Leeward Holidays

Photo by Charles Guerrero

  • Plan, book, travel with confidence

  • Better together

    Save up to €185 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 €842 per night from 16 Dec to 17 Dec
€842
16 Dec - 17 Dec
includes taxes & fees
9.6/10 Exceptional! (84 reviews)
Great service Amazing beach club

Reviewed on 24 Nov 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 €1,838 per night from 16 Dec to 17 Dec
€1,838
16 Dec - 17 Dec
includes taxes & fees
9.6/10 Exceptional! (26 reviews)
A superb hotel in Gustavia with easy access to beach and dining

Reviewed on 2 Aug 2025

Hotel Barrière Le Carl Gustaf St Barth
Pearl Beach Hotel

Pearl Beach Hotel

Plage De St. Jean BP1058 St. Barthelemy French West Indies
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 7 Oct 2025

Get rates
Pearl Beach Hotel
See all 1,516 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.

Popular places to visit

Colombier Beach

Colombier Beach

If a restful holiday is part of your travel plans, Colombier Beach might be the perfect place to visit during your trip to Colombier.

Colombier Beach

What to do in Leeward

Sightseeing Tour of the French and Dutch Sides of the Island

St-Martin and St Maarten: Sightseeing Tour of the French and Dutch Sides of the Island

€43
per adult
92% of travellers recommend
St-Martin and St Maarten: Sightseeing Tour of the French and Dutch Sides of the Island
St. Maarten Maho Beach Tour

St. Maarten Maho Beach Tour

€34
per adult
80% of travellers recommend
St. Maarten Maho Beach Tour
St Maarten Beach hopping tour

St Maarten Beach hopping tour (Oreint beach and Maho beach combo)

€52
per adult
St Maarten Beach hopping tour (Oreint beach and Maho beach combo)
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.