Wintergreen Vacation Packages 2025/2026 from $480

Wintergreen flight + hotel vacation packages

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

The Doyle Hotel

Starr Hill

$480

per person

Dec 31 - Jan 4

found 22 hours ago

Roundtrip non-stop flight included

Austin (AUS) 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.

Oakhurst Inn at the University

Jefferson Park Avenue

$570

per person

Jan 9 - Jan 12

found 13 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Charlottesville (CHO)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. Self parking, a coffee shop, and a terrace are also offered.

Omni Charlottesville Hotel

North Downtown

$554

per person

Jan 9 - Jan 12

found 13 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Charlottesville (CHO)

This smoke-free hotel includes 2 restaurants, an indoor pool, and a hot tub. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and valet parking. Enjoy the gym and perks like free self parking.

English Inn of Charlottesville

The Meadows

$494

per person

Jan 9 - Jan 12

found 13 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) 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.

Dinsmore Boutique Inn

Venable

$629

per person

Jan 9 - Jan 12

found 13 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) 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.

$168 nightly

$189 total

Nov 19 - Nov 20

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

Fully Loaded 8BR in Wintergreen! Sleeps 23

Wintergreen Resort, VA

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This chalet features a gym and a hot tub. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. A sauna and laundry facilities are also provided.

Pool

Hot Tub

New Build! Log Cabin with Hot Tub in Wintergreen

Wintergreen Resort, VA

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

Pool

Hot Tub

Top of Mountain 2 BR Condo, Short Walk to scenic overlooks of the Mtns. in Fall

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This condo features laundry facilities.

Kitchen

Washer

Wow! What A View!

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

Pool

Kitchen

You deserve it all! Awesome Views, Comfy Condo & Elevator!

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

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

4.5/5(79 reviews)

Hit the slopes in Nellysford 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 Nellysford. Discover the mountain views in this family-friendly area.

Stoney Creek Golf Course

Enjoy a round of golf in Nellysford 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 $480. 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.