Leeward Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 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

Top hotels in Leeward

GYP SEA Saint Barth

GYP SEA Saint Barth

5 out of 5
Le Colombier St. Barthelemy
The price is €1,109 per night from 16 Nov to 17 Nov
€1,109
16 Nov - 17 Nov
includes taxes & fees
GYP SEA Saint Barth
Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes St. Barthelemy
The price is €1,036 per night from 16 Nov to 17 Nov
€1,036
16 Nov - 17 Nov
includes taxes & fees
9.4/10 Exceptional! (71 reviews)
"Lovely, “barefoot chic” hotel that is top class in all respects"

Reviewed on 27 Apr 2026

Hotel Manapany
Reve de Saint Barth

Reve de Saint Barth

Les Hauts de Flamands, Merlette St. Barthelemy
The price is €1,021 per night from 15 Nov to 16 Nov
€1,021
15 Nov - 16 Nov
includes taxes & fees
9.8/10 Exceptional! (71 reviews)
"I would like to thank Ninon for an great experience while visiting the property at Rêve de St. Barth. We appreciated the innovative architectural design and felt like we were special how the staff treated us. Lovely setting in the hills of St.Barth with a view of the ocean from the second floor bedroom. ..."

Reviewed on 30 Sept 2026

Reve de Saint Barth
See all 1,441 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 holiday package cost?
The most affordable Leeward holiday 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 travelling style.
How do I get a cheap travel package to Leeward?
Crafting your own Leeward holiday 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 holiday?
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 holiday!
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 favourite 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 holiday plans, there's bound to be a package that best suits your budget.
Can I choose my airline with a Leeward Expedia holiday package?
Yes, you're in control. We offer more than 550 partner airlines globally, so you can customize your Leeward holiday according to your needs and budget.
If I'm not able to travel, can I cancel my Leeward holiday package?
Don't worry if you're rethinking your Leeward holiday 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

Meads BAy Floating Bar

Ultimate Anguilla Cays & Coves

€134
per adult
Ultimate Anguilla Cays & Coves
Seaview Beach Hotel Pool Pass/Cabana Rental

Seaview Beach Hotel Pool Pass/Cabana Rental

€18
per adult
Seaview Beach Hotel Pool Pass/Cabana Rental
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

€143
per adult
92% 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.