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Wintergreen house rentals

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Top-rated house rentals in Wintergreen

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

Home in Wintergreen Resort
Ski-In/Ski-Out Renovated Chalet on Lower Tyro
Completely renovated, 3 BR/2BA chalet, located on Lower Tyro slope, just below Tequila. Rustic decor, fully stocked kitchen, high end appliances, granite counters. Open floor plan, walls of windows, mtn views. Beautiful stone fireplace, ample comfortable seating. 2 main floor Masters, each w/King bed, TV, luxurious bedding. Loft is a dedicated kids space: 2 sets of bunks, daybed w/trundle, TV & PS4. Gas grill, 6 person hot tub. Perfect ski home to host 2 Families, or a romantic couple's getaway.
$295 per night
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Home in Wintergreen Resort
4min to Slopes: Creekside+DogOK+Ski+Hiking+PAC-MAN
5min to slopes. Creekside retreat with mountain/valley vistas amidst an aboral oasis. Child/pet/remote work-friendly w/ FAST WiFi. Unwind on classic Pac-Man arcade! Close to wineries/breweries, hiking, skiing, and horseback riding. **Sleep 11: Cal-K, Q, Bunkbed (D/D/S), Sofa bed (D) **Great Room w/ fireplace **Spacious loft/TV room with Pac-Man arcade **Large deck w/ outdoor fireplace **Smart TV every room Happy pet fee $150/pet. Outdoor pool/tennis access included. Resort access not included
$142 per night
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Home in Wintergreen Resort
Top of the Lift Mountain Getaway
Come and relax at this peaceful Mountain getaway. A perfect mix of views, hiking trails, ski on/off access, and walking distance to all of the resort facilities make this condo great for couples, friends, and families all year round. This spacious end unit is at the top of the Highlands lift and offers slope access without sacrificing the tranquil and private views. The large two bedroom layout can accommodate 6 people comfortably with a pullout sofa and air mattress if necessary. Come Visit!
$201 per night
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Wintergreen vacation rentals

Condo in Wintergreen Resort
New Condo! Hiking Trails & close Brewery & Winery
$85 per night
Condo in Wintergreen Resort
Amazing Blue Ridge ski-front views with Wintermint
$110 per night
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Condo in Wintergreen Resort
Updated Condo at the Mountain Inn
$100 per night
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Condo in Wintergreen Resort
Point of View | Wake in the Clouds
$126 per night
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Condo in Wintergreen Resort
Panoramic Peak: Wintergreen Condo with Views
$150 per night
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Rental unit in Wintergreen Resort
This Is It
$101 per night
Condo in Wintergreen Resort
A True Mountain Getaway! Ski in/Ski out!
$91 per night
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Condo in Wintergreen Resort
Cozy 1-bedroom Condo with Fireplace Near Ski Slope
$75 per night
Condo in Wintergreen Resort
Light Filled Awe-Inspiring Views from Every Window
$240 per night
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Condo in Wintergreen Resort
248 Timbers-Best Location in Wintergreen Village!
$125 per night
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Condo in Wintergreen Resort
Newly renovated/ Walk to Slopes!
$104 per night
Condo in Wintergreen Resort
Cozy Wintergreen Resort Condo: Walk to Ski Lifts!
$124 per night

Wintergreen condo rentals

Condo in Wintergreen Resort
Lovely 1-BDR condo w/indoor fireplace & ski locker
$118 per night
Condo in Wintergreen Resort
Mountaintop Getaway - Dog Friendly
$182 per night
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Condo in Wintergreen Resort
Incredible mountain views from Peak-A-Bear Den
$135 per night
Condo in Roseland
Condo in Wintergreen Resort
$121 per night
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Condo in Wintergreen Resort
Gorgeous Sunrises
$102 per night
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Condo in Wintergreen Resort
2bd/2bath at Overlook 180 degree views w/Peloton!
$157 per night
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Condo in Wintergreen Resort
Cozy remodeled studio overlooking 18th hole
$120 per night
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Condo in Wintergreen Resort
NEW! Idyllic Wintergreen Condo w/ Resort Amenities
$99 per night
Condo in Wintergreen Resort
Slope Side Gem ~ King Suite ~ Ski-In/Ski-Out
$120 per night
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Condo in Wintergreen Resort
Wintergreen Resort Escape ~ Walk to Ski Lift!
$106 per night
Condo in Wintergreen Resort
Ski-In Ski-Out Condo w/ Balcony & Slope Views!
$119 per night
Condo in Wintergreen Resort
Peaceful, renovated condo w/ free firewood
$105 per night
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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.


When is 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.


What are the 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.

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