Search Deals onWindward Vacation Packages
Windward Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Manapany
Anse des Cayes
Save 100% on your flight
Price was $5,393, price is now $3,624 per person
$3,624
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Gustavia (SBH)
Stay at this 5-star luxury hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Gustavia Harbor and Anse des Cayes Beach are located nearby.
Tropical Hotel St Barth
Save 100% on your flight
Price was $6,562, price is now $4,626 per person
$4,626
per person
Dec 13 - Dec 20
found 19 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Gustavia (SBH)
Stay at this 5-star luxury hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free valet parking. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Gustavia Harbor and St. Jean Beach are located nearby.
Le Toiny Hôtel & Beach Club
Price was $6,682, price is now $5,558 per person
$5,558
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Gustavia (SBH)
Stay at this 5-star luxury hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Gustavia Harbor and Petit Cul de Sac Beach are located nearby.
Christopher Hotel
Price was $6,718, price is now $5,860 per person
$5,860
per person
Nov 22 - Nov 29
found 22 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Gustavia (SBH)
Stay at this 5-star luxury hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Gustavia Harbor and Marigot Beach are located nearby.
Hotel Barrière Le Carl Gustaf St Barth
Lurin
Save 100% on your flight
Price was $7,852, price is now $6,918 per person
$6,918
per person
Dec 15 - Dec 20
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Gustavia (SBH)
Stay at this 5-star luxury hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free valet parking. Popular attractions Gustavia Harbor and Shell Beach are located nearby.
GYP SEA Saint Barth
Price was $8,687, price is now $7,987 per person
$7,987
per person
Nov 22 - Nov 29
found 22 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Gustavia (SBH)
Stay at this 5-star luxury hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free valet parking. Popular attractions Gustavia Harbor and Flamands Beach are located nearby.
Le Barthélemy Hotel & Spa
Price was $9,326, price is now $8,896 per person
$8,896
per person
Dec 13 - Dec 20
found 19 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Gustavia (SBH)
Stay at this 5-star luxury hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free valet parking. Popular attractions Gustavia Harbor and Grand Cul de Sac are located nearby.
3-4 Night Vacations in Windward
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Windward
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Windward
Christopher Hotel
Pointe Milou, 9, St. Barthelemy
Stay at this 5-star luxury hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
Tropical Hotel St Barth
Les Hauts de Saint Jean, St. Barthelemy
Stay at this 5-star luxury hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free valet parking. Our guests praise the helpful staff and the property ...
Rosewood Le Guanahani St Barth
Grand Cul De Sac, St. Barthelemy
Book a stay at this beach hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Gustavia Harbor and Grand Cul de Sac ...
Save an average of 15% on thousands of hotels when you're signed in
Le Barthélemy Hotel & Spa
Baie de Grand Cul de Sac, St. Barthelemy
Stay at this 5-star luxury hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free valet parking. Popular attractions Gustavia Harbor and Grand Cul ...
Le Toiny Hôtel & Beach Club
1 Rue du Toiny, St. Barthelemy
Stay at this 5-star luxury hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Gustavia Harbor and Petit Cul de Sac ...
Amnios St Barth
Lagon de Grand-Cul-de Sac, St. Barthelemy
Book a stay at this boutique hotel in St. Barthelemy. Enjoy free breakfast, free parking, and a free airport shuttle. Popular attractions Gustavia Harbor and ...
Le Sereno
Grand Cul de Sac BP 19, St. Barthelemy
Stay at this 5-star luxury hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Gustavia Harbor and Grand Cul de Sac ...
Hotel Les Ondines Sur La Plage
Grand Cul De Sac Plage, St. Barthelemy
Book a stay at this beach hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
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.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Fri, Nov 14 - Mon, Nov 17
SXM
Princess Juliana Intl.
SBH
Gustaf III
$293 Roundtrip, found 6 days ago
$293
Roundtrip
found 6 days ago
Fri, Nov 14 - Mon, Nov 17
SXM
Princess Juliana Intl.
SBH
Gustaf III
$303 Roundtrip, found 6 days ago
$303
Roundtrip
found 6 days ago
Tue, Nov 11 - Mon, Nov 17
SXM
Princess Juliana Intl.
SBH
Gustaf III
$310 Roundtrip, found 6 days ago
$310
Roundtrip
found 6 days ago
Fri, Nov 14 - Mon, Nov 17
SXM
Princess Juliana Intl.
SBH
Gustaf III
$313 Roundtrip, found 6 days ago
$313
Roundtrip
found 6 days ago
