Wintergreen Vacation Packages 2026 from $652

Wintergreen flight + hotel vacation packages

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

Little Mod Hotel at the University

Venable

$652

per person

Apr 12 - Apr 17

found 20 hours ago

Roundtrip flight included

Chicago (ORD) 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.

Dinsmore Boutique Inn

Venable

$1,026

per person

May 29 - Jun 2

found 16 hours ago

Roundtrip flight included

Chicago (ORD) 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.

Oakhurst Inn at the University

Jefferson Park Avenue

$814

per person

Apr 25 - Apr 28

found 1 day ago

Roundtrip non-stop flight included

Omaha (OMA) 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.

The Draftsman, Charlottesville, University, Autograph Collection Hotel

10th and Page

$1,031

per person

May 29 - Jun 2

found 16 hours ago

Roundtrip flight included

Chicago (ORD) to Charlottesville (CHO)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A library, express check-in, and express check-out are also on offer.

Virginia Guesthouse At University Of Virginia

Lewis Mountain

$1,024

per person

May 29 - Jun 2

found 16 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.

Top Wintergreen hotels deals

The Modern Mountain Condo

Wintergreen Resort VA

$204 nightly

$229 total

Mar 11 - Mar 12

Total with taxes and fees

This condo features laundry facilities.

Pool

Kitchen

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

Roseland VA

Get rates

This condo features laundry facilities.

Kitchen

Washer

New Build! Log Cabin with Hot Tub in Wintergreen

Wintergreen Resort VA

Get rates

Enjoy free WiFi, laundry facilities, and patios. Popular attractions Wintergreen Resort and Raven's Roost Overlook are located nearby.

Pool

Hot Tub

WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS

Wintergreen Resort VA

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This condo features laundry facilities.

Kitchen

Washer

Wintergreen. Sunset Vista Villa - Close to the ski slopes

Wintergreen Resort VA

$242 nightly

$272 total

Mar 12 - Mar 13

Total with taxes and fees

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

Pool

Kitchen

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

Roseland VA

$220 nightly

$247 total

Mar 12 - Mar 13

Total with taxes and fees

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

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 $652. 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.