Windward Holidays

Photo by Charles Guerrero

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 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

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! (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 17 Jan, 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 S$2,329 per night from 22 Feb to 23 Feb
S$2,329
22 Feb - 23 Feb
includes taxes & fees
9.4/10 Exceptional! (230 reviews)
Great rooms, service and amenities!

Reviewed on 19 Jan, 2026

Christopher Hotel
Le Sereno

Le Sereno

5 out of 5
Grand Cul de Sac BP 19 St. Barthelemy
The price is S$2,994 per night from 23 Jan to 24 Jan
S$2,994
23 Jan - 24 Jan
includes taxes & fees
9.6/10 Exceptional! (61 reviews)
Boutique hotel very nice quiet exclusive concierge service was top strongly recommend

Reviewed on 2 Mar, 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 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.

What to do in Windward

Panoramic view of vibrant St. Martin

Edge Ferry Tickets to St. Barts

S$129
per adult
84% of travellers recommend
Edge Ferry Tickets to St. Barts
High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

S$97
per adult
80% of travellers recommend
High-Speed Ferry to St. Barths
Love Boat

Full-Day St Barth Private Charter Tour

S$2,541
per traveller
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.