Windward Vacations & Trips from $4,240
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The Latest Windward Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Tropical Hotel St Barth
Save 100% on your flight
Price was $6,600, price is now $4,240 per person
$4,240
per person
Apr 5 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Gustavia (SBH)
9.8/10 Exceptional! (94 reviews)
The service was excellent - especially the concierge. The staff was friendly and always accommodating. The hotel was beautiful; room was spotless and comfortable. We enjoyed the breakfast thoroughly! Would recommend to everyone!
Reviewed on Feb 12, 2026
Hotel Manapany
Anse des Cayes
Save 100% on your flight
Price was $7,338, price is now $4,746 per person
$4,746
per person
Apr 5 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Gustavia (SBH)
9.4/10 Exceptional! (66 reviews)
The property was exquisite. The entire staff was incredible, especially Noémie from Reception. She went above and beyond to make our 11th anniversary very memorable. I am already looking forward to a more extended visit to Hotel Manapany.
Reviewed on Jun 15, 2025
Le Toiny Hôtel & Beach Club
Save 100% on your flight
Price was $10,601, price is now $7,642 per person
$7,642
per person
Apr 5 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Gustavia (SBH)
9.8/10 Exceptional! (44 reviews)
It was perfect . It’s a beautiful property and the service was a dream. They thought about and catered to everything proactively.
Reviewed on Aug 4, 2025
Le Barthélemy Hotel & Spa
Save 100% on your flight
Price was $13,912, price is now $10,987 per person
$10,987
per person
Apr 5 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Gustavia (SBH)
9.8/10 Exceptional! (77 reviews)
Staff-10/10
Food-10/10
Amenities-10/10
Only thing Le Barthelemy - wish they use cooling bedsheets. Or comforters - that are less warm.
Reviewed on Dec 15, 2025
Find the Best Windward Vacation Packages
Windward Essential Information
Language | French |
|---|---|
Currency | Euros |
Local Welcome | Salut / Bonjour |
Local Goodbye | Au revoir / À bientôt |
Closest Airport | Gustaf III Airport (SBH) |
Windward Hotel Deals
Christopher Hotel
Pointe Milou, 9 St. Barthelemy
$1,808 nightly
The price is $1,893 total per night from Mar 18 to Mar 19
$1,893 total
Mar 18 - Mar 19
Total with taxes and fees
9.6/10 Exceptional! (230 reviews)
Great rooms, service and amenities!
Reviewed on Jan 19, 2026
Tropical Hotel St Barth
Les Hauts de Saint Jean St. Barthelemy
$1,094 nightly
The price is $1,149 total per night from Mar 24 to Mar 25
$1,149 total
Mar 24 - Mar 25
Total with taxes and fees
9.8/10 Exceptional! (103 reviews)
The service was excellent - especially the concierge. The staff was friendly and always accommodating. The hotel was beautiful; room was spotless and comfortable. We enjoyed the breakfast thoroughly! Would recommend to everyone!
Reviewed on Feb 12, 2026
Rosewood Le Guanahani St Barth
Grand Cul De Sac St. Barthelemy
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.
Discover the most popular places to visit in Windward
Lorient Beach
Why not spend a carefree afternoon at Lorient Beach during your travels in Quartier Lorient? You can enjoy the restaurants while in the area.
Gouverneur Beach
Why not spend a carefree afternoon at Gouverneur Beach during your travels in Anse du Gouverneur?
Saline Beach
Why not spend a carefree afternoon at Saline Beach during your travels in Morne Rouge?
What to do in Windward
Edge Ferry Tickets to St. Barts
$100
per adult
84% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.