Windward Holiday Packages

Save when you book Windward package deals

Choose two or more items and save on your trip:

Top Windward hotels

Rosewood Le Guanahani St Barth

Rosewood Le Guanahani St Barth

Grand Cul De Sac, St. Barthelemy
The price is AU$2,385 per night from 30 Nov to 1 Dec
AU$2,385
30 Nov - 1 Dec
includes taxes & fees
Rosewood Le Guanahani St Barth: Pet-friendly hotel with free breakfast and free WiFi. Located on the beach.
DID NOT GO TO SPA/ UPSET WE WERE NOT ABLE TO USE POOL ONE AFTERNOON DUE TO A CHILD WAS IN POOL WITHOUT ANY SWIM DIAPERS AND HAD AN ACCIDENT

Reviewed on 4 Nov 2025

Opens in a new windowRosewood Le Guanahani St Barth
Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Les Hauts de Saint Jean, St. Barthelemy
Tropical Hotel St Barth: Luxury hotel with free breakfast and free WiFi. Located near the beach.
Great people very welcoming. I highly recommend this place. Great environment. Beautiful views

Reviewed on 4 Nov 2025

Opens in a new windowTropical Hotel St Barth
Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou, 9, St. Barthelemy
The price is AU$1,903 per night from 11 Nov to 12 Nov
AU$1,903
11 Nov - 12 Nov
includes taxes & fees
Christopher Hotel: Luxury hotel with free breakfast and free WiFi. Located by the ocean.
Clean room, wonderful service, very good Staff

Reviewed on 4 Nov 2025

Opens in a new windowChristopher Hotel
Don't see what you're looking for?
See all available properties in Windward
View all properties
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.

Your guide to epic deals and sweet holiday packages to Windward

How much are holiday packages to Windward?

You can book an awesome holiday in Windward from just on Wotif. Check our deal cards for details.

What’s included in Wotif’s Windward holiday package deals?

Windward packages can bundle everything: flight + hotel + car hire. But you can go for hotel + car hire without the flight. Or flight + hotel. You do you.

Can I cancel my Windward holiday plans on Wotif?

Yes. Within 24 hours of booking, you can cancel and get your money back on many of our packages. After 24 hours, your airline or hotel may charge a fee. Check your itinerary or our Customer Service Portal to know more.

How do I find the best holiday package to Windward?

Just take a look through all our terrific offers or select your dream spot in Windward, and we’ll serve up some delicious Windward holiday deals that’ll make you swoon and save you cash.

How do I get the best holiday deals to Windward?

We have stacks of ready-made holidays and luxury getaways in Windward, and usually the more flexible you can be on dates, the better the deal. Simply enter your travel details and we’ll find you loads of wallet-friendly deals. You can filter by trip length, hotel stars and flight class and – ta-daa – best break ever. Added bonus: our Price Promise refunds the difference if you find a lower price up to 24 hours before check-in.

When is the best time to visit Windward?

usually has the best bargain breaks when hotel prices are often cheaper, and Windward is quieter. But for more of a buzz, plan your visit in .

Why choose Wotif to book your holiday package to Windward?

Plan your trip to Windward today and you could save on your next escape and pay just . With Wotif, you know you’ve got great flexibility and those awesome Mates Rates deals, too.