Search Deals onWindward Vacation Packages
Windward Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Christopher Hotel
per person
Feb 15 - Feb 20
found 16 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 parking. Our guests praise the helpful staff in our reviews. Popular attractions Gustavia Harbor and Marigot Beach are located nearby.
Hotel Manapany
Anse des Cayes
Save 100% on your flight
per person
Feb 6 - Feb 13
found 1 day 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. Popular attractions Gustavia Harbor and Anse des Cayes Beach are located nearby.
Hotel le Toiny
Save 100% on your flight
per person
Feb 6 - Feb 13
found 1 day 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. Popular attractions Gustavia Harbor and Petit Cul de Sac Beach are located nearby.
GYP SEA Saint Barth
Save 100% on your flight
per person
Feb 6 - Feb 13
found 1 day 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.
Hotel Barrière Le Carl Gustaf St Barth
Lurin
per person
Feb 8 - Feb 15
found 1 day 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 Plage du Grand Galet are located nearby.
Le Barthélemy Hotel & Spa
Save 100% on your flight
per person
Feb 23 - Mar 1
found 20 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 ...
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 ...
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 ...
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 ...
Tropical Hotel St Barth
Baie de St. Jean, St. Barthelemy
Book a stay at this beach hotel in St. Barthelemy. Enjoy free WiFi, free valet parking, and a 24-hour front desk. Our guests praise the helpful staff and the ...
Hotel Villa Lodge 4 épices
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 ...
Hotel le Toiny
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 ...
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.
Mon, Mar 3 - Mon, Mar 3
SXM
Princess Juliana Intl.
SBH
Gustaf III
$282 Roundtrip, found 18 hours ago
$282
Roundtrip
found 18 hours ago
Tue, Apr 15 - Tue, Apr 22
EWR
Newark Liberty Intl. Airport
SBH
Gustaf III
$894 Roundtrip, found 5 days ago
$894
Roundtrip
found 5 days ago
Tue, Mar 11 - Sun, Mar 16
MIA
Miami Intl.
SBH
Gustaf III
$1,009 Roundtrip, found 5 days ago
$1,009
Roundtrip
found 5 days ago
Sun, Jan 12 - Thu, Jan 16
ATL
Hartsfield-Jackson Atlanta Intl.
SBH
Gustaf III
$1,642 Roundtrip, found 22 hours ago
$1,642
Roundtrip
found 22 hours ago