Wintergreen Vacation Packages 2026 from $1,278

Wintergreen flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Basecamp151

$1,278

per person

Nov 25 - Nov 29

found 13 hours ago

Roundtrip non-stop flight included

Tampa (TPA) to Charlottesville (CHO)

This motel features a coffee shop, a virtual front desk, and free self parking. WiFi in public areas is free. A communal living room is also provided.

Stoney Creek Cottage Wintergreen w EV Charger

$2,368

per person

Nov 25 - Nov 29

found 13 hours ago

Roundtrip non-stop flight included

Tampa (TPA) to Charlottesville (CHO)

This apartment doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden is also provided.

Top Wintergreen hotels deals

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Roseland VA

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This condo features laundry facilities.

Highlands Condo Views for days! Tons of details listed ⬇️☺️

Wintergreen Resort VA

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Ski-in/ski-out access and an outdoor pool are featured at this smoke-free condo. Laundry facilities are provided for your convenience.

Pool

Kitchen

New Build! Log Cabin with Hot Tub in Wintergreen

Wintergreen Resort VA

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A hot tub is featured at this cabin, along with laundry facilities and barbecue grills.

Endless Mountain Top Views from All The Way Up!

Wintergreen Resort VA

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This condo features laundry facilities.

Pool

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Large and Luxurious Exec 5BR Chalet

Wintergreen Resort VA

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This vacation home features ski-in/ski-out access, laundry facilities, and barbecue grills.

Kitchen

Washer

Cozy Cabin with private HOT TUB!

Nellysford VA

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A hot tub is featured at this cabin, along with laundry facilities and barbecue grills.

Hot Tub

Kitchen

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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.

Stay near popular Wintergreen attractions

A waterfall in a forest with autumn leaves.

Wintergreen Resort

8.8/10 (140 reviews)

Hit the slopes in Wintergreen with a visit to Wintergreen Resort. Discover the mountain views and top-notch restaurants in this vibrant area.

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Frequently asked questions

How much are vacation packages to Wintergreen?

With a Travelocity vacation package, you could be living it up in Wintergreen for a mere $1,278. Flights, tours and hotels — we've got you. You'll save a bunch just by bundling together your bookings. With everything taken care of before you leave, you can sit back, relax and enjoy the adventure.

How long should my Wintergreen vacation be?

Many travelers pack their bags and vacation in Wintergreen for around 3 nights. That gives you a rough guide, but don't let it restrict you. Whether you stay for a day or two to see the big attractions or hang around to experience this place like a local, an unforgettable adventure awaits.

Where can I get the best vacation package deals for Wintergreen?

Travelocity can help you snag a terrific Wintergreen package deal. With no less than 400 airlines and 1,000,000 properties across the world, you're sure to find the perfect mix.

Why should I book my Wintergreen vacation bundle with Travelocity?

Because you'll never roam alone if you book through us, and we offer 24/7 customer support and first-rate service to boot. Add to that our Price Match Guarantee and countless experiences and destinations to select from. We're here to help you have the trip of a lifetime.

Can I save on my Wintergreen car rental if I bundle it with a hotel or flight?

Combining your hotel, flight and car into a Wintergreen vacation package is the easiest way to land the best deal. Plus, having your own rental car gives you absolute freedom to get to all those big-name sights you want to check out. Situated 120 mi from Wintergreen, White House is one place that should feature on your itinerary. Load up the car and make a day trip of it.

Which airport is best for Wintergreen?

Charlottesville-Albemarle Airport (CHO) (30 mi away from the city center), Lynchburg Regional Airport (LYH) (40 mi away from central Wintergreen) and Shenandoah Valley Regional Airport (SHD) (25 mi away from central Wintergreen) are the best options for Wintergreen.

Where should I stay when visiting Wintergreen?

If you're searching for somewhere to lay your head, consider the Mountain Inn Lodge 70 with Wintergreen Advantage. It's the top pick for many visitors.