Book Exclusive Windward Vacation Packages

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Windward flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Price was CA $8,828, price is now CA $5,935 per person
CA $5,935
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Gustavia (SBH)
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 condition in our reviews. Popular attractions Gustavia Harbor and St. Jean Beach are located nearby.
Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes
Price was CA $8,862, price is now CA $7,431 per person
CA $7,431
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip flight included
Montreal (YUL) 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.
Le Toiny Hôtel & Beach Club

Le Toiny Hôtel & Beach Club

5 out of 5
Price was CA $12,997, price is now CA $9,541 per person
CA $9,541
per person
Nov 9 - Nov 15
found 1 day ago
Roundtrip flight included
Montreal (YUL) 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.
GYP SEA Saint Barth

GYP SEA Saint Barth

5 out of 5
Price was CA $9,647, price is now CA $7,452 per person
CA $7,452
per person
Dec 3 - Dec 9
found 1 day ago
Roundtrip flight included
Montreal (YUL) 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.
Hotel Barrière Le Carl Gustaf St Barth

Hotel Barrière Le Carl Gustaf St Barth

5 out of 5
Lurin
Price was CA $63,458, price is now CA $54,862 per person
CA $54,862
per person
Dec 3 - Dec 9
found 1 day ago
Roundtrip flight included
Montreal (YUL) 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 Windward hotels deals

Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou, 9, St. Barthelemy
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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 attractions Gustavia Harbor and Marigot Beach are located nearby.
Pool
Breakfast included
Rosewood Le Guanahani St Barth

Rosewood Le Guanahani St Barth

Grand Cul De Sac, St. Barthelemy
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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 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
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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 condition 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
The price is CA $1,455 per night
CA $1,455
CA $1,528 total
Oct 15 - Oct 16
includes taxes & fees
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.
Pool
Breakfast included
Le Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa

5 out of 5
Baie de Grand Cul de Sac, St. Barthelemy
Get rates
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.
On private beach
Pool
Hotel Villa Lodge 4 épices

Hotel Villa Lodge 4 épices

Lagon de Grand-Cul-de Sac, St. Barthelemy
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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 Grand Cul de Sac are located nearby.
Pool
Breakfast included
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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.

Popular places to visit

Lorient Beach

Lorient Beach

Why not spend a carefree afternoon at Lorient Beach during your travels in Quartier Lorient? You can enjoy the restaurants while in the area.

Lorient Beach
Gouverneur Beach

Gouverneur Beach

Why not spend a carefree afternoon at Gouverneur Beach during your travels in Anse du Gouverneur?

Gouverneur Beach
Saline Beach

Saline Beach

Why not spend a carefree afternoon at Saline Beach during your travels in Morne Rouge?

Saline Beach

Photos of local treasures

Browse Windward vacation photos for more inspiration

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Frequently asked questions

How much are vacation packages to Windward?
With vacation packages on offer for only CA $5,935, 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.