Windward Vacations & Trips

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.

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.

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!

Hotels, flights and a reliable car for all your road trip adventures. Simply pick and choose your favorite 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 vacation, the choice is all yours!

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.

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.

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 vacation 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.