Windward Holiday Packages

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Top Windward hotels

Rosewood Le Guanahani St Barth

Rosewood Le Guanahani St Barth

Grand Cul De Sac, St. Barthelemy
The price is AU$2,322 per night from 4 May to 5 May
AU$2,322
includes taxes & fees
4 May - 5 May
Rosewood Le Guanahani St Barth: Pet-friendly hotel with free breakfast and free WiFi. Located on the beach.
Amazing!
"Everything about the Le Guannahani is amazing! The location in St Barth cannot be more beautiful. The staff is warm, friendly, efficient and frankly there is nothing they could not help me with. The spa, personal training, lesson lessons were all top notch. The food was delicious and the detail to ..."

Reviewed on 11 Mar. 2025

Rosewood Le Guanahani St Barth
Tropical Hotel St Barth

Tropical Hotel St Barth

Baie de St. Jean, St. Barthelemy
The price is AU$2,015 per night from 8 Apr to 9 Apr
AU$2,015
includes taxes & fees
8 Apr - 9 Apr
Tropical Hotel St Barth: Pet-friendly hotel with free WiFi and free valet parking. Located near the bay.
"Unbelievable stay. Gorgeous property with friendly staff. Breakfast everyday was amazing. Walking distance to many shops, restaurants, beach clubs. Concierge helpful with booking reservations, taxis, etc. not one thing to complain about… booking a trip to come back nexy year!"

Reviewed on 18 Feb. 2025

Tropical Hotel St Barth
Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou, 9, St. Barthelemy
The price is AU$1,725 per night from 5 May to 6 May
AU$1,725
includes taxes & fees
5 May - 6 May
Christopher Hotel: Luxury hotel with free breakfast and free WiFi. Located near the airport.
"Staff needs training. It does not take 2-3 staff people to wait on one guest. This makes it difficult for other guests to get help. Certainly the staff was friendly, but organizing how this works would be an improvement. In our “Junior Suite” the toilet switch kept getting stuck and the “refresh” ..."

Reviewed on 16 Mar. 2025

Christopher 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.