Vacation Packages to Windward for 2025
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 $7,565, price is now $5,808 per person
$5,808
per person
Nov 1 - Nov 9
found 1 day ago
Roundtrip flight included
New York (NYC) 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.
GYP SEA Saint Barth
Save 100% on your flight
Price was $13,583, price is now $11,504 per person
$11,504
per person
Nov 1 - Nov 9
found 1 day ago
Roundtrip flight included
New York (NYC) 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 Toiny Hôtel & Beach Club
Price was $11,061, price is now $10,537 per person
$10,537
per person
Nov 1 - Nov 9
found 1 day ago
Roundtrip flight included
New York (NYC) 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.
Le Barthélemy Hotel & Spa
Price was $8,472, price is now $8,087 per person
$8,087
per person
Nov 1 - Nov 9
found 1 day ago
Roundtrip flight included
New York (NYC) 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.
Hotel Barrière Le Carl Gustaf St Barth
Lurin
Price was $14,171, price is now $14,171 per person
$14,171
per person
Nov 1 - Nov 9
found 1 day ago
Roundtrip flight included
New York (NYC) 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.
Top Hotel Deals
Christopher Hotel
Pointe Milou, 9, St. Barthelemy
1.7 km from city center
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
2.08 km from city center
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 ...
Tropical Hotel St Barth
Les Hauts de Saint Jean, St. Barthelemy
1.94 km from city center
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 ...
Le Toiny Hôtel & Beach Club
1 Rue du Toiny, St. Barthelemy
2.13 km from city center
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 ...
Le Barthélemy Hotel & Spa
Baie de Grand Cul de Sac, St. Barthelemy
1.86 km from city center
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 ...
Hotel Villa Lodge 4 épices
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 breakfast, free parking, and a free airport shuttle. Popular attractions Gustavia Harbor and ...
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.