Wintergreen Vacation Packages 2026 from $451

Wintergreen flight + hotel vacation packages

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

Lafayette Inn

$451

per person

Feb 13 - Feb 16

found 6 hours ago

Roundtrip flight included

Charlotte (CLT) to Charlottesville (CHO)

A restaurant and a bar/lounge are featured at this bed & breakfast. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A terrace, concierge services, and wedding services are also on offer.

Foxfield Inn

$603

per person

Feb 13 - Feb 16

found 6 hours ago

Roundtrip flight included

Charlotte (CLT) to Charlottesville (CHO)

This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free full breakfast each morning. A terrace, a garden, and a library are also on offer.

Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

$715

per person

Feb 13 - Feb 16

found 6 hours ago

Roundtrip flight included

Charlotte (CLT) to Charlottesville (CHO)

This cabin includes express check-out and a virtual front desk. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Take advantage of the free self parking.

Top Wintergreen hotels deals

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

Roseland VA

$216 nightly

$242 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

A water park and a hot tub are featured at this smoke-free condo. Laundry facilities are provided for your convenience.

Pool

Hot Tub

The Modern Mountain Condo

Wintergreen Resort VA

$252 nightly

$283 total

Jan 13 - Jan 14, 2026

Total with taxes and fees

This condo features laundry facilities.

Pool

Kitchen

Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC

Wintergreen Resort VA

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This condo features laundry facilities.

Kitchen

Washer

Lofty Pursuits: Spectacular View + EV Charger

Wintergreen Resort VA

$387 nightly

$413 total

Jan 14 - Jan 15, 2026

Total with taxes and fees

Book a stay at this ski cabin in Wintergreen. Enjoy free WiFi, ski-in/ski-out access, and an in-room coffeemaker. Popular attractions Wintergreen Resort and Raven's Roost Overlook are located nearby.

Kitchen

Washer

Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!

Wintergreen VA

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This condo features an outdoor pool and an indoor pool. There's a hot tub on site, and laundry facilities and barbecue grills are also offered.

Pool

Hot Tub

Wow! What A View!

Wintergreen Resort VA

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An outdoor pool is featured at this condo, along with laundry facilities.

Pool

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.

Popular places to visit

Wintergreen Resort

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

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 $451. 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.