Book Exclusive Windward Vacation Packages

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Windward flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes
Price was CA $7,024, price is now CA $6,199 per person
CA $6,199
per person
Nov 6 - Nov 9
found 20 hours ago
Roundtrip flight included
Montreal (YUL) 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

Le Toiny Hôtel & Beach Club

5 out of 5
Toiny
Price was CA $8,465, price is now CA $7,109 per person
CA $7,109
per person
Nov 6 - Nov 9
found 20 hours ago
Roundtrip flight included
Montreal (YUL) 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

Fouquet's Saint-Barth

5 out of 5
Lurin
Price was CA $16,344, price is now CA $14,366 per person
CA $14,366
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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.
Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou
Price was CA $7,749, price is now CA $7,566 per person
CA $7,566
per person
Nov 6 - Nov 9
found 20 hours ago
Roundtrip flight included
Montreal (YUL) 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 Windward hotels deals

Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou, 9 St. Barthelemy
Get rates
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.
Pool
Breakfast included
Le Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa

5 out of 5
Baie de Grand Cul de Sac St. Barthelemy
The price is CA $2,274 per night
CA $2,274
CA $2,791 total
Aug 15 - Aug 16
includes taxes & fees
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.
On private beach
Pool
Rosewood Le Guanahani St Barth

Rosewood Le Guanahani St Barth

Grand Cul De Sac St. Barthelemy
The price is CA $3,110 per night
CA $3,110
CA $3,265 total
Aug 15 - Aug 16
includes taxes & fees
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 are located nearby.
Pool
Breakfast included
Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Les Hauts de Saint Jean St. Barthelemy
Get rates
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.
Pool
Breakfast included
Le Toiny Hôtel & Beach Club

Le Toiny Hôtel & Beach Club

5 out of 5
1 Rue du Toiny St. Barthelemy
Get rates
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.
Pool
Breakfast included
Lil' Home

Lil' Home

548 Route de Dévêt, Devet St. Barthelemy
Get rates
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 located nearby.
Pool
Kitchen
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See all available properties in Windward
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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.

Photos of local treasures

Browse Windward vacation photos for more inspiration

A red boat on a sandy beach with a rocky hill in the background.
A beach with clear turquoise water, a rocky cliff, and a small island in the distance.
A beach with clear turquoise water, rocky cliffs, and sandy shores.
A coastal landscape with turquoise waters, palm trees, and a hilly background with buildings.
A coastal village with red-roofed buildings, clear turquoise waters, and a stone staircase leading up to the houses.

Frequently asked questions

How much are vacation packages to Windward?
With vacation packages on offer for only CA $6,199, you won't need to drain your bank balance to travel to Windward. Travelocity is here to help. Bundle up hotels, flights and experiences into a package and land excellent discounts. The more you book, the greater the savings.
Where can I get the best vacation package deals for Windward?
Walking away with an amazing package deal to Windward couldn't be easier with Travelocity. With 400 partner airlines and 1,000,000 properties worldwide, you'll have loads of choice when selecting your flights and hotels.
Why should I book my Windward vacation package with Travelocity?
Because you'll never wander on your own if you lock in your vacation with us, and we offer round-the-clock support and exceptional service to boot. Add to that our Price Match Guarantee and countless experiences and destinations to select from. We're here to help you jet off on the vacation of a lifetime.
Can I save on my Windward car rental if I bundle it with a hotel or flight?
Sure can. And our Windward vacation packages will help you do it. With just a few clicks you can save cash as well as time by booking everything in one place. Pick up the keys to your rental car then set your own course. Looking for things to do? Add some activities or experiences to your package and save on those too.
Which airport is best for Windward?
Princess Juliana Intl. Airport (SXM) is an excellent option for travelers hopping on a plane to Windward. Robert L. Bradshaw Intl. Airport (SKB) and Clayton J. Lloyd Intl. Airport (AXA) also welcome many flights to the region.