Vacation Packages to Windward for 2026
Windward Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
GYP SEA Saint Barth
Colombier
Price was $2,621, price is now $2,313 per person
$2,313
per person
Aug 3 - Aug 7
found 17 hours ago
Roundtrip flight included
Washington (DCA) to Gustavia (SBH)
Book a stay at this luxury hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free valet parking. Popular attractions Gustavia Harbor and Flamands Beach are located nearby.
Tropical Hotel St Barth
Saint-Jean
Price was $3,223, price is now $2,445 per person
$2,445
per person
Aug 3 - Aug 7
found 17 hours ago
Roundtrip flight included
Washington (DCA) to Gustavia (SBH)
Book a stay at this luxury hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free valet parking. Our guests praise the helpful staff in our reviews. Popular attractions Gustavia Harbor and St. Jean Beach are located nearby.
Hotel Manapany
Anse des Cayes
Price was $3,639, price is now $2,951 per person
$2,951
per person
Aug 3 - Aug 7
found 17 hours ago
Roundtrip flight included
Washington (DCA) to Gustavia (SBH)
Book a stay at this 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.
Le Toiny Hôtel & Beach Club
Toiny
Price was $3,862, price is now $3,313 per person
$3,313
per person
Aug 3 - Aug 7
found 17 hours ago
Roundtrip flight included
Washington (DCA) to Gustavia (SBH)
Book a stay at this 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.
Le Barthélemy Hotel & Spa
Grand Cul-de-Sac
Price was $4,785, price is now $4,276 per person
$4,276
per person
Aug 3 - Aug 7
found 17 hours ago
Roundtrip flight included
Washington (DCA) to Gustavia (SBH)
Book a stay at this 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.
Christopher Hotel
Pointe Milou
Price was $2,868, price is now $2,630 per person
$2,630
per person
Aug 3 - Aug 7
found 17 hours ago
Roundtrip flight included
Washington (DCA) to Gustavia (SBH)
Book a stay at this 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.
Top Hotel Deals
Christopher Hotel
Pointe Milou, 9 St. Barthelemy
1.7 km from city center
Book a stay at this 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
2.08 km from city center
Book a stay at this luxury hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Gustavia Harbor and Grand Cul de Sac ...
Le Barthélemy Hotel & Spa
Baie de Grand Cul de Sac St. Barthelemy
1.86 km from city center
Book a stay at this 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
Les Hauts de Saint Jean St. Barthelemy
1.77 km from city center
Book a stay at this luxury hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free valet parking. Our guests praise the helpful staff in our reviews. ...
Le Toiny Hôtel & Beach Club
1 Rue du Toiny St. Barthelemy
2.13 km from city center
Book a stay at this 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
1.8 km from city center
Book a stay at this boutique hotel in St. Barthelemy. Enjoy free parking, breakfast (surcharge), and room service. Popular attractions Gustavia Harbor and Grand ...
Lil' Home
548 Route de Dévêt, Devet St. Barthelemy
1.28 km from city center
Stay at this cottage in St. Barthelemy. Enjoy free WiFi, free parking, and private plunge pools. Popular attractions Gustavia Harbor and Grand Cul de Sac are ...
Le Sereno
Grand Cul de Sac BP 19 St. Barthelemy
1.92 km from city center
Book a stay at this 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
1.9 km from city center
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
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Thu, Nov 26 - Sat, Dec 5
EWR
New York
SBH
Gustavia
$1,229 Roundtrip, found 4 days ago
$1,229
Roundtrip
found 4 days ago
Thu, Nov 26 - Sat, Dec 5
EWR
New York
SBH
Gustavia
$1,244 Roundtrip, found 4 days ago
$1,244
Roundtrip
found 4 days ago
Thu, Nov 26 - Sat, Dec 5
EWR
New York
SBH
Gustavia
$1,249 Roundtrip, found 4 days ago
$1,249
Roundtrip
found 4 days ago
Thu, Nov 26 - Sat, Dec 5
EWR
New York
SBH
Gustavia
$1,254 Roundtrip, found 4 days ago
$1,254
Roundtrip
found 4 days ago