Windward Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Charles Guerrero

Top hotels in Windward

Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Les Hauts de Saint Jean St. Barthelemy
9.6/10 Exceptional! (100 reviews)
Great location at St.Jean beach. Staff were very helpful and great to talk with. The rooms are very small we stayed in jungle room 3. No view or patio in room just in hall outside of room. Free breakfast. Overpriced for what is offered. 40 euros for taxi into town. We rented a car for 1 day that’s ...

Reviewed on 22 Jan 2026

Tropical Hotel St Barth
Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou, 9 St. Barthelemy
The price is 44.329.950 ₫ per night from 10 Mar to 11 Mar
44.329.950 ₫
51.454.954 ₫ total
10 Mar - 11 Mar
includes taxes & fees
9.4/10 Exceptional! (230 reviews)
Great rooms, service and amenities!

Reviewed on 19 Jan 2026

Christopher Hotel
Rosewood Le Guanahani St Barth

Rosewood Le Guanahani St Barth

Grand Cul De Sac St. Barthelemy
9.8/10 Exceptional! (60 reviews)
DID NOT GO TO SPA/ UPSET WE WERE NOT ABLE TO USE POOL ONE AFTERNOON DUE TO A CHILD WAS IN POOL WITHOUT ANY SWIM DIAPERS AND HAD AN ACCIDENT

Reviewed on 4 Nov 2025

Rosewood Le Guanahani St Barth
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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