Windward Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Charles Guerrero
  • Plan, book, travel with confidence

  • Better together

    Save up to £750 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

    Packages with flights are ATOL protected

Top Windward Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Christopher Hotel

Christopher Hotel

Pointe Milou
£5,843
per person
4 Nov - 12 Nov
found 23 hours ago
Return flight included
London (LHR) to Gustavia (SBH)
9.6/10 Exceptional! (262 reviews)
Hotel Manapany

Hotel Manapany

Anse des Cayes
Save 100% on your flight
£10,284
per person
4 Nov - 12 Nov
found 23 hours ago
Return flight included
London (LHR) to Gustavia (SBH)
9.4/10 Exceptional! (71 reviews)
Lovely, “barefoot chic” hotel that is top class in all respects

Reviewed on 27 Apr 2026

Le Toiny Hôtel & Beach Club

Le Toiny Hôtel & Beach Club

Toiny
Save 100% on your flight
£9,022
per person
4 Nov - 12 Nov
found 23 hours ago
Return flight included
London (LHR) to Gustavia (SBH)
9.8/10 Exceptional! (55 reviews)
Le Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa

Grand Cul-de-Sac
£11,154
per person
4 Nov - 12 Nov
found 23 hours ago
Return flight included
London (LHR) to Gustavia (SBH)
9.8/10 Exceptional! (91 reviews)

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

Pointe Milou, 9 St. Barthelemy
Christopher Hotel
Le Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa

Baie de Grand Cul de Sac St. Barthelemy
Le Barthélemy Hotel & Spa
Tropical Hotel St Barth

Tropical Hotel St Barth

Les Hauts de Saint Jean St. Barthelemy
Tropical Hotel St Barth
See all 2,348 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.

Frequently asked questions

How much does a Windward travel package cost?
Starting from as low as £5,843, 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.

What to do in Windward

High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

£60
per adult
80% of travellers recommend
High-Speed Ferry to St. Barths
Love Boat

Full-Day St Barth Private Charter Tour

£1,455
per traveller
Full-Day St Barth Private Charter Tour
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.