Leeward Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Top hotels in Leeward

GYP SEA Saint Barth
GYP SEA Saint Barth
5 out of 5
Le Colombier, St. Barthelemy
The price is S$1,398 per night from 3 Dec to 4 Dec
S$1,398
includes taxes & fees
3 Dec - 4 Dec
9.6/10 Exceptional! (53 reviews)
"Quiet, clean and beautiful. Staff friendly and very helpful. We very much enjoyed our stay."

Reviewed on 12 Aug,2024

GYP SEA Saint Barth
Hotel Barrière Le Carl Gustaf St Barth
Hotel Barrière Le Carl Gustaf St Barth
5 out of 5
Rue des Normands, Lieu Dit Lurin, St. Barthelemy, Leeward
The price is S$2,446 per night from 1 Dec to 2 Dec
S$2,446
includes taxes & fees
1 Dec - 2 Dec
9.6/10 Exceptional! (17 reviews)
"The Carl Gustaf is magical. A short walk ro Shellona beach or the hotel will drive you. The spa was spectacular. I had a massage & facial that were second to none. The view of the island is magnificent. The staff are lovely & helpful. The rooms are spacious w/coffee pods, drinks & munchies. A true ..."

Reviewed on 15 Nov,2024

Hotel Barrière Le Carl Gustaf St Barth
Pearl Beach Hotel
Pearl Beach Hotel
Plage De St. Jean BP1058, St. Barthelemy, French West Indies
The price is S$721 per night from 3 Dec to 4 Dec
S$721
includes taxes & fees
3 Dec - 4 Dec
9.2/10 Wonderful! (156 reviews)
"Perfect spot, beautiful beach and super friendly and helpful staff."

Reviewed on 21 Oct,2024

Pearl Beach Hotel
See all 1,668 properties in Leeward
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.

Popular places to visit

Corossol Beach

Why not spend a care-free afternoon at Corossol Beach during your travels in Gustavia? Amble around the area's marina or visit its shops.

Corossol Beach

What to do in Leeward

Panoramic view of vibrant St. Martin

Edge Ferry Tickets to St. Barts

S$134
Per adult
86% of travellers recommend
Edge Ferry Tickets to St. Barts
Lunch at Meads BAy

Ultimate Prickly Pear and Anguilla Experience

S$185
Per adult
82% of travellers recommend
Ultimate Prickly Pear and Anguilla Experience
St Maarten Island Private Group Whole Day Tour

St Maarten Island Private Group Tour

S$85
Per adult
100% of travellers recommend
St Maarten Island Private Group Tour
See all activities in Leeward

* 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.