Wailea-Makena Ski Vacations 2025/2026

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What are some things I should consider when booking a Wailea-Makena ski trip package?

Yes, you want pristine powder and perfect runs, but take a moment to consider how close you want to be to the slopes, what extras you want from your resort, and—of course—how much après ski you intend to indulge in.

How can I find cheap Wailea-Makena ski packages?

Fly down the slopes during low or shoulder season, either side of , for a ski package to please your purse. Right now, ski trips start at just $622. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in Wailea-Makena?

Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in Wailea-Makena. Book lessons so you can gear up to take on the rest of the mountain with confidence. Après awaits for all after an eventful day in the snow.

How much does a ski trip to Wailea-Makena cost?

Sensational ski trips to Wailea-Makena start from $622. Use the budget filter to find powder at your perfect price. As always, prices and availability are subject to change. Additional terms may apply.

When’s the best time of year to plan a ski trip to Wailea-Makena?

The best time to hit the slopes in Wailea-Makena depends on what you’re looking for. If you’re all about powder-packed pistes and brilliant blue-sky skiing conditions, aim for the middle of the season. Alternatively, if you’re willing to take a chance on start or end of season snow, you’ll bag much cheaper prices —just make sure there’s a spa or après bar to shelter in on white-out days.

Can I book Wailea-Makena ski packages with airfare?

Save money on your snow time by booking your accommodation, airfare, and car rental in a brilliant bundle. It’s both convenient and cash-flow friendly.

Can I book a Wailea-Makena ski trip with free cancellation and/or flexible dates?

Flexibility is always a bonus when you’re flying down the slopes—and it makes for an easier booking process, too. Check the payment option filter to find trips with free cancellation as well as buy now, pay later options.

Why should I book a ski package in Wailea-Makena with Expedia?

Simple search and fantastic filters make it easy to find, build, and book your dream Wailea-Makena ski vacation in just a few clicks. It’s ‘snow’ joke, it really is that easy.