Windward Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Charles Guerrero

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Windward Vacation Deals

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 $9,714, price is now CA $7,007 per person
CA $7,007
per person
Apr 16 - Apr 23
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Gustavia (SBH)
9.8/10 Exceptional! (94 reviews)
The service was excellent - especially the concierge. The staff was friendly and always accommodating. The hotel was beautiful; room was spotless and comfortable. We enjoyed the breakfast thoroughly! Would recommend to everyone!

Reviewed on Feb 12, 2026

Le Toiny Hôtel & Beach Club

Le Toiny Hôtel & Beach Club

5 out of 5
Price was CA $19,316, price is now CA $14,879 per person
CA $14,879
per person
Apr 16 - Apr 23
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Gustavia (SBH)
9.8/10 Exceptional! (44 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

GYP SEA Saint Barth

GYP SEA Saint Barth

5 out of 5
Price was CA $9,923, price is now CA $8,244 per person
CA $8,244
per person
Apr 16 - Apr 23
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Gustavia (SBH)
9.8/10 Exceptional! (83 reviews)
Great service Amazing beach club

Reviewed on Nov 24, 2025

Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes
Price was CA $10,834, price is now CA $9,155 per person
CA $9,155
per person
Apr 16 - Apr 23
found 1 day ago
Roundtrip flight included
Montreal (YMQ) 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

Le Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa

5 out of 5
Price was CA $19,091, price is now CA $16,218 per person
CA $16,218
per person
Apr 16 - Apr 23
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Gustavia (SBH)
9.8/10 Exceptional! (77 reviews)
Staff-10/10 Food-10/10 Amenities-10/10 Only thing Le Barthelemy - wish they use cooling bedsheets. Or comforters - that are less warm.

Reviewed on Dec 15, 2025

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Windward Hotel Deals

Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Les Hauts de Saint Jean St. Barthelemy
The price is CA $1,411 per night from Feb 16 to Feb 17
CA $1,411
CA $1,482 total
Feb 16 - Feb 17
includes taxes & fees
9.6/10 Exceptional! (100 reviews)
Great location at St.Jean beach. Staff were very helpful and great to talk with. The rooms are very small we stayed in jungle room 3. No view or patio in room just in hall outside of room. Free breakfast. Overpriced for what is offered. 40 euros for taxi into town. We rented a car for 1 day that’s ...

Reviewed on Jan 22, 2026

Tropical Hotel St Barth
Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou, 9 St. Barthelemy
The price is CA $2,195 per night from Mar 9 to Mar 10
CA $2,195
CA $2,571 total
Mar 9 - Mar 10
includes taxes & fees
9.4/10 Exceptional! (230 reviews)
Great rooms, service and amenities!

Reviewed on Jan 19, 2026

Christopher Hotel
Rosewood Le Guanahani St Barth

Rosewood Le Guanahani St Barth

Grand Cul De Sac St. Barthelemy
9.8/10 Exceptional! (60 reviews)
DID NOT GO TO SPA/ UPSET WE WERE NOT ABLE TO USE POOL ONE AFTERNOON DUE TO A CHILD WAS IN POOL WITHOUT ANY SWIM DIAPERS AND HAD AN ACCIDENT

Reviewed on Nov 4, 2025

Get rates
Rosewood Le Guanahani St Barth
See all 2,318 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.
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Frequently asked questions

How much does a Windward vacation package cost?
Explore the best of Windward from as low as CA $7,007. 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 featuring general coastal views, a sandy beach and rocky coastline

Gouverneur Beach

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

Gouverneur Beach
The most beautiful place in the world

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

Panoramic view of vibrant St. Martin

Edge Ferry Tickets to St. Barts

CA $136
per adult
84% of travellers recommend
Edge Ferry Tickets to St. Barts
High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

CA $102
per adult
80% of travellers recommend
High-Speed Ferry to St. Barths
Love Boat

Full-Day St Barth Private Charter Tour

CA $2,740
per traveller
Full-Day St Barth Private Charter Tour
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.