Windward Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Charles Guerrero

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$616 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

Our pick of the best Windward Hotel Deals

Christopher Hotel

Christopher Hotel

5 out of 5
Pointe Milou, 9 St. Barthelemy
The price is NZ$2,014 per night from 20 Apr to 21 Apr
NZ$2,014
20 Apr - 21 Apr
includes taxes & fees
9.6/10 Exceptional! (233 reviews)
Excellent service with a great location. Gladly return to this hotel.

Reviewed on 14 Mar 2026

Christopher Hotel
Tropical Hotel St Barth

Tropical Hotel St Barth

5 out of 5
Les Hauts de Saint Jean St. Barthelemy
The price is NZ$5,112 per night from 28 Mar to 29 Mar
NZ$5,112
28 Mar - 29 Mar
includes taxes & fees
9.8/10 Exceptional! (103 reviews)
The service was excellent - especially the concierge. The staff was friendly and always accommodating. The hotel was beautiful; room was spotless and comfortable. We enjoyed the breakfast thoroughly! Would recommend to everyone!

Reviewed on 12 Feb 2026

Tropical Hotel St Barth
Rosewood Le Guanahani St Barth

Rosewood Le Guanahani St Barth

Grand Cul De Sac St. Barthelemy
The price is NZ$3,625 per night from 18 Apr to 19 Apr
NZ$3,625
18 Apr - 19 Apr
includes taxes & fees
Rosewood Le Guanahani St Barth
See all 2,363 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.

Frequently asked questions

How much does a Windward holiday package cost?
Explore the best of Windward from as low as . 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

NZ$125
per adult
80% of travellers recommend
High-Speed Ferry to St. Barths
Panoramic view of vibrant St. Martin

Edge Ferry Tickets to St. Barts

NZ$167
per adult
84% of travellers recommend
Edge Ferry Tickets to St. Barts
Saint Barth Prestige Private Charter

Saint Barth Prestige Private Charter

NZ$2,667
per traveller
Saint Barth Prestige Private Charter
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.