Wintergreen vacation rentals

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Popular amenities for Wintergreen vacation rentals

Wintergreen condo rentals

Guest favorite

Condo in Wintergreen Resort

5.0 out of 5 average rating, 104 reviews

Mountaintop Getaway - Dog Friendly

Jun 30 – Jul 7

$196 per night
Guest favorite

Condo in Wintergreen Resort

4.99 out of 5 average rating, 175 reviews

Cozy getaway w/ heated floors, dog friendly

Aug 10 – 17

$112 per night
Guest favorite

Condo in Wintergreen Resort

4.94 out of 5 average rating, 222 reviews

Cozy, clean mountain condo- King bed, dog friendly

Sep 11 – 18

$98 per night
Guest favorite

Condo in Wintergreen Resort

4.89 out of 5 average rating, 126 reviews

Condo - King Master Suite - Wintergreen Resort

Sep 16 – 23

$122 per night
Guest favorite

Condo in Wintergreen Resort

4.98 out of 5 average rating, 120 reviews

Slope side+Panoramic Mountain Views!

May 14 – 21

$158 per night
Guest favorite

Condo in Wintergreen Resort

4.96 out of 5 average rating, 155 reviews

Ski-in/Ski-out Wintergreen Highlands Condo -Views!

Jan 3 – 10

$157 per night
Guest favorite

Condo in Wintergreen Resort

4.99 out of 5 average rating, 141 reviews

3 BR 3 BA, 2 story condo in Highlands

Dec 25 – Jan 1

$285 per night
Guest favorite

Condo in Wintergreen Resort

4.89 out of 5 average rating, 190 reviews

Light Filled Awe-Inspiring Views from Every Window

Jan 29 – Feb 5

$192 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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