Windward Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Charles Guerrero

Top hotels in Windward

Christopher Hotel

Christopher Hotel

Pointe Milou, 9 St. Barthelemy
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Christopher Hotel
Le Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa

Baie de Grand Cul de Sac St. Barthelemy
43.255.721 ₫
52.980.696 ₫ total
17 Aug - 18 Aug
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 20 Jun 2026

Le Barthélemy Hotel & Spa
Rosewood Le Guanahani St Barth

Rosewood Le Guanahani St Barth

Grand Cul De Sac St. Barthelemy
9.8/10 Exceptional! (74 reviews)
"Our experience at Rosewood Le Guanahani St. Barth was mixed. The property is beautiful, very well maintained, and in a stunning location. We encountered several friendly and helpful staff members, and the team was especially helpful with arranging taxis and transportation around the island. Unfortunately, ..."

Reviewed on 11 Aug 2026

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Rosewood Le Guanahani St Barth
See all 2,242 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 holiday 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 1null000null000 hotel options around the globe, which lets you customize your Windward adventure.
How far in advance should I book my Windward holiday?
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 favourite 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 holiday, 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 holiday 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 holiday 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 holiday 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.

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