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.
GYP SEA Saint Barth

GYP SEA Saint Barth

5 out of 5
Price was CA $4,172, price is now CA $3,367 per person
CA $3,367
per person
Jun 18 - Jun 24
found 23 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Gustavia (SBH)
9.8/10 Exceptional! (92 reviews)
Amazing experience 5 stars

Reviewed on Mar 2, 2026

Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Price was CA $7,488, price is now CA $5,010 per person
CA $5,010
per person
May 15 - May 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Gustavia (SBH)
9.8/10 Exceptional! (104 reviews)
immaculate all around

Reviewed on Apr 5, 2026

Le Toiny Hôtel & Beach Club

Le Toiny Hôtel & Beach Club

5 out of 5
Price was CA $7,807, price is now CA $5,597 per person
CA $5,597
per person
Jun 18 - Jun 24
found 23 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Gustavia (SBH)
9.8/10 Exceptional! (48 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

Christopher Hotel

Christopher Hotel

5 out of 5
Price was CA $5,645, price is now CA $4,421 per person
CA $4,421
per person
May 15 - May 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Gustavia (SBH)
9.6/10 Exceptional! (232 reviews)
Excellent service with a great location. Gladly return to this hotel.

Reviewed on Mar 14, 2026

Le Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa

5 out of 5
Price was CA $10,011, price is now CA $8,377 per person
CA $8,377
per person
May 15 - May 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Gustavia (SBH)
9.8/10 Exceptional! (85 reviews)
Everything there was amazing and the staff

Reviewed on Mar 6, 2026

Windward Hotel Deals

Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou, 9 St. Barthelemy
The price is CA $1,480 per night from Apr 13 to Apr 14
CA $1,480
CA $1,815 total
Apr 13 - Apr 14
includes taxes & fees
9.6/10 Exceptional! (234 reviews)
Excellent service with a great location. Gladly return to this hotel.

Reviewed on Mar 14, 2026

Christopher Hotel
Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Les Hauts de Saint Jean St. Barthelemy
The price is CA $1,161 per night from May 6 to May 7
CA $1,161
CA $1,219 total
May 6 - May 7
includes taxes & fees
9.8/10 Exceptional! (104 reviews)
immaculate all around

Reviewed on Apr 5, 2026

Tropical Hotel St Barth
Rosewood Le Guanahani St Barth

Rosewood Le Guanahani St Barth

Grand Cul De Sac St. Barthelemy
The price is CA $2,551 per night from May 6 to May 7
CA $2,551
CA $2,679 total
May 6 - May 7
includes taxes & fees
9.8/10 Exceptional! (62 reviews)
Fabulous hotel. The staff were incredible

Reviewed on Mar 20, 2026

Rosewood Le Guanahani St Barth
See all 2,360 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 $3,367. 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

Grand Cul de Sac

Grand Cul de Sac

3.5/5(5 reviews)

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
Gouverneur Beach

Gouverneur Beach

3/5(1 review)

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

Gouverneur Beach

What to do in Windward

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
High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

CA $103
per adult
80% of travellers recommend
High-Speed Ferry to St. Barths
Love Boat

Full-Day St Barth Private Charter Tour

CA $2,676
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.