Leeward Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Leeward Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Leeward Hotel Deals
Fouquet's Saint-Barth
Rue des Normands, Lieu Dit Lurin St. Barthelemy Leeward
CA $2,807
CA $2,947 total
Oct 29 - Oct 30
includes taxes & fees
9.6/10 Exceptional! (38 reviews)
"Amazing hotel with wonderful staff."
Reviewed on Aug 17, 2026
Hotel Manapany
Anse des Cayes St. Barthelemy
CA $2,091
CA $2,281 total
Nov 4 - Nov 5
includes taxes & fees
9.4/10 Exceptional! (71 reviews)
"Lovely, “barefoot chic” hotel that is top class in all respects"
Reviewed on Apr 27, 2026
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 CA $7,079, 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
High-Speed Ferry to St. Barths
CA $114
per adult
78% of travellers recommend
St Maarten Beach hopping tour (Orient beach and Maho beach combo)
CA $84
per adult
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line
CA $222
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
