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 $9,727, price is now CA $7,357 per person
CA $7,357
per person
Jan 20 - Jan 27
found 19 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) 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
Price was CA $20,428, price is now CA $14,902 per person
CA $14,902
per person
Feb 21 - Feb 28
found 17 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) 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.
Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes
Price was CA $13,275, price is now CA $9,891 per person
CA $9,891
per person
Feb 21 - Feb 28
found 17 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) 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.
Christopher Hotel

Christopher Hotel

5 out of 5
Price was CA $10,934, price is now CA $8,465 per person
CA $8,465
per person
Feb 21 - Feb 28
found 17 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) 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.
GYP SEA Saint Barth

GYP SEA Saint Barth

5 out of 5
Price was CA $11,971, price is now CA $9,271 per person
CA $9,271
per person
Jan 24 - Jan 31
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.

Top Windward hotels deals

Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou, 9 St. Barthelemy
The price is CA $2,394 per night
CA $2,394
CA $2,791 total
Jan 11 - Jan 12, 2026
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 $3,607 per night
CA $3,607
CA $3,787 total
Jan 5 - Jan 6, 2026
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 Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa

5 out of 5
Baie de Grand Cul de Sac St. Barthelemy
The price is CA $3,049 per night
CA $3,049
CA $3,612 total
Dec 19 - Dec 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.
On private beach
Pool
Rosewood Le Guanahani St Barth

Rosewood Le Guanahani St Barth

Grand Cul De Sac St. Barthelemy
Get rates
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
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 breakfast, free parking, and a free airport shuttle. Popular attractions Gustavia Harbor and Grand Cul de Sac 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 $4,278 per night
CA $4,278
CA $4,492 total
Dec 20 - Dec 21
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
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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

Gouverneur Beach

Gouverneur Beach

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

Gouverneur Beach
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
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 $7,357, 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.