Wintergreen Vacation Packages 2025 from $561

Wintergreen flight + hotel vacation packages

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

Comfort Inn Monticello

per person

Aug 8 - Aug 10

found 1 day ago

Roundtrip non-stop flight included

Phoenix (PHX) to Charlottesville (CHO)

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. There's a seasonal outdoor pool on site, and a 24-hour front desk and express check-out are also provided.

Kimpton The Forum Hotel by IHG

UVA

per person

Aug 8 - Aug 10

found 1 day ago

Roundtrip non-stop flight included

Phoenix (PHX) 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.

Dinsmore Boutique Inn

Venable

per person

Aug 8 - Aug 10

found 1 day ago

Roundtrip non-stop flight included

Phoenix (PHX) to Charlottesville (CHO)

This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free cooked-to-order breakfast each morning. A terrace and wedding services are also provided.

English Inn of Charlottesville

The Meadows

per person

Aug 8 - Aug 10

found 1 day ago

Roundtrip non-stop flight included

Phoenix (PHX) to Charlottesville (CHO)

This hotel features an indoor pool and a 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.

Inn and Tavern at Meander

per person

Aug 8 - Aug 10

found 1 day ago

Roundtrip non-stop flight included

Phoenix (PHX) to Charlottesville (CHO)

A restaurant, free self parking, and a terrace are among this bed & breakfast's amenities. WiFi in public areas is free. A garden, a snack bar/deli, and a lobby fireplace are also on offer.

Top Wintergreen hotels deals

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

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This vacation home features an outdoor pool and a hot tub. Laundry facilities and barbecue grills are also provided.

Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!

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Ski-in/ski-out access and a hot tub are featured at this smoke-free vacation home. There's a gym on site, and laundry facilities and barbecue grills are also offered.

Blue Ridge Mountain Retreat in Wintergreen

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A gym is featured at this vacation home, along with laundry facilities.

Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!

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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.

Cozy 6-bedroom cabin in Wintergreen Resort

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This cabin features laundry facilities.

Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!

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A hot tub is featured at this vacation home, along with barbecue grills.

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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 $561. 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.