Search Deals onWindward Vacation Packages
Windward Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Christopher Hotel
Pointe Milou
Price was $4,338, price is now $3,402 per person
$3,402
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Tropical Hotel St Barth
Saint-Jean
Price was $5,131, price is now $3,552 per person
$3,552
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $5,630, price is now $4,067 per person
$4,067
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
GYP SEA Saint Barth
Colombier
Price was $6,015, price is now $4,650 per person
$4,650
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 Toiny Hôtel & Beach Club
Toiny
Price was $6,928, price is now $5,365 per person
$5,365
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Fouquet's Saint-Barth
Lurin
Price was $8,993, price is now $7,629 per person
$7,629
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Le Barthélemy Hotel & Spa
Grand Cul-de-Sac
Price was $8,804, price is now $7,492 per person
$7,492
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
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
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 ...
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. ...
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 ...
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
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 ...
Amnios St Barth
Lagon de Grand-Cul-de Sac St. Barthelemy
Book a stay at this boutique hotel in St. Barthelemy. Enjoy free parking, breakfast (surcharge), and room service. Popular attractions Gustavia Harbor and Grand ...
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 Lorient Beach are located ...
Lil' Home
548 Route de Dévêt, Devet St. Barthelemy
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 ...
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, Dec 8 - Thu, Dec 10
SXM
Princess Juliana Intl.
SBH
Gustaf III
$513 Roundtrip, found 2 days ago
$513
Roundtrip
found 2 days ago
Tue, Dec 8 - Thu, Dec 10
JFK
John F. Kennedy Intl.
SBH
Gustaf III
$814 Roundtrip, found 1 day ago
$814
Roundtrip
found 1 day ago
Tue, Dec 8 - Fri, Dec 11
EWR
Newark Liberty Intl. Airport
SBH
Gustaf III
$1,130 Roundtrip, found 20 hours ago
$1,130
Roundtrip
found 20 hours ago
Sun, Nov 15 - Wed, Nov 18
MIA
Miami Intl.
SBH
Gustaf III
$1,210 Roundtrip, found 3 hours ago
$1,210
Roundtrip
found 3 hours ago
