Windward Holidays

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    Save up to €185 when you book a flight and hotel together*
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Top hotels in Windward

Christopher Hotel
Christopher Hotel
5 out of 5
Pointe Milou, 9, St. Barthelemy
The price is €958 per night from 15 Jul to 16 Jul
€958
15 Jul - 16 Jul
includes taxes & fees
9.4/10 Exceptional! (220 reviews)
Needs better or more thoughtful welcome gifts.
"For the cost, there could have been better welcome gifts, like a beach, tote bag. There was no bag at all, which is not on par with hotels in this range."

Reviewed on 4 Jul 2025

Christopher Hotel
Rosewood Le Guanahani St Barth
Rosewood Le Guanahani St Barth
Grand Cul De Sac, St. Barthelemy
The price is €929 per night from 16 Jul to 17 Jul
€929
16 Jul - 17 Jul
includes taxes & fees
9.8/10 Exceptional! (50 reviews)
Excellent Stay
"Superior service."

Reviewed on 14 May 2025

Rosewood Le Guanahani St Barth
Tropical Hotel St Barth
Tropical Hotel St Barth
5 out of 5
Les Hauts de Saint Jean, St. Barthelemy
9.6/10 Exceptional! (87 reviews)
Perfect in parad
"Such a beautiful property and excellent service. From the courteous shuttle to and from the airport to the perfectly appointed rooms, it was a treat. 3 min walk to the beach, 5 min drive to the harbor for restaurants and shopping. Would highly recommend"

Reviewed on 10 Jul 2025

Get rates
Tropical Hotel St Barth
See all 2,586 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 1,000,000 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.

Popular places to visit

Saline Beach

Saline Beach

3/5(1 review)

Why not spend a care-free afternoon at Saline Beach during your travels in Morne Rouge?

Saline Beach

What to do in Windward

Plage de Saint-Jean

Full-Day St Barth Private Charter Tour

€1,700
per traveller
Full-Day St Barth Private Charter Tour
High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

€64
per adult
76% of travellers recommend
High-Speed Ferry to St. Barths
Panoramic view of vibrant St. Martin

Edge Ferry Tickets to St. Barts

€85
per adult
84% of travellers recommend
Edge Ferry Tickets to St. Barts
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.