Leeward Vacations & Trips

Book a Hotel + Flight or Car together to unlock savings

Photo by Charles Guerrero

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥45,448 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

Leeward Hotel Deals

Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes St. Barthelemy
The price is ￥180,789 per night from Apr 27 to Apr 28
￥180,789
￥198,285 total
Apr 27 - Apr 28
includes taxes & fees
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 Mar 16, 2026

Hotel Manapany
Reve de Saint Barth

Reve de Saint Barth

Les Hauts de Flamands, Merlette St. Barthelemy
9.8/10 Exceptional! (59 reviews)
Excellent stay.

Reviewed on Mar 22, 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
9.4/10 Exceptional! (192 reviews)
Place had cacoroche and lots of noises from 3am - 5am from there kitchen was unable to get any sleep.

Reviewed on Mar 27, 2026

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Pearl Beach Hotel
See all 1,462 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 vacation package cost?
The most affordable Leeward vacation 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 traveling style.
How do I get a cheap travel package to Leeward?
Crafting your own Leeward vacation 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 vacation?
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 vacation!
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 favorite 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 vacation plans, there's bound to be a package that best suits your budget.
Can I choose my airline with a Leeward Expedia vacation package?
Yes, you're in control. We offer more than 550 partner airlines globally, so you can customize your Leeward vacation according to your needs and budget.
If I'm not able to travel, can I cancel my Leeward vacation package?
Don't worry if you're rethinking your Leeward vacation 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

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

￥8,731
per adult
94% of travellers recommend
St-Martin and St Maarten: Sightseeing Tour of the French and Dutch Sides of the Island
St Maarten Speed Boat

Speed Boat & Snorkeling Tour Pinel & Tintamarre Islands for CRUISE SHIP GUESTS

￥21,671
per adult
80% of travellers recommend
Speed Boat & Snorkeling Tour Pinel & Tintamarre Islands for CRUISE SHIP GUESTS
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

￥24,790
per adult
90% of travellers recommend
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line
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.