Leeward Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Save up to CA $775 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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Leeward Hotel Deals

GYP SEA Saint Barth
GYP SEA Saint Barth
5 out of 5
Le Colombier, St. Barthelemy
The price is CA $699 per night from Jun. 18 to Jun. 19
CA $699
CA $734 total
includes taxes & fees
Jun 18 - Jun 19
9.6/10 Exceptional! (48 reviews)
"Arrived here for an overnight for a 50th bday for my gf…the place was so amazing we stayed a 2nd night and can’t wait for return! The staff, the setting, the accommodations were just off the charts..from the hotel to the Beach club, this pace is a 10"

Reviewed on Apr. 30, 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 CA $1,320 per night from Jun. 18 to Jun. 19
CA $1,320
CA $1,386 total
includes taxes & fees
Jun 18 - Jun 19
9.4/10 Exceptional! (9 reviews)
"The rooms were beautiful. The location was great - the housekeeping however is an issue. The front desk is very nice and goes out of their way to help."

Reviewed on Apr. 29, 2024

Hotel Barrière Le Carl Gustaf St Barth
Hotel Manapany
Hotel Manapany
5 out of 5
Anse des Cayes, St. Barthelemy
The price is CA $1,220 per night from Jun. 19 to Jun. 20
CA $1,220
CA $1,332 total
includes taxes & fees
Jun 19 - Jun 20
9.4/10 Exceptional! (58 reviews)
Great romantic getaway
"We had an incredible 4 night stay here. The staff was amazing especially Victor (the concierge) who went above and beyond and really made the trip special for us. I would highly recommend staying here."

Reviewed on Apr. 1, 2024

Hotel Manapany
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.

Discover the most popular places to visit in Leeward

What to do in Leeward

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.