Leeward Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

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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$1,293 per night from 15 Aug to 16 Aug
NZ$1,293
15 Aug - 16 Aug
includes taxes & fees
9.6/10 Exceptional! (81 reviews)
"We loved this hotel, however there were no locks on the door of one of the bedrooms in our suite. The room could be accessed from the outside. The hotel is on a beautiful hilltop but, we couldn’t let our kids sleep in that room. The hotel had no way to rectify. The hotel and staff are amazing but ..."

Reviewed on 1 Aug. 2025

GYP SEA Saint Barth
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

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Reve de Saint Barth
Pearl Beach Hotel

Pearl Beach Hotel

Plage De St. Jean BP1058, St. Barthelemy, French West Indies
The price is NZ$1,000 per night from 21 Aug to 22 Aug
NZ$1,000
21 Aug - 22 Aug
includes taxes & fees
9.2/10 Wonderful! (178 reviews)
"Excellent services."

Reviewed on 4 Aug. 2025

Pearl Beach Hotel
See all 1,468 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$125
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$166
per adult
84% of travellers recommend
Edge Ferry Tickets to St. Barts
Sky Explorer and Flying Dutchman

Sky Explorer and Flying Dutchman

NZ$154
per adult
74% of travellers recommend
Sky Explorer and Flying Dutchman
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.