Windward Vacation Packages

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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
Price was CA $7,210, price is now CA $5,608 per person
CA $5,608
per person
Oct 18 - Oct 24
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Gustavia (SBH)
9.8/10 Exceptional! (43 reviews)
It was perfect . It’s a beautiful property and the service was a dream. They thought about and catered to everything proactively.

Reviewed on Aug. 4, 2025

Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Price was CA $15,231, price is now CA $10,484 per person
CA $10,484
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Gustavia (SBH)
9.8/10 Exceptional! (92 reviews)
Expensive but it's St Barts as expected...this an amazing hotel.,loved the location, the views, the service,the rooms and Beeakfast was good as well..will definitely go back again.10/10

Reviewed on Jul. 31, 2025

GYP SEA Saint Barth

GYP SEA Saint Barth

5 out of 5
Price was CA $9,621, price is now CA $7,501 per person
CA $7,501
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Gustavia (SBH)
9.8/10 Exceptional! (83 reviews)
We loved this hotel, however there were no locks on the door of one of the bedrooms in our suite. The room could be accessed from the outside. The hotel is on a beautiful hilltop but, we couldn’t let our kids sleep in that room. The hotel had no way to rectify. The hotel and staff are amazing but that would be a consideration for not returning to the 3 bedroom suite.

Reviewed on Aug. 1, 2025

Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes
Price was CA $10,803, price is now CA $8,625 per person
CA $8,625
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Gustavia (SBH)
9.4/10 Exceptional! (66 reviews)
The property was exquisite. The entire staff was incredible, especially Noémie from Reception. She went above and beyond to make our 11th anniversary very memorable. I am already looking forward to a more extended visit to Hotel Manapany.

Reviewed on Jun. 15, 2025

Christopher Hotel

Christopher Hotel

5 out of 5
Price was CA $8,364, price is now CA $7,303 per person
CA $7,303
per person
Nov 23 - Nov 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Gustavia (SBH)
9.6/10 Exceptional! (225 reviews)
The property was beautiful, the staff was outstanding and excellent customer service. However, the room didn’t not get cool enough and they had to bring me a fan and the bathroom wooden shower door was rotted and chipping. The room needs to be updated.

Reviewed on Aug. 22, 2025

Windward Hotel Deals

Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou, 9, St. Barthelemy
Get rates
Christopher Hotel
Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Les Hauts de Saint Jean, St. Barthelemy
Get rates
Tropical Hotel St Barth
Rosewood Le Guanahani St Barth

Rosewood Le Guanahani St Barth

Grand Cul De Sac, St. Barthelemy
Get rates
Rosewood Le Guanahani St Barth
See all 2,327 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 $5,608. 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 $2,733
per traveller
Full-Day St Barth Private Charter Tour
High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

CA $103
per adult
76% of travellers recommend
High-Speed Ferry to St. Barths
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.