Windward Vacation Packages

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Windward Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Le Toiny Hôtel & Beach Club

Le Toiny Hôtel & Beach Club

5 out of 5
per person
Oct 19 - Oct 26
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Gustavia (SBH)
10/10 Exceptional! (38 reviews)
Super on the accommodations! Enjoyed the privacy and offered many extras! But, time to change the mattress, window blinds do not work and the grounds need a some attention. Other than that it was definitely a pleasant experience

Reviewed on Jun. 2, 2025

Windward Hotel Deals

Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou, 9, St. Barthelemy
The price is CA $1,150 per night from Jul 30 to Jul 31
CA $1,150
CA $1,466 total
Jul 30 - Jul 31
includes taxes & fees
9.4/10 Exceptional! (221 reviews)
Needs better or more thoughtful welcome gifts.
"For the cost, there could have been better welcome gifts, like a beach, tote bag. There was no bag at all, which is not on par with hotels in this range."

Reviewed on Jul. 4, 2025

Christopher Hotel
Rosewood Le Guanahani St Barth

Rosewood Le Guanahani St Barth

Grand Cul De Sac, St. Barthelemy
The price is CA $1,613 per night from Aug 3 to Aug 4
CA $1,613
CA $1,694 total
Aug 3 - Aug 4
includes taxes & fees
9.8/10 Exceptional! (51 reviews)
Excellent Stay
"Superior service."

Reviewed on May 14, 2025

Rosewood Le Guanahani St Barth
Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Les Hauts de Saint Jean, St. Barthelemy
The price is CA $898 per night from Jul 30 to Jul 31
CA $898
CA $943 total
Jul 30 - Jul 31
includes taxes & fees
9.6/10 Exceptional! (89 reviews)
"Excellent property, excellent service"

Reviewed on Jul. 14, 2025

Tropical Hotel St Barth
See all 2,376 properties in Windward
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Windward vacation package cost?
Explore the best of Windward from as low as CA $5,419. We offer a wonderful selection of rental cars, hotels and flights to suit every style and budget. Pick up even more discounts when you add a couple of tours or activities to your package.
How do I get a cheap travel package to Windward?
One of the simplest ways to save money (and time) is to combine your bookings with Expedia. Hotels, flights, rental cars and activities — we've got them all. Pick and choose a combination that suits you and see your savings stack up. Of course, a package deal is never a one-size-fits-all. That's why Expedia offers over 550 partner airlines and 1,000,000 hotel options around the globe, which lets you customize your Windward adventure.
How far in advance should I book my Windward vacation?
To score discount prices, book early. Airlines generally release flights, along with some of the lowest fares, around 12 months in advance. Hotels, activities and car rental should also be booked well in advance to avoid disappointment. If you're in need of a last-minute getaway to Windward, there are always lots of great deals on Expedia. Book your escape today!
What does an Expedia Windward travel package include?
Hotels, flights and a reliable car for all your road trip adventures. Simply pick and choose your favorite bundle and gain access to great discounts. Once you've made your booking, add on some activities and tours and watch your savings stack up. When it comes to planning your Windward vacation, the choice is all yours!
What should I know before booking a Windward travel package?
So many places to visit, so many things to do. With a travel package, you can check more of them off your list. Combine your flights, hotels and rental cars and score big savings.
Can I choose my airline with a Windward Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines throughout the world. Our packages give you the freedom to pick from available flights, hotels and activities that fit your needs.
If I'm not able to travel, can I cancel my Windward vacation package?
You can. We understand that things don't always go to plan, so we're here to help if you have to make changes to your Windward vacation package. You may be able to cancel or change your itinerary at no cost if you've booked in the last 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Visit our Customer Service Portal for more information. Also, check your itinerary for the finer details on change fees.

Discover the most popular places to visit in Windward

Gouverneur Beach

Gouverneur Beach

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

Gouverneur Beach

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

What to do in Windward

Plage de Saint-Jean

Full-Day St Barth Private Charter Tour

CA $2,717
per traveller
Full-Day St Barth Private Charter Tour
High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

CA $102
per adult
76% of travellers recommend
High-Speed Ferry to St. Barths
Panoramic view of vibrant St. Martin

Edge Ferry Tickets to St. Barts

CA $137
per adult
84% of travellers recommend
Edge Ferry Tickets to St. Barts
See all activities in Windward
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.