Windward Holidays

Photo by Charles Guerrero

  • Plan, book, travel with confidence

  • Better together

    Save up to S$600 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$1,233 per night from 12 May to 13 May
S$1,233
12 May - 13 May
includes taxes & fees
9.6/10 Exceptional! (236 reviews)
Staff super friendly. Pool could be a touch warmer

Reviewed on 7 Apr, 2026

Christopher Hotel
Le Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa

5 out of 5
Baie de Grand Cul de Sac St. Barthelemy
The price is S$2,537 per night from 11 May to 12 May
S$2,537
11 May - 12 May
includes taxes & fees
9.8/10 Exceptional! (87 reviews)
We had a fabulous stay from start to finish. All the staff were welcoming and attentive and the concierge service was super helpful with recommendations and organizing bookings for restaurants. The hotel had great amenities including the spa, and our beachfront suite was wonderful. Being able to ...

Reviewed on 6 Apr, 2026

Le Barthélemy Hotel & Spa
Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Les Hauts de Saint Jean St. Barthelemy
The price is S$962 per night from 25 May to 26 May
S$962
25 May - 26 May
includes taxes & fees
9.8/10 Exceptional! (107 reviews)
immaculate all around

Reviewed on 5 Apr, 2026

Tropical Hotel St Barth
See all 2,342 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

Love Boat

Full-Day St Barth Private Charter Tour

S$2,550
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.