Windward Islands Mountain Vacations and Getaways

The first step to planning your mountain vacation to Windward Islands is to decide what dates you want to go. In the winter months, fresh snowfall means you could hit the slopes at ski resorts near Windward Islands, while summer invites you to enjoy scenic hikes. It's a good idea to choose the type of accommodation you'd prefer, too. On Expedia, you'll encounter a vast array of options in Windward Islands, from famous chain hotels to charming cabins. The vacation planning page has more tips for organizing your Windward Islands mountain vacation.

When booking accommodation for your mountain vacation to Windward Islands, check to see if where you're staying has heating. Windward Islands's mountain air means it can feel fresh at night. If you're craving a special stay, look to see if the hotel offers mountain view rooms, or has a pool or hot tub to unwind in the evenings. Expedia's handy search filters include all these amenities and more, making it a breeze to book the right place to stay on your Windward Islands vacation package.

Choosing a package for your Windward Islands vacation often works out cheaper thanks to the savings you get for bundling up your flights and hotel. You'll typically find it costs more when booking these separately. On Expedia, the green label even shows you how much you're saving. Packages also tend to be more flexible, meaning it's more likely you can cancel for free in case your 2026 plans change. You can usually secure your package by paying a small upfront deposit, whereas booking flights separately requires full payment.

Return flight tickets, your accommodation, and applicable taxes are typically included when you book a mountain vacation package to Windward Islands from $1,303. Hotels may include breakfast and Wi-Fi, while the airfare may include checked luggage. Certain resorts may even include ski passes. As each Windward Islands vacation package is different, be sure to double-check what's included before you confirm. If you want a hassle-free trip, consider booking Windward Islands all-inclusive vacation packages as these include all meals.

Comparing some of the best deals using the search wizard is one of the first steps to booking your Windward Islands mountain vacation on Expedia. Take advantage of the search filters to narrow down hundreds of options at the click of a button. If you've got a strict budget, use the maximum price filter to set your limit. When you've pinned down your Windward Islands package vacation, book it in just a few clicks. You'll also have the option to spread the cost with Expedia's payment plans.

With meaty exclusive deals you won't find anywhere else, you'll keep more cash in your pocket when booking your Windward Islands vacation package on Expedia. No matter your preferences or tastes, you'll find the right place to stay thanks to the wide selection of accommodation. There are even last-minute deals, too. And if that's not enough, join One Key for free. Expedia's reward program lets you earn points on eligible trips and also gives you access to juicy member-only discounts.

Yes, as most of Expedia's mountain vacation packages to Windward Islands are flexible, you can often cancel for free. Doing so is easy, too—log in to the “Trips” section and follow the steps. Don't forget to double-check the cancellation policy before booking, as not all Windward Islands vacation packages are flexible. The good news is Expedia will display this to you before payment. Take advantage of the free cancellation search filter so you'll be able to narrow down your search to view only flexible Windward Islands vacation packages.

5-star hotels, cozy mountain lodges, and quaint bed and breakfasts are some of the most popular types of mountain accommodations for your vacation to Windward Islands. Don't forget to use the filters to home in the amenities you'd like to have, too. Maybe it's a spacious suite with a mountain view or a traditional lobby with a fireplace—you'll find it all with Expedia's easy-to-use search wizard and wide choice of accommodation.