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Vacation rentals in Wintergreen

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Top-rated vacation rentals in Wintergreen

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The Wintergreen Ranch -Suite
SUPERHOST
Private room · 4 guests · 1 bed · 1.5 shared baths
The Wintergreen Ranch -SuiteThe Wintergreen Ranch is located in the heart of Nellysford with 360 degree views in a quiet nestled neighborhood. Safe area for running or hiking , we are located minutes from Devils Backbone and Wild Wolf Brewery. Also Bold Rock Cidery, 10 minute ride up the mountain to Wintergreen Resort for skiing. Breakfast is included with your stay and Chef Mark and Baker Kelly will provide a Gourmet Fest for you to enjoy.
NEW! Starry Cabin in heart of Nellysford
Entire cabin · 7 guests · 3 beds · 2 baths
NEW! Starry Cabin in heart of NellysfordWelcome to Starry Cabin-your relaxing retreat in the country! Come kick back in our log cabin home in the heart of Nellysford off 151. Nestled in foothills of the Blue Ridge mountains & wine country, home sits in tranquil golf course community of Stoney Creek. Wineries/Breweries/Cideries/restaurants all 5-15 min drive. Many year round activities for the whole family like golf, walk/running paths, biking, hiking, fishing. Wintergreen, Crabtree Falls, Skyline Drive, Blue Ridge Pkwy & AT nearby.
Grace's Place Petite Retreat C  Perfect location!
SUPERHOST
Tiny house · 4 guests · 2 beds · 1 bath
Grace's Place Petite Retreat C Perfect location!Stay in an actual 380 square foot Tiny House conveniently located at the end of the Nelson County Brew Trail, less than a mile from the Devil’s Backbone. This beautifully finished tiny home sleeps 4 people with a private bedroom and a comfortable queen sized sleeper sofa. We are situated on 65 acres of private land with beautiful views of the Blue Ridge and hiking trails on site for you to enjoy!

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Other great vacation rentals in Wintergreen

SUPERHOST
  1. Entire residential home
  2. Nellysford
The "Small" House
$248 per night
SUPERHOST
  1. Farm stay
  2. Nellysford
The Cottage at Spindle Hill Farm
$273 per night
SUPERHOST
  1. Entire guest suite
  2. Nellysford
Welcome to the Porch, Woodland Cottage Suite
$140 per night
SUPERHOST
  1. Private room
  2. Nellysford
The Wintergreen Ranch
$80 per night
SUPERHOST
  1. Entire residential home
  2. Nellysford
Spruce Creek Abode
$210 per night
SUPERHOST
  1. Entire residential home
  2. Nellysford
The GranJan in the Rockfish Valley
$256 per night
SUPERHOST
  1. Entire residential home
  2. Roseland
Charming Farmhouse in a great location!
$225 per night
SUPERHOST
  1. Entire residential home
  2. Nellysford
5 BR Wintergreen House w/ Game Room, 75” TV & Bar
$329 per night
SUPERHOST
  1. Entire residential home
  2. Nellysford
High View Haven near Wintergreen Resort
$614 per night
SUPERHOST
  1. Entire residential home
  2. Nellysford
Glass House | Mountain & Water Views @ Wintergreen
$611 per night
SUPERHOST
  1. Entire residential home
  2. Nellysford
FROGSONG NOW, MORE THAN EVER! Peace & Quiet
$380 per night
SUPERHOST
  1. Entire vacation home
  2. Nellysford
Magnificent Estate on 14 Acres in the Mountains
$999 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.


How do I get around Wintergreen?

The closest airport to Wintergreen is Eagle’s Nest Airport (W13) in Waynesboro, just over 30 minutes to the northwest, but Charlottesville-Albemarle Airport (CHO), about 45 minutes to the northeast, and Shenandoah Valley Regional Airport (SHD), about 50 minutes to the north, will offer more options. The closest major airports are Richmond International Airport (RIC), about an hour and 45 minutes to the east and Dulles International Airport (IAD), about two and a half hours to the northeast. For regional train travel, there are stops in Charlottesville, about 40 minutes to the northeast; Staunton, about 40 minutes to the northwest; and Lynchburg, about 50 minutes to the south. If you’re planning on exploring the region, driving will be the most convenient option, although there are a few private transportation options.


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 — 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.