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Wintergreen vacation rentals

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Top-rated vacation rentals in Wintergreen

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Condo in Wintergreen Resort
Light Filled Awe-Inspiring Views from Every Window
There is something magical about this place. From the breathtaking sunrises to the sleek, modern lines of our furnishings to the romantic , unencumbered view from our cozy living room, our location is designed to help you recharge and reconnect. Imagine working remotely while watching an amazing sunrise. From the Hiker, Wine Lover, Explorer, Golfer, Skier, this location has something for everyone. Located on the ground floor, our unit gives you easy access to the sweeping backyard that allows y
$182 per night
Condo in Wintergreen Resort
Amazing Blue Ridge ski-front views with Wintermint
Experience one of the best year-round locations at Wintergreen in this 1 bedroom/1 bath, slope-front 1.5 level condo in the heart of the Wintergreen Resort! This incredible spot offers a quiet and cozy getaway for 2 guests seeking adventure or nothing at all. Enjoy the ability to ski-in/out from the property during the wintertime and explore the hiking trails during the summer. It's a short walk to the Mountain Inn (next door), 3 restaurants/bars, shopping, Starbucks, and outdoor activities.
$99 per night
Cottage in Afton
Couples Getaway, W/ King bed,heart of RT 151
The Cottage is conveniently located along the Brew Ridge Trail. Sit on your patio and watch the sun set over Humpback rock and the Blue Ridge Mountains. Amazing location that’s set right in the middle of all the breweries. Spacious 6 acre farm with Route 151 road frontage. This handsome cottage is the perfect romantic get-a-way. Enjoy WiFi, air con, parking, self check-in and all the amenities you need to feel at home. Picturesque mountain views and beautifully landscaped grounds.
$110 per night

Wintergreen house rentals

Home in Wintergreen Resort
Ski-In/Ski-Out Renovated Chalet on Lower Tyro
$295 per night
Home in Greenwood
Gorgeous Modern Mountain Home + Blue Ridge Views
$450 per night
Home in Wintergreen Resort
The Blue Ridge Eagles Nest. Summit of Wintergreen
$164 per night
Home in Wintergreen Resort
Saltbox at Wintergreen, a Modern Mountain Escape
$199 per night
Home in Faber
Buck Creek Lodge (2 bedrooms) Hidden in Blue Ridge
$195 per night
Home in Roseland
Charming Farmhouse in a great location!
$220 per night
Home in Nellysford
Winery & Brew Trail, Hiking, Fire Pit, & Ski
$122 per night
Home in Wintergreen Resort
The Cozy Cottage | Mountain views at Wintergreen
$306 per night
Home in Wintergreen Resort
Bear's Mountain Escape
$102 per night
Home in Wintergreen Resort
Top of the Lift Mountain Getaway
$90 per night
Home in Nellysford
Cozy Hideaway House in the Woods
$206 per night
Home in Wintergreen Resort
Springside home w/ hot tub in Wintergreen Resort
$197 per night

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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