Wintergreen Vacation Packages 2026 from $633

Wintergreen flight + hotel vacation packages

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

Days Inn by Wyndham Charlottesville/University Area

The Meadows

$633

per person

Aug 1 - Aug 8

found 22 hours ago

Roundtrip non-stop flight included

Jacksonville (JAX) to Charlottesville (CHO)

This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Luggage storage, laundry facilities, and free newspapers are also on offer.

Lafayette Inn

$998

per person

Aug 1 - Aug 8

found 22 hours ago

Roundtrip non-stop flight included

Jacksonville (JAX) 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.

Oakhurst Inn at the University

Jefferson Park Avenue

$721

per person

Jul 27 - Jul 30

found 1 day ago

Roundtrip non-stop flight included

Wichita (ICT) 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 Doyle Hotel

Starr Hill

$663

per person

Jul 27 - Jul 30

found 1 day ago

Roundtrip non-stop flight included

Wichita (ICT) to Charlottesville (CHO)

This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. A coffee shop, a terrace, and a picnic area are also on offer.

Kimpton The Forum Hotel by IHG

UVA

$698

per person

Jul 27 - Jul 30

found 1 day ago

Roundtrip non-stop flight included

Wichita (ICT) to Charlottesville (CHO)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 10 conference rooms on site, along with the valet parking and WiFi in public areas. A garden, a communal living room, and luggage storage are also on offer.

Top Wintergreen hotels deals

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

Roseland VA

$228 nightly

$256 total

Jul 2 - Jul 3

Total with taxes and fees

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

Pool

Hot Tub

Endless Mountain Top Views from All The Way Up!

Wintergreen Resort VA

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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

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

New Build! Log Cabin with Hot Tub in Wintergreen

Wintergreen Resort VA

$900 nightly

$1,011 total

Jun 28 - Jun 29

Total with taxes and fees

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

Pool

Hot Tub

Where the Trail Ends

Wintergreen Resort VA

$186 nightly

$209 total

Jun 24 - Jun 25

Total with taxes and fees

This condo features 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

A road with vehicles, surrounded by lush green trees and hills. Direction signs for Wintergreen Mountain Village and Blue Ridge Parkway are visible.

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 $633. 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.