Leeward Vacations & Trips

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

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    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit

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

    Plan, book, and manage your trip all in one place

Leeward Hotel Deals

GYP SEA Saint Barth

GYP SEA Saint Barth

5 out of 5
Le Colombier, St. Barthelemy
9.6/10 Exceptional! (83 reviews)
"We loved this hotel, however there were no locks on the door of one of the bedrooms in our suite. The room could be accessed from the outside. The hotel is on a beautiful hilltop but, we couldn’t let our kids sleep in that room. The hotel had no way to rectify. The hotel and staff are amazing but ..."

Reviewed on Aug 1, 2025

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GYP SEA Saint Barth
Reve de Saint Barth

Reve de Saint Barth

Les Hauts de Flamands, Merlette, St. Barthelemy
The price is ₩641,422 per night from Sep 29 to Sep 30
₩641,422
₩673,493 total
Sep 29 - Sep 30
includes taxes & fees
9.8/10 Exceptional! (47 reviews)
"This place is beautifully appointed , quiet and just idyllic , if I'm ever lucky enough to come to St Barts again I will stay here , also Constantine was really helpful and nothing was an issue , love this place Henry UK"

Reviewed on Sep 20, 2025

Reve de Saint Barth
Pearl Beach Hotel

Pearl Beach Hotel

Plage De St. Jean BP1058, St. Barthelemy, French West Indies
The price is ₩801,778 per night from Sep 29 to Sep 30
₩801,778
₩841,867 total
Sep 29 - Sep 30
includes taxes & fees
9.2/10 Wonderful! (182 reviews)
"We had a wonderful time! The food and service were excellent! We will definitely return again in the future!"

Reviewed on Sep 2, 2025

Pearl Beach Hotel
See all 1,412 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.