Windward Holiday Packages

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Top Windward hotels

Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Les Hauts de Saint Jean St. Barthelemy
The price is AU$1,360 per night from 14 Apr to 15 Apr
AU$1,360
14 Apr - 15 Apr
includes taxes & fees
Tropical Hotel St Barth: Luxury hotel with free breakfast and free WiFi. Located near the bay.
Beautiful hotel, clean and spacious rooms, AMAZING STAFF ⭐️⭐️⭐️⭐️⭐️

Reviewed on 23 Mar 2026

Opens in a new windowTropical Hotel St Barth
Rosewood Le Guanahani St Barth

Rosewood Le Guanahani St Barth

Grand Cul De Sac St. Barthelemy
The price is AU$3,173 per night from 9 Apr to 10 Apr
AU$3,173
9 Apr - 10 Apr
includes taxes & fees
Rosewood Le Guanahani St Barth: Luxury hotel with free breakfast and free WiFi. Located on the beach.
Fabulous hotel. The staff were incredible

Reviewed on 20 Mar 2026

Opens in a new windowRosewood Le Guanahani St Barth
Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou, 9 St. Barthelemy
The price is AU$1,486 per night from 3 May to 4 May
AU$1,486
3 May - 4 May
includes taxes & fees
Christopher Hotel: Luxury hotel with free breakfast and free WiFi. Located near the airport.
Excellent service with a great location. Gladly return to this hotel.

Reviewed on 14 Mar 2026

Opens in a new windowChristopher Hotel
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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.