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 $5,053, price is now CA $4,704 per person
CA $4,704
per person
May 28 - Jun 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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
Price was CA $7,722, price is now CA $6,442 per person
CA $6,442
per person
May 28 - Jun 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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.
Christopher Hotel

Christopher Hotel

5 out of 5
Price was CA $5,858, price is now CA $5,327 per person
CA $5,327
per person
Jun 6 - Jun 13
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 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
The price is CA $1,404 per night
CA $1,404
CA $1,733 total
Apr 13 - Apr 14
includes taxes & fees
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

Tropical Hotel St Barth

5 out of 5
Les Hauts de Saint Jean St. Barthelemy
The price is CA $3,851 per night
CA $3,851
CA $4,044 total
Mar 20 - Mar 21
includes taxes & fees
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.
Rosewood Le Guanahani St Barth

Rosewood Le Guanahani St Barth

Grand Cul De Sac St. Barthelemy
The price is CA $2,607 per night
CA $2,607
CA $2,737 total
Apr 17 - Apr 18
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.
Amnios St Barth

Amnios St Barth

Lagon de Grand-Cul-de Sac St. Barthelemy
Get rates
Book a stay at this boutique hotel in St. Barthelemy. Enjoy free parking, breakfast (surcharge), and room service. Popular attractions Gustavia Harbor and Grand Cul de Sac are located nearby.
Le Toiny Hôtel & Beach Club

Le Toiny Hôtel & Beach Club

5 out of 5
1 Rue du Toiny St. Barthelemy
The price is CA $4,435 per night
CA $4,435
CA $4,657 total
Mar 26 - Mar 27
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 Petit Cul de Sac Beach are located nearby.
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.
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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 showing a sandy beach and general coastal views

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
The most beautiful place in the world

Grand Cul de Sac

Why not spend a carefree afternoon at Grand Cul de Sac during your travels in Anse du Grand Cul-de-Sac?

Grand Cul de Sac
Contrasts.

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

Contrasts.
Great place to relax after completing the route from "Going am wilden Kaiser".
The near end of the beach. So beautiful, and in the off-season, wonderfully quiet.
The most beautiful place in the world
Lazy day on the beach. (06.12.14) #travelbug #plagestjean #stbarths

Frequently asked questions

How much are vacation packages to Windward?
With vacation packages on offer for only CA $4,704, 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.