Leeward Holidays

Photo by Charles Guerrero

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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 9 Feb to 10 Feb
€1,109
9 Feb - 10 Feb
includes taxes & fees
9.6/10 Exceptional! (88 reviews)
Beautiful property, good food. Loved the decor. Having dedicated beach chairs at Gyp sea Beach club was a huge plus. The best beach in my opinion! Staff was so friendly and responsive. Would definitely stay here again.

Reviewed on 24 Jan 2026

GYP SEA Saint Barth
Reve de Saint Barth

Reve de Saint Barth

Les Hauts de Flamands, Merlette St. Barthelemy
9.8/10 Exceptional! (52 reviews)
If you’re looking for tranquility, elegance, and an authentic St. Barts escape, Le Rêve de Saint Barth is absolutely exceptional. A place you’ll want to return to again and again ✨

Reviewed on 23 Jan 2026

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Reve de Saint Barth
Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes St. Barthelemy
The price is €2,117 per night from 1 Feb to 2 Feb
€2,117
1 Feb - 2 Feb
includes taxes & fees
9.2/10 Wonderful! (66 reviews)
The property was exquisite. The entire staff was incredible, especially Noémie from Reception. She went above and beyond to make our 11th anniversary very memorable. I am already looking forward to a more extended visit to Hotel Manapany.

Reviewed on 15 Jun 2025

Hotel Manapany
See all 1,461 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 which includes landscape views, a bay or harbor and general coastal views

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 Maho Beach Tour

St. Maarten Maho Beach Tour

€33
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)

€50
per adult
St Maarten Beach hopping tour (Oreint beach and Maho beach combo)
Amazing Plane Spotting at Maho Beach

Amazing Plane Spotting at Maho Beach

€22
per adult
Amazing Plane Spotting at Maho Beach
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.