Name: Windward Passage Hotel
Price range: CA $232
Rating: 7

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.

Limetree Beach Resort by Club Wyndham

CA $1,344

per person

Nov 1 - Nov 4

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to St. Thomas (STT)

8.2/10 Very Good! (195 reviews)

Room very cute and accommodating. Me and my husband brought our 21 yr old daughter and it was nice that our king size bed was in the loft area so our daughter had the downstairs area with the pull out sofa and balcony to give her space as well. The only negative of the room was the carpet had a couple of stains that should have been treated/cleaned.

Reviewed on Aug. 18, 2025

The Hideaway Hull Bay

CA $3,472

per person

Nov 16 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) 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

Hotel 1829

CA $1,998

per person

Nov 16 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to St. Thomas (STT)

9.6/10 Exceptional! (5 reviews)

The Cottage at Villa Indigo

CA $1,710

per person

Nov 16 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to St. Thomas (STT)

8.8/10 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

Reviewed on May 26, 2025

Windward Passage Hotel

CA $1,493

per person

Oct 12 - Oct 15

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to St. Thomas (STT)

7/10 Good! (1,378 reviews)

The room we stayed in was updated compared to a previous stay in 2024 where the room was moldy, dusty and dated.

Reviewed on Aug. 27, 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 $320

CA $360 total

Sep 1 - Sep 2

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 $343

CA $497 total

Sep 13 - Sep 14

includes taxes & fees

8.2/10 Very Good! (1,025 reviews)

"The property was beautiful and clean. Comfortable room with a beautiful view"

Reviewed on Aug. 25, 2025

Windward Passage Hotel

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

Fully refundableReserve now, pay when you stay

CA $232

CA $284 total

Aug 31 - Sep 1

includes taxes & fees

7/10 Good! (1,380 reviews)

"Windward was a great choice for my stay on the beautiful Island of St Thomas. I've enjoyed the love resort stafff, amenities, free breakfast, convience of being able to walk and fulfil all of my shopping needs."

Reviewed on Aug. 27, 2025

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.