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.
Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Saint-Jean
Price was CA $8,431, price is now CA $6,387 per person
CA $6,387
per person
Aug 7 - Aug 14
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Gustavia (SBH)
9.8/10 Exceptional! (121 reviews)
Great location. Nice staff!

Reviewed on Jun 21, 2026

Le Toiny Hôtel & Beach Club

Le Toiny Hôtel & Beach Club

5 out of 5
Toiny
Price was CA $8,493, price is now CA $6,923 per person
CA $6,923
per person
Aug 9 - Aug 17
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Gustavia (SBH)
9.8/10 Exceptional! (51 reviews)
Property is beautiful. The staff is very courteous. The concierge was excellent with restaurant and site seeing suggestions. Truly enjoyed our stay.

Reviewed on Jun 8, 2026

Fouquet's Saint-Barth

Fouquet's Saint-Barth

5 out of 5
Lurin
Price was CA $11,399, price is now CA $10,122 per person
CA $10,122
per person
Aug 7 - Aug 14
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Gustavia (SBH)
9.8/10 Exceptional! (35 reviews)
Great location, luxury and very comfortable room with great terrace and best view in St Barts. Will be back!

Reviewed on May 25, 2026

Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes
Price was CA $7,477, price is now CA $6,938 per person
CA $6,938
per person
Jul 27 - Jul 31
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Gustavia (SBH)
9.4/10 Exceptional! (71 reviews)
365 degrees of beauty the eye wanders off to more and more beauty! The staff is excellent, kind and so so lovely! The concierge took care of our every need! We’re definitely going to stay again!

Reviewed on Mar 16, 2026

Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou
Price was CA $7,287, price is now CA $6,842 per person
CA $6,842
per person
Aug 7 - Aug 14
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Gustavia (SBH)
9.6/10 Exceptional! (245 reviews)
Awesome property , peaceful and beautiful views

Reviewed on Jun 5, 2026

Windward Hotel Deals

Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou, 9 St. Barthelemy
The price is CA $976 per night from Jul 14 to Jul 15
CA $976
CA $1,284 total
Jul 14 - Jul 15
includes taxes & fees
Christopher Hotel
Rosewood Le Guanahani St Barth

Rosewood Le Guanahani St Barth

Grand Cul De Sac St. Barthelemy
The price is CA $3,096 per night from Jun 29 to Jun 30
CA $3,096
CA $3,251 total
Jun 29 - Jun 30
includes taxes & fees
9.8/10 Exceptional! (68 reviews)
"Great breakfast, great staff, pretty room. The beach is ok. There’s a hike on property that is a leisurely beautiful hike."

Reviewed on Jun 4, 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 $2,380 per night from Jul 28 to Jul 29
CA $2,380
CA $2,905 total
Jul 28 - Jul 29
includes taxes & fees
9.8/10 Exceptional! (90 reviews)
"My wife and I travel extensively, and we both agreed: Le Barthélemy has the absolute best service of any hotel we have ever visited. It is a true 6-star experience. The staff genuinely cares and goes out of their way for everything—whether it’s arranging a midnight taxi across the island or preparing ..."

Reviewed on Jun 20, 2026

Le Barthélemy Hotel & Spa
See all 2,303 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 $6,387. 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.

What to do in Windward

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 $2,738
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.