Leeward Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to NZ$616 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Our pick of the best Leeward Hotel Deals

GYP SEA Saint Barth
GYP SEA Saint Barth
5 out of 5
Le Colombier, St. Barthelemy
The price is NZ$1,486 per night from 26 July to 27 July
NZ$1,486
26 July - 27 July
includes taxes & fees
9.6/10 Exceptional! (73 reviews)
"Best hotel experience ever"

Reviewed on 20 Jun. 2025

GYP SEA Saint Barth
Pearl Beach Hotel
Pearl Beach Hotel
Plage De St. Jean BP1058, St. Barthelemy, French West Indies
The price is NZ$985 per night from 27 June to 28 June
NZ$985
27 June - 28 June
includes taxes & fees
9.2/10 Wonderful! (170 reviews)
"Small boutique hotel. Great high ceiling spacious rooms. Great staff always respond promptly. Great beach. Great food. Quiet. Just book it."

Reviewed on 29 May 2025

Pearl Beach Hotel
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 NZ$2,620 per night from 27 July to 28 July
NZ$2,620
27 July - 28 July
includes taxes & fees
9.6/10 Exceptional! (25 reviews)
"Wonderful staff, beautiful ac"

Reviewed on 20 May 2025

Hotel Barrière Le Carl Gustaf St Barth
See all 1,464 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

High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

NZ$124
per adult
76% of travellers recommend
High-Speed Ferry to St. Barths
Panoramic view of vibrant St. Martin

Edge Ferry Tickets to St. Barts

NZ$165
per adult
84% of travellers recommend
Edge Ferry Tickets to St. Barts
Lunch at Meads BAy

Ultimate Prickly Pear and Anguilla Experience

NZ$248
per adult
80% 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.