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Have you been telling yourself, “2024 is the year I travel more and sit less”? Well, here we are and there you are. So, where are you going? Looks like a flight to Windward is calling. Good thing we can help you bag that flight out of town for cheap, so you can get your resolutions resolved.

Travel like you mean it

When you land it’s not straight to the tourist traps for you. You have things to do and see in Windward that aren’t on a map or in the “Best of. . .” guides. You know this region is filled with hidden haunts, locals-only know favorites, and the off-beat-so-weird-it’s-amazing places. And you plan to find every last one of them. Good thing you’ll save a grip of cash on your flight so you can daytrip far and wide.

You won’t have to wing it

So how do you score that killer deal on a flight to Windward? Easy, go through us. These aren’t pie in the sky deals, but ones you can actually score. Filter flights to Windward by:

  • Hotwire Hot Rate: Do you have a flexible schedule? Hit up the Hotwire Hot Rate and land a super cheap flight to Windward. We’ll reveal the airline and exact time after you book.
  • Price: How low can we go? Find out. We have prices from to .
  • Duration: Want to get to Windward as fast as you can? Or maybe you don’t mind taking your time to save a few bucks here and there.
  • Departure or Arrival: Like to arrive in the a.m. to get your day going? Or are you a night owl that knows the best fun happens late night? The choice is yours.

So are you going to live up to those travel plans or kick the can to next year? Book your flight to Windward today and get going.

Last Minute Hotel Deals in Windward

Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou, 9, St. Barthelemy
The price is $1,009 per night from Oct 25 to Oct 26
$1,009
includes taxes & fees
Oct 25 - Oct 26
Stay at this 5-star luxury hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (196 reviews)
"Amazing hotel. Have stayed twice and still think one if the best options in St Barts!"

Reviewed on Jul 15, 2024

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 $2,107 per night from Oct 24 to Oct 25
$2,107
includes taxes & fees
Oct 24 - Oct 25
Stay at this 5-star luxury hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free valet parking. Popular attractions Gustavia Harbor and Grand Cul ...
9.6/10 Exceptional! (67 reviews)
"Spectacular place, with extra class service and attention to all the details. Special thanks to Eva who treated us like family in the restaurant and Maria for our welcome."

Reviewed on Jul 16, 2024

Le Barthélemy Hotel & Spa
Rosewood Le Guanahani St Barth

Rosewood Le Guanahani St Barth

Grand Cul De Sac, St. Barthelemy
The price is $1,085 per night from Oct 29 to Oct 30
$1,085
includes taxes & fees
Oct 29 - Oct 30
Book a stay at this beach hotel in St. Barthelemy. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Gustavia Harbor and Grand Cul de Sac ...
9.6/10 Exceptional! (33 reviews)
"We had a great experience at the Rosewood. We have been several rosewood properties and they are all great. In particular, the “manager” and Rudolph who picked us up, treated us like special guests. Highly recommend."

Reviewed on Aug 3, 2024

Rosewood Le Guanahani St Barth
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Tropical Hotel St Barth

Tropical Hotel St Barth

Baie de St. Jean, St. Barthelemy
The price is $849 per night from Oct 20 to Oct 21
$849
includes taxes & fees
Oct 20 - Oct 21
Book a stay at this beach hotel in St. Barthelemy. Enjoy free WiFi, free valet parking, and a 24-hour front desk. Our guests praise the helpful staff and the ...
9.6/10 Exceptional! (60 reviews)
Great stay.
"The service is perfect, the staff is super friendly and go the extra mile for there guest. Will stay again."

Reviewed on Aug 1, 2024

Tropical Hotel St Barth
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.