Leeward Vacations & Trips

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Leeward Hotel Deals

GYP SEA Saint Barth

GYP SEA Saint Barth

5 out of 5
Le Colombier, St. Barthelemy
The price is ￥153,450 per night from Nov 10 to Nov 11
￥153,450
￥161,123 total
Nov 10 - Nov 11
includes taxes & fees
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

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 ￥293,128 per night from Nov 2 to Nov 3
￥293,128
￥307,784 total
Nov 2 - Nov 3
includes taxes & fees
9.6/10 Exceptional! (26 reviews)
A superb hotel in Gustavia with easy access to beach and dining

Reviewed on Aug 2, 2025

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 ￥140,838 per night from Nov 9 to Nov 10
￥140,838
￥147,880 total
Nov 9 - Nov 10
includes taxes & fees
9.2/10 Wonderful! (185 reviews)
The staff here was amazing. When we went to the airport, my girlfriend actually left a dress in our room. The staff grab the dress drove to the airport and gave us the address while we were waiting for our flight about to board! The restaurant here was incredible. The lobster was absolutely amazing. ...

Reviewed on Oct 7, 2025

Pearl Beach Hotel
See all 1,532 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

5 Hour Luxury Catamaran Day Sail in Sint Maarten on The Phoenix

5 Hour Luxury Catamaran Day Sail in Sint Maarten on The Phoenix

￥21,102
per adult
100% of travellers recommend
5 Hour Luxury Catamaran Day Sail in Sint Maarten on The Phoenix
St Maarten Speed Boat

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

￥21,102
per adult
74% of travellers recommend
Speed Boat & Snorkeling Tour Pinel & Tintamarre Islands for CRUISE SHIP GUESTS
Lunch at Meads BAy

Ultimate Prickly Pear and Anguilla Experience

￥22,620
per adult
82% of travellers recommend
Ultimate Prickly Pear and Anguilla Experience
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.