Windward Vacations & Trips

Book a Hotel + Flight or Car together to unlock savings

Photo by Charles Guerrero

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥45,448 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

Windward Hotel Deals

Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Les Hauts de Saint Jean St. Barthelemy
9.6/10 Exceptional! (99 reviews)
Great hotel! This is our second year in a row coming and it continues to get better every time. The staff is so warm and welcoming. Whether assisting with reservations on the island or helping you get a steamer the staff is quick and attentive. The food here is so underrated!! The burger was excellent. ...

Reviewed on Jan 17, 2026

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Tropical Hotel St Barth
Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou, 9 St. Barthelemy
The price is ￥243,264 per night from Feb 22 to Feb 23
￥243,264
￥286,230 total
Feb 22 - Feb 23
includes taxes & fees
9.4/10 Exceptional! (229 reviews)
Best service on the island, incredibly beautiful property. Delicious food.

Reviewed on Dec 31, 2025

Christopher Hotel
Le Sereno

Le Sereno

5 out of 5
Grand Cul de Sac BP 19 St. Barthelemy
The price is ￥351,498 per night from Jan 24 to Jan 25
￥351,498
￥369,073 total
Jan 24 - Jan 25
includes taxes & fees
9.6/10 Exceptional! (61 reviews)
Boutique hotel very nice quiet exclusive concierge service was top strongly recommend

Reviewed on Mar 2, 2025

Le Sereno
See all 2,326 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.

Frequently asked questions

How much does a Windward vacation package cost?
Explore the best of Windward from as low as . 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

￥11,743
per adult
80% of travellers recommend
High-Speed Ferry to St. Barths
Panoramic view of vibrant St. Martin

Edge Ferry Tickets to St. Barts

￥15,657
per adult
84% of travellers recommend
Edge Ferry Tickets to St. Barts
Love Boat

Full-Day St Barth Private Charter Tour

￥313,324
per traveler
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.