Leeward Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Leeward
GYP SEA Saint Barth
Le Colombier St. Barthelemy
S$1,093
14 Aug - 15 Aug
includes taxes & fees
9.8/10 Exceptional! (101 reviews)
"Very quiet, nice property that allows relaxing and enjoyment of views of the island. Staff very helpful.. we got lost one night and the front desk staff stayed on the phone to guide us back. Any issue was attended to immediately."
Reviewed on 29 Jun, 2026
Fouquet's Saint-Barth
Rue des Normands, Lieu Dit Lurin St. Barthelemy Leeward
S$2,096
14 Aug - 15 Aug
includes taxes & fees
Pearl Beach Hotel
Plage De St. Jean BP1058 St. Barthelemy French West Indies
S$838
9 Aug - 10 Aug
includes taxes & fees
9.4/10 Exceptional! (204 reviews)
"I liked that it's beachfront, with direct access; the bathrooms need some TLC."
Reviewed on 31 Jul, 2026
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 Leeward holiday package cost?
The most affordable Leeward holiday package is , so the trip of your dreams can become a reality — without burning a hole in your pocket. Combine flights, hotels and car rentals to customize a package that matches your travelling style.
How do I get a cheap travel package to Leeward?
Crafting your own Leeward holiday package with Expedia is one of the best ways to save. We offer access to over 550 air carriers and 1,000,000 properties across the globe. With such an amazing range to select from, you'll have no trouble pulling together your perfect getaway.
How far in advance should I book my Leeward holiday?
Get rewarded with the widest variety and the cheapest prices by booking your Leeward adventure early. Air carriers generally release flight tickets around a year before departure, so reserve your spot as soon as you can. That said, Expedia is committed to giving you the best deals around, so it's always a good time to book your dream holiday!
What does an Expedia Leeward travel package include?
Hotels, flights and a shiny set of wheels for all your fun road trip adventures. Simply choose your favourite bundle and gain access to great discounts. Once you've made your booking, add on a couple of experiences and tours and watch your savings grow. When it comes to creating your Leeward escape, you're the one in control!
What should I know before booking a Leeward travel package?
A package can be easier on the bank balance than separately booking all you need for your trip. For example, combine your flights, hotels and rental cars and save a packet. No matter your holiday plans, there's bound to be a package that best suits your budget.
Can I choose my airline with a Leeward Expedia holiday package?
Yes, you're in control. We offer more than 550 partner airlines globally, so you can customize your Leeward holiday according to your needs and budget.
If I'm not able to travel, can I cancel my Leeward holiday package?
Don't worry if you're rethinking your Leeward holiday package — you can cancel or amend your booking. And if you've booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur fees from your airline, hotel or car rental company. We get that your circumstances can suddenly change, so look up our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.
What to do in Leeward
St Maarten Beach hopping tour (Oreint beach and Maho beach combo)
S$77
per adult
Billy Bones St.Maarten Getaway for CRUISE SHIP GUESTS
S$187
per adult
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line
S$174
per adult
90% of travellers recommend
* 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.
