Windward 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 £335 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

    Packages with flights are ATOL protected

Windward Essential Information

Language
French
Currency
Euros
Local Welcome
Salut / Bonjour
Local Goodbye
Au revoir / À bientôt
Closest Airport
Gustaf III Airport (SBH)

Top hotels in Windward

Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou, 9, St. Barthelemy
9.4/10 Exceptional! (224 reviews)
"The breakfast is amazing! However did not enjoy the dinner,"

Reviewed on 10 Aug 2025

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Christopher Hotel
Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Les Hauts de Saint Jean, St. Barthelemy
9.6/10 Exceptional! (91 reviews)
"Expensive but it's St Barts as expected...this an amazing hotel.,loved the location, the views, the service,the rooms and Beeakfast was good as well..will definitely go back again.10/10"

Reviewed on 31 Jul 2025

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Tropical Hotel St Barth
Rosewood Le Guanahani St Barth

Rosewood Le Guanahani St Barth

Grand Cul De Sac, St. Barthelemy
9.8/10 Exceptional! (54 reviews)
Excellent Stay
"Superior service."

Reviewed on 14 May 2025

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Rosewood Le Guanahani St Barth
See all 2,328 properties in Windward
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Windward travel package cost?
Starting from as low as , you can create your own Windward travel package. Simply bundle flights, hotels and car rentals and we'll reward you with discounts.
If I'm not able to travel, can I cancel my Windward travel package?
It's impossible to predict what the future holds, so it's comforting to know that you can cancel or change your Windward travel package. If your booking was made in the last 24 hours, you may be entitled to a refund. If it's an older booking, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to learn more.
How do I get a cheap travel package to Windward?
Combine your bookings with Expedia to save big on your next exciting adventure. With more than 550 airlines and 1,000,000 hotels worldwide, your Windward holiday package can be tailored exactly to suit your travel style. With all that extra money, why not add a few exciting tours and experiences? It's an easy way to unlock even more bargains. That holiday you've always dreamed of in Windward is much closer than you thought!
Does Expedia offer Book Now, Pay Later Windward holidays?
Expedia has joined forces with online lender Klarna to make your next trip easier on your wallet. Paying in instalments means you can spread the costs of your next dream escape, leaving you with more money to play with while you're travelling. Klarna has several payment plans to choose from, so you're sure to find something that fits your budget. Check out these flexible payment options:

  • Pay monthly holidays: Klarna has easy monthly payment plans that fit all budgets, so you can escape on that well-earned holiday now.
  • Pay in instalments holidays: Like the idea of paying off your holiday in multiple transactions? Then select this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the total upfront) makes it easier to click that "book now" button, opt for a low deposit holiday payment plan with Klarna.

How far in advance should I book my Windward holiday?
It can be hard to know exactly when the best time is to book your Windward holiday. But generally the earlier you book, the better the prices. Sometimes, you can reserve your flights and hotels up to 12 months before departure. If you're considering a last-minute getaway, no need to worry! There are fabulous bargains advertised on Expedia every single day.
What does an Expedia Windward travel package include?
Expedia has all you need to arrange your Windward trip, but how you structure your package is your call. Select from any combination of rental cars, hotels and flights. Chasing some activities or tours to keep you on the go? Once you've made your booking, you can add them on too. No matter your budget, there's a package deal to meet your needs.
What should I know before booking a Windward travel package?
When you book your hotels, flights and car rentals together, you'll pick up great discounts. Whether you're organising a rural escape in a cottage or would rather stay in a ritzy city hotel, Expedia can make it happen for less.
Can I choose my airline with a Windward Expedia travel package?
Yes, the choice is all yours. Expedia has access to more than 550 partner airlines throughout the world, so you can tailor your Windward holiday according to your style and budget.

Popular places to visit

Gouverneur Beach

Gouverneur Beach

Why not spend a care-free afternoon at Gouverneur Beach during your travels in Anse du Gouverneur?

Gouverneur Beach

What to do in Windward

Plage de Saint-Jean

Full-Day St Barth Private Charter Tour

£1,466
per traveller
Full-Day St Barth Private Charter Tour
High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

£56
per adult
76% of travellers recommend
High-Speed Ferry to St. Barths
See all activities in Windward

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.