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 $11,089, price is now CA $7,368 per person
CA $7,368
per person
Dec 20 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) 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 $17,456, price is now CA $13,916 per person
CA $13,916
per person
Dec 20 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) 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 $12,480, price is now CA $9,978 per person
CA $9,978
per person
Dec 20 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) 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 Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa

5 out of 5
Grand Cul-de-Sac
Save 100% on your flight
Price was CA $19,747, price is now CA $16,749 per person
CA $16,749
per person
Jan 6 - Jan 10
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YUL) 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.
Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes
Price was CA $11,169, price is now CA $9,118 per person
CA $9,118
per person
Dec 13 - Dec 19
found 1 day 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.

Top Windward hotels deals

Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou, 9 St. Barthelemy
The price is CA $1,663 per night
CA $1,663
CA $2,000 total
Nov 29 - Nov 30
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.
Pool
Breakfast included
Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Les Hauts de Saint Jean St. Barthelemy
The price is CA $1,246 per night
CA $1,246
CA $1,309 total
Nov 16 - Nov 17
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.
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 $2,195 per night
CA $2,195
CA $2,591 total
Dec 13 - Dec 14
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.
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 $3,388 per night
CA $3,388
CA $3,955 total
Nov 16 - Nov 17
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
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.
Pool
Pet-friendly
Le Sereno

Le Sereno

5 out of 5
Grand Cul de Sac BP 19 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 Grand Cul de Sac are located nearby.
On private beach
Pool
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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 beach with clear turquoise water, palm trees, and boats.
A tropical beach with clear turquoise waters, a boat, and a resort with thatched-roof huts.
A coastal resort with clear turquoise waters, palm trees, and a beach with sun loungers.
A coastal landscape with turquoise waters, a rocky outcrop, and lush greenery.
A beach sign with 'Gouverneur' written on it, surrounded by trees and a sandy path.

Frequently asked questions

How much are vacation packages to Windward?
With vacation packages on offer for only CA $7,368, 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.