Leeward Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to €185 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    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 €660 per night from 13 Aug to 14 Aug
€660
13 Aug - 14 Aug
includes taxes & fees
9.6/10 Exceptional! (79 reviews)
"This property provided an exceptional guest experience. The meticulous attention to detail within the accommodations, designed to enhance the overall vacation experience, was truly remarkable. Furthermore, the logistical planning and transportation arrangements were flawlessly executed. We anticipate ..."

Reviewed on 24 Jul 2025

GYP SEA Saint Barth
Pearl Beach Hotel

Pearl Beach Hotel

Plage De St. Jean BP1058, St. Barthelemy, French West Indies
The price is €510 per night from 2 Aug to 3 Aug
€510
2 Aug - 3 Aug
includes taxes & fees
9.2/10 Wonderful! (176 reviews)
"Pearl beach was a beautiful surprise for us. From the convenient pick up and drop off at airport. Even though we changed our flight twice to early check in and Late check out. Kind and catering staff. Perfect size rooms. Perfect location. It has it all. Thank you team pearl"

Reviewed on 22 Jul 2025

Pearl Beach Hotel
Reve de Saint Barth

Reve de Saint Barth

Les Hauts de Flamands, Merlette, St. Barthelemy
9.8/10 Exceptional! (42 reviews)
"Everything was fantastic. The manger was amazing and helped us with everything that we needed. Would love to stay here again. Thank you"

Reviewed on 29 Jul 2025

Get rates
Reve de Saint Barth
See all 1,459 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

St Maarten Shore Excursion: Maho Beach Round-Trip Transfer

St Maarten Shore Excursion: Maho Beach Round-Trip Transfer

€23
per adult
St Maarten Shore Excursion: Maho Beach Round-Trip Transfer
Sunset view at Maho Beach

Amazing Plane Spotting at Maho Beach

€23
per adult
Amazing Plane Spotting at Maho Beach
Lunch at Meads BAy

Ultimate Prickly Pear and Anguilla Experience

€128
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.