Windward Holidays from AU$32,087

Book a Hotel + Flight or Car together to unlock savings

Photo by Charles Guerrero

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$703 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

The Latest Windward Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Price was AU$34,595, price is now AU$32,087 per person
AU$32,087
per person
10 Mar - 15 Mar
found 1 hour ago
Return flight included
Sydney (SYD) to Gustavia (SBH)
9.8/10 Exceptional! (94 reviews)
A hidden Gem. Relaxing and chill . Great food .

Reviewed on 9 Jan 2026

Le Toiny Hôtel & Beach Club

Le Toiny Hôtel & Beach Club

5 out of 5
Price was AU$43,139, price is now AU$38,549 per person
AU$38,549
per person
10 Mar - 15 Mar
found 1 hour ago
Return flight included
Sydney (SYD) to Gustavia (SBH)
9.8/10 Exceptional! (44 reviews)
It was perfect . It’s a beautiful property and the service was a dream. They thought about and catered to everything proactively.

Reviewed on 4 Aug 2025

Hotel Manapany

Hotel Manapany

5 out of 5
Anse des Cayes
Price was AU$37,612, price is now AU$34,904 per person
AU$34,904
per person
10 Mar - 15 Mar
found 1 hour ago
Return flight included
Sydney (SYD) to Gustavia (SBH)
9.4/10 Exceptional! (66 reviews)
The property was exquisite. The entire staff was incredible, especially Noémie from Reception. She went above and beyond to make our 11th anniversary very memorable. I am already looking forward to a more extended visit to Hotel Manapany.

Reviewed on 15 June 2025

Christopher Hotel

Christopher Hotel

5 out of 5
Price was AU$36,490, price is now AU$33,916 per person
AU$33,916
per person
10 Mar - 15 Mar
found 1 hour ago
Return flight included
Sydney (SYD) to Gustavia (SBH)
9.6/10 Exceptional! (226 reviews)
Best service on the island, incredibly beautiful property. Delicious food.

Reviewed on 31 Dec 2025

GYP SEA Saint Barth

GYP SEA Saint Barth

5 out of 5
Price was AU$35,574, price is now AU$33,864 per person
AU$33,864
per person
10 Mar - 15 Mar
found 1 hour ago
Return flight included
Sydney (SYD) to Gustavia (SBH)
9.8/10 Exceptional! (83 reviews)
Great service Amazing beach club

Reviewed on 24 Nov 2025

Windward Essential Information

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

Our pick of the best Windward Hotel Deals

Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Les Hauts de Saint Jean St. Barthelemy
9.6/10 Exceptional! (97 reviews)
Great service and communication

Reviewed on 10 Dec 2025

Get rates
Tropical Hotel St Barth
Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou, 9 St. Barthelemy
The price is AU$2,892 per night from 1 Feb to 2 Feb
AU$2,892
1 Feb - 2 Feb
includes taxes & fees
9.4/10 Exceptional! (229 reviews)
Best service on the island, incredibly beautiful property. Delicious food.

Reviewed on 31 Dec 2025

Christopher Hotel
Le Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa

5 out of 5
Baie de Grand Cul de Sac St. Barthelemy
The price is AU$4,414 per night from 3 Feb to 4 Feb
AU$4,414
3 Feb - 4 Feb
includes taxes & fees
9.8/10 Exceptional! (82 reviews)
Staff-10/10 Food-10/10 Amenities-10/10 Only thing Le Barthelemy - wish they use cooling bedsheets. Or comforters - that are less warm.

Reviewed on 15 Dec 2025

Le Barthélemy Hotel & Spa
See all 2,350 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
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Frequently asked questions

How much does a Windward holiday package cost?
Explore the best of Windward from as low as AU$32,087. We offer a wonderful selection of rental cars, hotels and flights to suit every style and budget. Pick up even more discounts when you add a couple of tours or activities to your package.
How do I get a cheap travel package to Windward?
One of the simplest ways to save money (and time) is to combine your bookings with Expedia. Hotels, flights, rental cars and activities — we've got them all. Pick and choose a combination that suits you and see your savings stack up. Of course, a package deal is never a one-size-fits-all. That's why Expedia offers over 550 partner airlines and 1 000 000 hotel options around the globe, which lets you customize your Windward adventure.
How far in advance should I book my Windward holiday?
To score discount prices, book early. Airlines generally release flights, along with some of the lowest fares, around 12 months in advance. Hotels, activities and car rental should also be booked well in advance to avoid disappointment. If you're in need of a last-minute getaway to Windward, there are always lots of great deals on Expedia. Book your escape today!
What does an Expedia Windward travel package include?
Hotels, flights and a reliable car for all your road trip adventures. Simply pick and choose your favourite bundle and gain access to great discounts. Once you've made your booking, add on some activities and tours and watch your savings stack up. When it comes to planning your Windward holiday, the choice is all yours!
What should I know before booking a Windward travel package?
So many places to visit, so many things to do. With a travel package, you can check more of them off your list. Combine your flights, hotels and rental cars and score big savings.
Can I choose my airline with a Windward Expedia holiday package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines throughout the world. Our packages give you the freedom to pick from available flights, hotels and activities that fit your needs.
If I'm not able to travel, can I cancel my Windward holiday package?
You can. We understand that things don't always go to plan, so we're here to help if you have to make changes to your Windward holiday package. You may be able to cancel or change your itinerary at no cost if you've booked in the last 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Visit our Customer Service Portal for more information. Also, check your itinerary for the finer details on change fees.

What to do in Windward

High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

AU$112
per adult
80% of travellers recommend
High-Speed Ferry to St. Barths
Panoramic view of vibrant St. Martin

Edge Ferry Tickets to St. Barts

AU$149
per adult
84% of travellers recommend
Edge Ferry Tickets to St. Barts
Love Boat

Full-Day St Barth Private Charter Tour

AU$2,989
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.