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
Saint-Jean
Price was CA $5,549, price is now CA $4,094 per person
CA $4,094
per person
Jul 13 - Jul 18
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 valet parking. Our guests praise the helpful staff in our reviews. Popular attractions Gustavia Harbor and St. Jean Beach are located nearby.
Le Toiny Hôtel & Beach Club

Le Toiny Hôtel & Beach Club

5 out of 5
Toiny
Price was CA $7,743, price is now CA $5,513 per person
CA $5,513
per person
Jul 13 - Jul 18
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.
GYP SEA Saint Barth

GYP SEA Saint Barth

5 out of 5
Colombier
Price was CA $5,301, price is now CA $4,376 per person
CA $4,376
per person
Jul 13 - Jul 18
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 valet parking. Popular attractions Gustavia Harbor and Flamands Beach are located nearby.
Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou
Price was CA $4,995, price is now CA $4,127 per person
CA $4,127
per person
Jul 13 - Jul 18
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. Our guests praise the helpful staff in our reviews. Popular attractions Gustavia Harbor and Marigot Beach are located nearby.
Le Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa

5 out of 5
Grand Cul-de-Sac
Price was CA $8,766, price is now CA $7,327 per person
CA $7,327
per person
Jul 13 - Jul 18
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 valet parking. Popular attractions Gustavia Harbor and Grand Cul de Sac are located nearby.

Top Windward hotels deals

Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou, 9 St. Barthelemy
The price is CA $1,132 per night
CA $1,132
CA $1,450 total
Jun 1 - Jun 2
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.
Rosewood Le Guanahani St Barth

Rosewood Le Guanahani St Barth

Grand Cul De Sac St. Barthelemy
The price is CA $2,590 per night
CA $2,590
CA $2,719 total
Jun 1 - Jun 2
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.
Le Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa

5 out of 5
Baie de Grand Cul de Sac St. Barthelemy
The price is CA $2,162 per night
CA $2,162
CA $2,672 total
May 19 - May 20
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.
Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Les Hauts de Saint Jean St. Barthelemy
The price is CA $1,046 per night
CA $1,046
CA $1,098 total
Jun 10 - Jun 11
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.
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 $1,766 per night
CA $1,766
CA $1,855 total
Jun 7 - Jun 8
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.
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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.

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Frequently asked questions

How much are vacation packages to Windward?
With vacation packages on offer for only CA $4,094, 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.