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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.

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  1. Entire home
  2. Wintergreen Resort
Modern Mountain Condo w/Pool

Conveniently located within the 4-season Wintergreen Resort, this recently renovated condo offers a quiet and cozy place to stay while you take in the maginificent mountain views and enjoy endless outdoor activities, wineries, breweries, restaurants, and antique shops. Rest and recharge while you enjoy the light filled, open floor plan with a wood burning fireplace, kitchen with plenty of cabinet space and full-sized appliances for cooking. Private patio and pool access located outside unit.

$109 per night
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  1. Entire home
  2. 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.

$245 per night
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  1. Entire home
  2. Wintergreen Resort
Contemporary Mountain Home - Amazing Views

An open floor plan with high ceilings and large skylights, this amazingly engineered home will stun you with its amazing mountain views! This spacious home, with its cantilevered decks makes this perfect for any family. The large upstairs loft, adjacent to the upstairs bedrooms, offers movies, games, puzzles, and comfortable seating. Wi-Fi, Netflix, and Samsung Smart hub give plenty of entertainment options. The spacious living area and dining room have abundant seating for all.

$345 per night

Vacation rentals for every style

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Wintergreen vacation rentals

  1. Entire guesthouse
  2. Nellysford
The Nest...lovely 2 bedroom apartment in the woods
$150 per night
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  1. Entire cottage
  2. Nellysford
Pine Cottage: Hot Tub and Central to Breweries
$269 per night
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  1. Private room
  2. Nellysford
The Wintergreen Ranch -Suite
$90 per night
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  1. Entire cottage
  2. Nellysford
Rockfish Valley Cottage (High Speed Internet)
$195 per night
  1. Entire cottage
  2. Nellysford
NEW! Cottage < 10 Mi to Wineries, Skiing & Hiking
$121 per night
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  1. Entire cabin
  2. Roseland
Cabin w/ Mtn View & Firepit on Rt151 @ Base of Mtn
$343 per night
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  1. Private room
  2. Nellysford
The Wintergreen Ranch
$80 per night
  1. Entire home
  2. Nellysford
NEW! Nellysford Home ~ 10 Mi to Wintergreen Resort
$165 per night
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  1. Entire home
  2. Roseland
Charming Farmhouse in a great location!
$225 per night
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  1. Farm stay
  2. Nellysford
The Cottage at Spindle Hill: An Artist’s Farm
$232 per night
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  1. Entire cottage
  2. Nellysford
Blue-tiful & Modern - Pet Friendly
$211 per night
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  1. Entire cabin
  2. Nellysford
Rustic Cabin in the Woods
$307 per night

Wintergreen condos

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  1. Entire condo
  2. Wintergreen Resort
Panoramic Peak: Breathtaking Views
$192 per night
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  1. Entire condo
  2. Wintergreen Resort
NEW! Updated condo in the heart of Wintergreen
$100 per night
  1. Entire condo
  2. Wintergreen Resort
Point of View | Wake in the Clouds
$100 per night
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  1. Entire condo
  2. Wintergreen Resort
Amazing Blue Ridge ski-front views with Wintermint
$119 per night
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  1. Entire condo
  2. Wintergreen Resort
Best View in the Blue Ridge from Biscuit's Porch
$185 per night
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  1. Entire condo
  2. Wintergreen Resort
The Winter Fox Den
$102 per night
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  1. Entire condo
  2. Wintergreen Resort
Wintergreen Condo (Walk to Slope)
$85 per night
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  1. Entire condo
  2. Wintergreen Resort
An All Season Resort- Serenity Above the Clouds
$153 per night
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  1. Entire condo
  2. Roseland
Mountain Getaway - Unbeatable Views
$131 per night
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  1. Entire condo
  2. Wintergreen Resort
Bear's Mountain Escape
$129 per night
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  1. Entire condo
  2. Wintergreen Resort
Cozy Wintergreen Condo w/ loft -Walk to the Slopes
$102 per night
  1. Entire condo
  2. Wintergreen Resort
Tips Up: Cozy Slopeside Retreat w/ Fireplace
$117 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.


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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