Name: Windward Passage Hotel
Price range: CA $233

Your Estate Haulover Vacation

An easy way to experience this city is with a custom-made Estate Haulover vacation package. Stay in the neighborhood of Wickhams Cay 1, which is good for views, dining and shopping or choose someplace else — our package deals are all about you. Any trip to Estate Haulover needs a well-designed itinerary. Fill yours with big-name attractions like Trunk Bay, Annaberg Plantation and Cinnamon Bay Beach. Don't put off exploring this destination any longer. Your perfect Estate Haulover vacation is a few quick clicks away with Expedia.

Top Estate Haulover Vacation Deals

Price found within the past 48 hours. Click for updated prices.

Windward Passage Hotel

CA $1,133

per person

Oct 7 - Oct 11

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to St. Thomas (STT)

7/10 Good! (1,378 reviews)

Property is okay, it’s a good looking to walk around to lots of shops and restaurants but not much on property itself.

Reviewed on Sep. 1, 2025

Margaritaville Vacation Club - St. Thomas

CA $2,574

per person

Nov 9 - Nov 16

found 3 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to St. Thomas (STT)

8/10 Very Good! (2,213 reviews)

Great rooftop pool!

Reviewed on Sep. 3, 2025

The Hideaway Hull Bay

CA $4,598

per person

Nov 9 - Nov 16

found 3 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to St. Thomas (STT)

9.6/10 Exceptional! (51 reviews)

I loved this resort, if you are looking for a true island experience Hideaway Bay is for you. Located on the north side of the island, off the beaten path. The tranquility of the resort is fantastic. I hardly saw any other travelers on the resort. I would recommend this resort for deep relaxation and rest. Hideaway would also make a great honeymoon destination!

Reviewed on Jul. 31, 2025

Club Wyndham Elysian Beach Resort

CA $2,698

per person

Nov 9 - Nov 16

found 3 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to St. Thomas (STT)

7.8/10 Good! (163 reviews)

Clean room. Staff are very slow if you need towels or a refill on shampoo or body wash or staff just doesn’t answer when you call the desk

Reviewed on Sep. 3, 2025

At Home in the Tropics

CA $2,408

per person

Nov 9 - Nov 16

found 3 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to St. Thomas (STT)

9.8/10 Exceptional! (148 reviews)

The property managers made me feel very welcomed and this property stays locked so me and my girlfriend felt very safe the entire trip. Planning on saving more money and will come back to visit asap. Would recommend to anyone and everyone visiting st Thomas

Reviewed on Jul. 21, 2025

Ready to book your vacation to Estate Haulover?

Choose your dates

Estate Haulover Hotel Deals

Margaritaville Vacation Club - St. Thomas

6080 Estate Smith Bay, St. Thomas

CA $371

CA $417 total

Sep 5 - Sep 6

includes taxes & fees

The Westin St. Thomas Beach Resort & Spa

5 Estate Bakkeroe, Po Box 7100, St. Thomas, St. Thomas

Fully refundableReserve now, pay when you stay

CA $330

CA $483 total

Sep 18 - Sep 19

includes taxes & fees

Windward Passage Hotel

Veterans Drive Charlotte Amali, Po Box 640, St. Thomas, St. Thomas

Fully refundableReserve now, pay when you stay

CA $233

CA $285 total

Sep 5 - Sep 6

includes taxes & fees

See all 3,738 properties in Estate Haulover

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.