
Vacations Close To Maho Bay
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Maho Bay Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.

Windward Passage Hotel
Price was $1,279, price is now $1,050 per person
$1,050
per person
Jan 4 - Jan 8
found 11 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
Very noisy (traffic). Front desk was not helpful at all. Night desk clerk told us that the restaurant was open for breakfast and to get the French Toast. Went to the restaurant and it was closed. Front desk said that it was closed because of low season (November?). The security staff were all excellent with good recommendations and wanting to help.
Will not stay here again. Not worth it.
Reviewed on Nov 11, 2026



The Mary Anne Boutique Hotel USVI
Price was $1,632, price is now $1,342 per person
$1,342
per person
Jan 4 - Jan 8
found 11 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
The pool area was under construction while we were there. The place was very nice overall and the pillows and bed were very comfortable! Would definitely recommend this place!
Reviewed on Nov 9, 2026

Buoy Haus Beach Resort St. Thomas, Autograph Collection
Price was $2,914, price is now $2,455 per person
$2,455
per person
Jan 4 - Jan 8
found 11 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
The location and the hotel and pools are beautiful, but the staff in the restaurants are not consistent, especially for the price you pay to stay, the taxes, cost of food and service charges. They are slow and forgetful. Abby at the Salt Shack and Shelby at Isla Blue were two standouts when it came to guest service in the restaurants. On afternoon 3, the bellman brought two guests to take our room. We had the do not disturb on the door and it was uncomfortable for all parties involved. Not sure how that happens.
Reviewed on Nov 9, 2026


The Cottage at Villa Indigo
Price was $1,552, price is now $1,349 per person
$1,349
per person
Jan 4 - Jan 8
found 11 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
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

Wharfside Village Hotel
Price was $2,621, price is now $2,305 per person
$2,305
per person
Jan 4 - Jan 8
found 11 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to St. Thomas (STT)
The room was awesome, the staff was awesome and the whole resort was clean as it could be. They did have construction going on which made it a little tight walking by the new building and the existing building but it didn’t cause us any problems. I’d go back tomorrow if I could take more time off work. We will be going back.
Reviewed on Nov 8, 2026
Best Lodging Options Near Maho Bay
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.
