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Vacation rentals in Wintergreen

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Vacation rentals for every style

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Popular amenities for Wintergreen vacation rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Stay near Wintergreen's top sights

Bold Rock Hard Cider109 locals recommend
Basic Necessities42 locals recommend
Blue Ridge Pig31 locals recommend
Rockfish Valley Foundation Natural History Center7 locals recommend
Rockfish Valley Trail Parking Lot10 locals recommend
Wintergreen True Value Hardware7 locals recommend

Other great vacation rentals in Wintergreen

Guest favorite
Bungalow in Waynesboro
4.9 out of 5 average rating, 269 reviews

Cheerful 2 bd bungalow with HOT TUB! Pet friendly!

Top guest favorite
An outdoor seating area is presented on a wooden deck, featuring a dark wicker furniture set with beige cushions. A square glass-top table is situated among the sectional sofa and armchairs, all surrounded by a lush green landscape and sunlight.
Home in Charlottesville
5 out of 5 average rating, 23 reviews

Casa Crozet

Superhost
Cabin in Crozet
4.86 out of 5 average rating, 101 reviews

#4 Cabin Near Wineries, Breweries, UVA, & Hiking

Superhost
Condo in Wintergreen Resort
4.88 out of 5 average rating, 163 reviews

Wander Lodge: Golf, Spa, Wine, or just a getaway

Guest favorite
A hot tub is positioned in the foreground, showcasing bubbling water. In the background, a vibrant pink tree stands against a clear blue sky, surrounded by green grass and blooming shrubs. String lights are suspended above, enhancing the outdoor space.
Barn in North Garden
4.88 out of 5 average rating, 197 reviews

Barn Suite, Mountain View's & Hot tub! Pets OK

Top guest favorite
Home in Nellysford
5 out of 5 average rating, 30 reviews

Foxy Retreat Stoney Creek/ Wintergreen Golf/ Ski

Guest favorite
A cozy outdoor patio features a small table set for two, surrounded by greenery. Warm string lights create a gentle glow above, illuminating the space. Sliding glass doors lead into the interior, with soft curtains allowing for natural light.
Condo in Wintergreen Resort
4.98 out of 5 average rating, 50 reviews

Cozy little condo, near slopes.

Top guest favorite
Home in Afton
5 out of 5 average rating, 33 reviews

Retreat at Mallory Creek

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Your guide to Wintergreen

Welcome to Wintergreen

Sitting on the eastern slopes of the Blue Ridge Mountains — which are part of the Appalachian Mountains — is the Virginia destination of Wintergreen. Located about 40 minutes southeast of Charlottesville, the area is known for its wide-ranging elevations, from the deep valley floors to the majestic mountaintops. The community was built as a golf destination in the spring and summer and as a winter sports hub in the snowy months, making it the perfect mountain escape any time of year.

The best time to stay in a vacation rental in Wintergreen

The weather in Wintergreen doesn’t just depend on the time of year. It also hangs on elevation. The valley sits about 700 feet above sea level, giving it approximately the same climate as Charlottesville, adorned with a little mountain breeze, while the top of the mountain is a whopping 3,850 feet, meaning that the temperatures are typically 12 to 15 degrees Fahrenheit lower than in the valley. Daytime highs to evening lows can also swing about 20 degrees Fahrenheit. While the snow-covered slopes in the winter attract skiers and snowboarders to the area’s vacation house rentals — especially from December through March — summer has its own draws, with events such as the Wintergreen Music Festival and Academy and Old Wintergreen Day, celebrating the community. Craft shows also take place during Memorial Day Weekend, Fourth of July, Labor Day, and Oktoberfest.

Top things to do in Wintergreen

Outdoor Sports

From the beginning, Wintergreen was conceived as a year-round destination, with its golf resort opening in 1988 and its ski facilities opening a year later. Nowadays, those teeing off have a choice of two courses at Devils Knob and Stoney Creek, while skiers and snowboarders can choose from 24 trails, including 14 that are lit for night skiing. There’s also a 900-foot snow tubing hill and an ice skating rink that can hold 60 skaters. Other activities include tennis, boating, biking, hiking, ziplining, and flying high on the floating trampoline.

Rockfish Valley Trails

Five trails run through the south fork of Rockfish River and Reid’s Creek with six miles of pathways that are popular with hikers and birdwatchers. There are parking lots at the Rockfish River trailhead, as well as the 35-acre Spruce Creek Park, the only public park in Nelson County.

Skyline Drive at Shenandoah National Park

From Wintergreen, it’s about a 20-minute drive to the northern entrance of the Blue Ridge Parkway, Rockfish Gap Entrance Station. This is also the southernmost entrance point to the national park’s historic Skyline Drive, where the 105-mile stretch has its final mile marker near Waynesboro. From there, the scenic road stretches north along the crest of the Blue Ridge Mountains up to the mile marker 0 in Front Royal.

Destinations to explore

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