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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
Incredible mountain views from Peak-A-Bear Den
Peak-A-Bear Den offers guests a comfortable mountain retreat with breathtaking views of the Blue Ridge Mountains. Our 850 sq. ft, 1 bedroom 2 bath condo provides a high end decorated space for up to 4 guests. The ideal location offers panoramic views of the mountains with easy access to area amenities including skiing, wineries/breweries/distilleries, hiking and more. Enjoy sunrise coffee, curl up with a good book by the fire, take to the lifts and explore all Wintergreen has to offer.
$110 per night
Condo in Wintergreen Resort
Mountain Window: Balcony+55" TV+Hike/Tennis/Pool
What a view! Walk to trails. Activities are endless: apple picking, breweries/wineries, hiking, lake, horseback riding, golf, tennis, skiing... Take a peaceful morning walk on path across the street from the cabin. One mile to Founder's Overlook and amazing sunrises! ★Balcony w/ incredible view ★Comfortably sleeps 4: K and Q ★Fireplace ★FAST Wi-Fi ★3 Smart TVs w/ Hulu, Disney+, ESPN Outdoor pool/tennis access included. 3min drive to slopes.
$132 per night
Condo in Wintergreen Resort
Point of View | Wake in the Clouds
Jaw dropping views of the Blue Ridge Mountains in this cozy 1 bed | 2 bath condo in Wintergreen . A bright and welcoming feel will let you settle in and relax in no time. This space is perfect for couples with up to 2 small children, and the adventurous souls who wants to wake up in the clouds and have easy access to the trails. Please be sure the read below for Wintergreen Resort Amenities rules and accessibility during your stay.
$122 per night

Wintergreen house rentals

Home in Wintergreen Resort
Ski-In/Ski-Out Renovated Chalet on Lower Tyro
$251 per night
Home in Wintergreen Resort
Four Season Mountain House
$130 per night
Home in Wintergreen Resort
Ski-in/out condo with year-round mountain views
$179 per night
Home in Wintergreen Resort
Top of the Lift Mountain Getaway
$99 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.

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