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 $4,200 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
Colombier
Price was CA $5,431, price is now CA $4,461 per person
CA $4,461
per person
Jul 11 - Jul 17
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Gustavia (SBH)
9.8/10 Exceptional! (95 reviews)
Wonderful hotel. I would definitely stay there again. If you prefer quiet and relaxing, this is the place.

Reviewed on May 7, 2026

Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Saint-Jean
Price was CA $6,401, price is now CA $4,590 per person
CA $4,590
per person
Jul 11 - Jul 17
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Gustavia (SBH)
9.8/10 Exceptional! (111 reviews)
Great and beautiful hotel, nice food, excellent location! Loved it

Reviewed on May 5, 2026

Le Toiny Hôtel & Beach Club

Le Toiny Hôtel & Beach Club

5 out of 5
Toiny
Price was CA $7,895, price is now CA $5,852 per person
CA $5,852
per person
Jul 11 - Jul 17
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Gustavia (SBH)
9.8/10 Exceptional! (50 reviews)
Spectacular property with a wonderful, attentive staff. Couldn’t have been a better stay!

Reviewed on May 3, 2026

Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou
Price was CA $5,646, price is now CA $4,532 per person
CA $4,532
per person
Jul 11 - Jul 17
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Gustavia (SBH)
9.6/10 Exceptional! (238 reviews)
Breakfast was outstanding every day! ALL the staff at the hotel were very professional, attentive to customers, efficient. Bedrooms are amazing, spacious with all great attention and practicability. Only drawbacks are the costs and quality/quantity of food provided for the diner meals (low quantity and TOO, TOO expensive for what you get in your plate!). Being a French establishment, it shouldn't be like that. People are eating once and then, they go shopping at SUPER-U - 10x cheaper. It would be better to try to keep your clients on-site for lunch and diners and therefore, charge less $$ (more realistic prices!). Thank you!

Reviewed on Apr 28, 2026

Le Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa

5 out of 5
Grand Cul-de-Sac
Price was CA $10,277, price is now CA $8,504 per person
CA $8,504
per person
Jul 11 - Jul 17
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Gustavia (SBH)
9.8/10 Exceptional! (87 reviews)
We had a fabulous stay from start to finish. All the staff were welcoming and attentive and the concierge service was super helpful with recommendations and organizing bookings for restaurants. The hotel had great amenities including the spa, and our beachfront suite was wonderful. Being able to swim out to see turtles in the lagoon was a real highlight for the whole family.

Reviewed on Apr 6, 2026

Windward Hotel Deals

Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou, 9 St. Barthelemy
The price is CA $1,093 per night from May 15 to May 16
CA $1,093
CA $1,409 total
May 15 - May 16
includes taxes & fees
9.6/10 Exceptional! (240 reviews)
Breakfast was outstanding every day! ALL the staff at the hotel were very professional, attentive to customers, efficient. Bedrooms are amazing, spacious with all great attention and practicability. Only drawbacks are the costs and quality/quantity of food provided for the diner meals (low quantity ...

Reviewed on Apr 28, 2026

Christopher Hotel
Rosewood Le Guanahani St Barth

Rosewood Le Guanahani St Barth

Grand Cul De Sac St. Barthelemy
The price is CA $2,321 per night from Jun 9 to Jun 10
CA $2,321
CA $2,437 total
Jun 9 - Jun 10
includes taxes & fees
9.8/10 Exceptional! (66 reviews)
The property was sprawling with individual villa type accommodations. Breakfasts were excellent. Service throughout the resort was excellent. Staff was friendly and eager to help in any way they could. Beach was a little disappointing because it had sargassom washing up every day. The resort did ...

Reviewed on May 7, 2026

Rosewood Le Guanahani St Barth
Le Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa

5 out of 5
Baie de Grand Cul de Sac St. Barthelemy
The price is CA $2,158 per night from Jun 9 to Jun 10
CA $2,158
CA $2,672 total
Jun 9 - Jun 10
includes taxes & fees
9.8/10 Exceptional! (87 reviews)
We had a fabulous stay from start to finish. All the staff were welcoming and attentive and the concierge service was super helpful with recommendations and organizing bookings for restaurants. The hotel had great amenities including the spa, and our beachfront suite was wonderful. Being able to ...

Reviewed on Apr 6, 2026

Le Barthélemy Hotel & Spa
See all 2,344 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
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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 $4,461. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.