Leeward Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ฿27,000 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 ฿24,624 per night from 23 Jul to 24 Jul
฿24,624
฿25,855 total
23 Jul - 24 Jul
includes taxes & fees
9.8/10 Exceptional! (100 reviews)
"Very quiet, nice property that allows relaxing and enjoyment of views of the island. Staff very helpful.. we got lost one night and the front desk staff stayed on the phone to guide us back. Any issue was attended to immediately."

Reviewed on 29 Jun 2026

GYP SEA Saint Barth
Fouquet's Saint-Barth

Fouquet's Saint-Barth

5 out of 5
Rue des Normands, Lieu Dit Lurin St. Barthelemy Leeward
The price is ฿43,633 per night from 3 Aug to 4 Aug
฿43,633
฿45,814 total
3 Aug - 4 Aug
includes taxes & fees
9.8/10 Exceptional! (35 reviews)
"Great location, luxury and very comfortable room with great terrace and best view in St Barts. Will be back!"

Reviewed on 25 May 2026

Fouquet's Saint-Barth
Pearl Beach Hotel

Pearl Beach Hotel

Plage De St. Jean BP1058 St. Barthelemy French West Indies
The price is ฿20,488 per night from 11 Jul to 12 Jul
฿20,488
฿21,513 total
11 Jul - 12 Jul
includes taxes & fees
9.4/10 Exceptional! (201 reviews)
"Pearl Beach Hotel is one of a kind. We went for my girlfriends birthday and loved every minute of our stay. The staff was amazing throughout our time there - they were attentive, patient and helpful. The manager and front desk staff were awesome and always pleasant. The room was immaculate and spacious. ..."

Reviewed on 8 Jun 2026

Pearl Beach Hotel
See all 1,443 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

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Divi Little Bay Beach Day Package

฿1,314
per adult
76% of travellers recommend
Divi Little Bay Beach Day Package
Underwater Sculpture Park Snorkel Adventure

Underwater Sculpture Park Snorkel Adventure

฿1,478
per adult
Underwater Sculpture Park Snorkel Adventure
Pirate Scavenger Hunt in Philipsburg

Pirate Scavenger Hunt in Philipsburg

฿953
per adult
Pirate Scavenger Hunt in Philipsburg
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.