Wintergreen Vacation Packages 2026 from $807

Wintergreen flight + hotel vacation packages

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

Virginia Guesthouse At University Of Virginia

Lewis Mountain

$807

per person

Apr 10 - Apr 12

found 1 day ago

Roundtrip flight included

New York (NYC) 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.

Little Mod Hotel at the University

Venable

$869

per person

Mar 27 - Mar 29

found 1 day ago

Roundtrip flight included

New York (NYC) to Charlottesville (CHO)

This hotel features a restaurant, free WiFi in public areas, and a picnic area. 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. Express check-in and express check-out are also provided.

Wintergreen Retreat Jacuzzi Sauna dog Friendly

Treeloft

$3,526

per person

May 15 - May 17

found 23 hours ago

Roundtrip non-stop flight included

New Orleans (MSY) to Charlottesville (CHO)

This vacation home includes free WiFi in public areas and barbecue grills.

Oakhurst Inn at the University

Jefferson Park Avenue

$859

per person

Mar 27 - Mar 29

found 1 day ago

Roundtrip flight included

New York (NYC) 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. A coffee shop, a terrace, and a garden are also on offer.

Dinsmore Boutique Inn

Venable

$875

per person

Mar 27 - Mar 29

found 1 day ago

Roundtrip flight included

New York (NYC) to Charlottesville (CHO)

This bed & breakfast doesn't skimp on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. A terrace, concierge services, and wedding services are also on offer.

Top Wintergreen hotels deals

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

Roseland VA

$221 nightly

$248 total

Mar 1 - Mar 2

Total with taxes and fees

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

Pool

Hot Tub

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

Roseland VA

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This condo features laundry facilities.

Kitchen

Washer

The Modern Mountain Condo

Wintergreen Resort VA

$204 nightly

$229 total

Mar 5 - Mar 6

Total with taxes and fees

This condo features laundry facilities.

Pool

Kitchen

Wintergreen. Sunset Vista Villa - Sea of Mountains

Wintergreen Resort VA

$264 nightly

$296 total

Feb 26 - Feb 27

Total with taxes and fees

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

Pool

Kitchen

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

Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

Wintergreen Resort VA

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This condo features an outdoor pool and an indoor pool. A gym, a hot tub, and laundry facilities are also on offer.

Pool

Hot Tub

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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 $807. 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.