Leeward Holidays

Photo by Charles Guerrero

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    Save up to €185 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top hotels in Leeward

Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes St. Barthelemy
9.4/10 Exceptional! (69 reviews)
365 degrees of beauty the eye wanders off to more and more beauty! The staff is excellent, kind and so so lovely! The concierge took care of our every need! We’re definitely going to stay again!

Reviewed on 16 Mar 2026

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Hotel Manapany
Reve de Saint Barth

Reve de Saint Barth

Les Hauts de Flamands, Merlette St. Barthelemy
9.8/10 Exceptional! (57 reviews)
Many parking spaces to use if you rent a car which we did. The pictures are spot on for the aesthetics of the villa. Very modern which is a must for us when traveling. Indoor outdoor pool looks nice although we were out most of time so didn’t use it. Villa was very clean and had daily room ...

Reviewed on 16 Mar 2026

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Reve de Saint Barth
Pearl Beach Hotel

Pearl Beach Hotel

Plage De St. Jean BP1058 St. Barthelemy French West Indies
The price is €856 per night from 18 Mar to 19 Mar
€856
18 Mar - 19 Mar
includes taxes & fees
9.4/10 Exceptional! (191 reviews)
Too close to Airport

Reviewed on 31 Jan 2026

Pearl Beach Hotel
See all 1,459 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

Colombier Beach which includes landscape views, a bay or harbor and general coastal views

Colombier Beach

If a restful holiday is part of your travel plans, Colombier Beach might be the perfect place to visit during your trip to Colombier.

Colombier Beach

What to do in Leeward

St-Martin and St Maarten: Sightseeing Tour of the French and Dutch Sides of the Island

St-Martin and St Maarten: Sightseeing Tour of the French and Dutch Sides of the Island

€48
per adult
94% of travellers recommend
St-Martin and St Maarten: Sightseeing Tour of the French and Dutch Sides of the Island
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

€137
per adult
90% of travellers recommend
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line
St. Maarten Maho Beach Tour

St. Maarten Maho Beach Tour

€34
per adult
80% of travellers recommend
St. Maarten Maho Beach 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.