Windward Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Windward vacation deals
- Tropical Hotel St Barth
Jan 10 - Jan 17Tropical Hotel St Barth + Flight
Saint-Jean6 nights5.0 star property9.8/10 - Exceptional (135 reviews)Roundtrip • Toronto (YTO) - St. Barthelemy (SBH)YYZ - SBH • 2 stops SBH - YYZ • 2 stopsCA $10,760CA $8,217found 1 day agoper traveller - Hotel Manapany
Jan 10 - Jan 17Hotel Manapany + Flight
Anse des Cayes6 nights5.0 star property9.4/10 - Exceptional (71 reviews)"Lovely, “barefoot chic” hotel that is top class in all respects"Reviewed April 27, 2026Roundtrip • Toronto (YTO) - St. Barthelemy (SBH)YYZ - SBH • 2 stops SBH - YYZ • 2 stopsCA $11,879CA $9,647found 1 day agoper traveller - Le Toiny Hôtel & Beach Club
Jan 10 - Jan 17Le Toiny Hôtel & Beach Club + Flight
Toiny6 nights5.0 star property9.8/10 - Exceptional (59 reviews)"My husband and I stayed here for our honeymoon and had the most beautiful villa! When we checked into our villa there was the most wonderful welcome gift and card. It was the perfect peaceful and quiet oasis to end our trip. We loved the shuttle that takes you down to their beach club and beach where you can have lunch and enjoy the ocean views. The beach was rocky so we didn’t swim, but there is a pool down by the beach as well. We absolutely loved that everything was Le Toiny branded. The..."Reviewed October 24, 2026Roundtrip • Toronto (YTO) - St. Barthelemy (SBH)YYZ - SBH • 2 stops SBH - YYZ • 2 stopsCA $17,422CA $14,256found 1 day agoper traveller - GYP SEA Saint Barth
Jan 16 - Jan 23GYP SEA Saint Barth + Flight
Colombier6 nights5.0 star property9.8/10 - Exceptional (105 reviews)Roundtrip • Montreal (YMQ) - St. Barthelemy (SBH)YUL - SBH • 2 stops SBH - YUL • 2 stopsCA $10,830CA $9,177found 5 hours agoper traveller - Christopher Hotel
Jan 10 - Jan 17Christopher Hotel + Flight
Pointe Milou6 nights5.0 star property9.6/10 - Exceptional (265 reviews)Roundtrip • Toronto (YTO) - St. Barthelemy (SBH)YYZ - SBH • 2 stops SBH - YYZ • 2 stopsCA $16,119CA $13,759found 1 day agoper traveller
What to do in Windward
High-Speed Ferry to St. Barths
Full-Day St Barth Private Charter Tour
Windward Hotel Deals
Hotel Les Ondines Sur La Plage
Hotel Les Ondines Sur La Plage
"My husband and I stayed here for our honeymoon and had the most beautiful villa! When we checked into our villa there was the most wonderful welcome gift and card. It was the perfect peaceful and quiet oasis to end our trip. We loved the shuttle that takes you down to their beach club and beach where you can have lunch and enjoy the ocean views. The beach was rocky so we didn’t swim, but there is a pool down by the beach as well. We absolutely loved that everything was Le Toiny branded. The...
"One of the best hotels that I stayed with my wife in the Caribbean."
"Excellent service!!"
"Lovely, “barefoot chic” hotel that is top class in all respects"
"Amazing hotel with wonderful staff."
Frequently Asked Questions
How much does a Windward vacation package cost?
Explore the best of Windward from as low as CA $8,217. 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.