16 - Oct 17
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 P8,302
P25,766 total
includes taxes & fees
Nov 1 - Nov 2
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 P14,078
P25,259 total
includes taxes & fees
Nov 10 - Nov 11
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 P10,686
P19,506 total
includes taxes & fees
Oct 24 - Oct 25
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 P8,263
P46,989 total
includes taxes & fees
Oct 12 - Oct 13
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 P10,814
P21,588 total
includes taxes & fees
Oct 12 - Oct 13
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 P13,688
P23,221 total
includes taxes & fees
Nov 10 - Nov 11
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 P15,774
P27,373 total
includes taxes & fees
Oct 31 - Nov 1
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 P40,205
P71,167 total
includes taxes & fees
Oct 14 - Oct 15
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

8/10 Good
"Beautiful resort, excellent staff. Room - one bedroom, 2 bathrooms, kitchen, living room, washer and dryer was great. Restaurant (Lemongrass) food was just ok and expensive. Better to go downtown. Downtown was decent. Lemongrass Bar at the Westin - very slow service. If you plan on having more than one drink - Order 2 at a time. Pool was closed for repairs but they warned us before time. Besides we went there for the beach. Trunk Bay was nice but we enjoyed and loved Maho Bay- food truck had excellent food. Recommend purchasing some food (specifically breakfast) and drinks to keep at the room. Best to purchase from St Thomas (prices are better)"
Jose 4-night trip
Posted 1 day 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.