Wintergreen Vacation Packages 2026 from $572

Wintergreen flight + hotel vacation packages

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

Shenandoah Wilderness Traveler

$572

per person

Jun 5 - Jun 11

found 6 hours ago

Roundtrip flight included

Chicago (ORD) to Charlottesville (CHO)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, laundry facilities, and barbecue grills are also on offer.

Virginia Guesthouse Hotel

Lewis Mountain

Save 100% on your flight

$1,150

per person

Jun 5 - Jun 11

found 6 hours ago

Roundtrip flight included

Chicago (ORD) to Charlottesville (CHO)

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A 24-hour business center, a coffee shop, and a snack bar/deli are also on offer.

English Inn of Charlottesville

The Meadows

$788

per person

Jun 5 - Jun 11

found 6 hours ago

Roundtrip flight included

Chicago (ORD) to Charlottesville (CHO)

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Oakhurst Inn at the University

Jefferson Park Avenue

$1,321

per person

Jun 5 - Jun 11

found 6 hours ago

Roundtrip flight included

Chicago (ORD) to Charlottesville (CHO)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Enjoy the sauna and conveniences like a 24-hour front desk and concierge services.

Sonesta ES Suites Charlottesville University

Barracks Road

$766

per person

Jun 5 - Jun 11

found 6 hours ago

Roundtrip flight included

Chicago (ORD) to Charlottesville (CHO)

This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.

Top Wintergreen hotels deals

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Roseland VA

$216 nightly

$242 total

May 6 - May 7

Total with taxes and fees

A hot tub is featured at this condo, along with laundry facilities.

Pool

Hot Tub

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

Best views on Mountain! Breathtaking 5 Star condo! AVAIL April 17-19 weekend!

Wintergreen VA

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A sauna is featured at this condo, along with laundry facilities and barbecue grills.

Kitchen

Washer

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.

Pool

Hot Tub

Endless Mountain Top Views from All The Way Up!

Wintergreen Resort VA

$203 nightly

$228 total

May 4 - May 5

Total with taxes and fees

This condo features laundry facilities.

Pool

Kitchen

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

Roseland VA

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This condo features laundry facilities.

Kitchen

Washer

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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.

Popular places to visit

Wintergreen Resort

4.5/5(80 reviews)

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

Bold Rock Hard Cider Nellysford Cidery

4.5/5(6 reviews)

You can take time to visit Bold Rock Hard Cider Nellysford Cidery during your travels to Wintergreen. Discover the mountain views in this family-friendly area, or seek out the ski slopes.

Stoney Creek Golf Course

Enjoy a round of golf in Wintergreen at Stoney Creek Golf Course. Discover the mountain views and top-notch restaurants in this vibrant area.

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 $572. 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.