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

Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou, 9 St. Barthelemy
The price is S$1,527 per night from 18 Dec to 19 Dec
S$1,527
18 Dec - 19 Dec
includes taxes & fees
9.4/10 Exceptional! (228 reviews)
We love the St Christopher. It has a beautiful location and very friendly staff!!

Reviewed on 3 Dec, 2025

Christopher Hotel
Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Les Hauts de Saint Jean St. Barthelemy
9.6/10 Exceptional! (95 reviews)
St Barth is one of the most perfect places on Earth, and this is the best place to stay there unless you can afford Eden Rock or Le Cheval Blanc.

Reviewed on 29 Nov, 2025

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Tropical Hotel St Barth
Le Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa

5 out of 5
Baie de Grand Cul de Sac St. Barthelemy
The price is S$3,490 per night from 9 Dec to 10 Dec
S$3,490
9 Dec - 10 Dec
includes taxes & fees
9.6/10 Exceptional! (79 reviews)
Wonderful Hotel ! Staff was very attentive, friendly, professional. Food was excellent. Can’t wait to return in the future.

Reviewed on 4 Jun, 2025

Le Barthélemy Hotel & Spa
See all 2,498 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$131
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$98
per adult
76% of travellers recommend
High-Speed Ferry to St. Barths
Love Boat

Full-Day St Barth Private Charter Tour

S$2,559
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.