Search Deals onWindward Vacation Packages
Windward Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Tropical Hotel St Barth
Price was $5,754, price is now $4,280 per person
$4,280
per person
Feb 24 - Feb 28
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) 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 $6,430, price is now $4,690 per person
$4,690
per person
Feb 24 - Feb 28
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) 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.
Christopher Hotel
Price was $5,938, price is now $4,662 per person
$4,662
per person
Feb 24 - Feb 28
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) 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.
Le Toiny Hôtel & Beach Club
Price was $7,896, price is now $6,347 per person
$6,347
per person
Feb 24 - Feb 28
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) 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.
GYP SEA Saint Barth
Price was $6,846, price is now $5,770 per person
$5,770
per person
Feb 24 - Feb 28
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) 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.
Le Barthélemy Hotel & Spa
Price was $7,447, price is now $6,381 per person
$6,381
per person
Mar 1 - Mar 5
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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.
Hotel Barrière Le Carl Gustaf St Barth
Lurin
Price was $9,311, price is now $8,369 per person
$8,369
per person
Feb 24 - Feb 28
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) 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 Shell Beach 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
Tropical Hotel St Barth
Les Hauts de Saint Jean St. Barthelemy
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. ...
Christopher Hotel
Pointe Milou, 9 St. Barthelemy
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 ...
Le Barthélemy Hotel & Spa
Baie de Grand Cul de Sac St. Barthelemy
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 ...
Save an average of 15% on thousands of hotels when you're signed in
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 ...
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 Toiny Hôtel & Beach Club
1 Rue du Toiny St. Barthelemy
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 ...
Le Sereno
Grand Cul de Sac BP 19 St. Barthelemy
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 ...
La Maison Fleur de Lune
Grande Saline St. Barthelemy France
Stay at this hotel in St. Barthelemy. Enjoy free WiFi, free parking, and 2 hot tubs. Popular attractions Gustavia Harbor and Saline Beach are located ...
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.
Tue, Mar 31 - Thu, Apr 2
JFK
John F. Kennedy Intl.
SBH
Gustaf III
$665 Roundtrip, found 5 hours ago
$665
Roundtrip
found 5 hours ago
Wed, Jul 15 - Wed, Jul 22
SJU
Luis Munoz Marin Intl.
SBH
Gustaf III
$986 Roundtrip, found 2 days ago
$986
Roundtrip
found 2 days ago
Thu, Apr 2 - Sun, Apr 5
EWR
Newark Liberty Intl. Airport
SBH
Gustaf III
$1,190 Roundtrip, found 5 hours ago
$1,190
Roundtrip
found 5 hours ago
Thu, Apr 2 - Sun, Apr 5
LGA
LaGuardia
SBH
Gustaf III
$2,683 Roundtrip, found 18 hours ago
$2,683
Roundtrip
found 18 hours ago
