Wintergreen vacation rentals
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Top-rated vacation rentals in Wintergreen
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Other great vacation rentals in Wintergreen
Condo in Wintergreen Resort
4.94 out of 5 average rating, 225 reviewsCozy, clean mountain condo- King bed, dog friendly
Sep 1 – 8
Condo in Wintergreen Resort
4.96 out of 5 average rating, 105 reviewsAll-Season 2bd/2ba next to Spa view of Golf Course
Jan 9 – 16
Condo in Wintergreen Resort
4.9 out of 5 average rating, 101 reviewsTips Up: Cozy Slopeside Retreat w/ Fireplace
Jun 14 – 21
Condo in Wintergreen Resort
4.99 out of 5 average rating, 175 reviewsCozy getaway w/ heated floors, dog friendly
Aug 9 – 16
Condo in Wintergreen Resort
4.89 out of 5 average rating, 126 reviewsCozy Comfort with a View - Wintergreen Resort
Oct 10 – 17
Condo in Wintergreen Resort
4.96 out of 5 average rating, 154 reviewsThe Modern Mountain Condo
Aug 24 – 31
Condo in Wintergreen Resort
4.99 out of 5 average rating, 141 reviews3 BR 3 BA, 2 story condo in Highlands
Aug 8 – 15
Condo in Wintergreen Resort
4.96 out of 5 average rating, 236 reviewsFive Minute Walk to Everything!
Jan 10 – 17
Wintergreen house rentals
Home in Shipman
4.88 out of 5 average rating, 117 reviewsThe Refuge at Laurel
Mar 2 – 9
Home in Wintergreen Resort
4.95 out of 5 average rating, 194 reviewsSaltbox at Wintergreen, a Modern Mountain Escape
Oct 29 – Nov 5
Home in Nellysford
4.99 out of 5 average rating, 102 reviewsGlass House | Mountain & Water Views @ Wintergreen
Nov 5 – 12
Home in Wintergreen Resort
4.97 out of 5 average rating, 153 reviewsSki-In/Ski-Out Renovated Chalet on Lower Tyro
Jun 3 – 10
Home in Roseland
4.9 out of 5 average rating, 127 reviewsCharming Farmhouse in a great location!
Apr 26 – May 3
Home in Greenwood
5.0 out of 5 average rating, 154 reviewsGorgeous Modern Mountain Home + Blue Ridge Views
Jan 7 – 14
Home in Stuarts Draft
4.85 out of 5 average rating, 264 reviewsBlackwood Air B & B
Oct 31 – Nov 7
Home in Faber
4.99 out of 5 average rating, 119 reviewsBuck Creek Lodge (2 bedrooms) Hidden in Blue Ridge
Jul 21 – 28
Ski-in/ski-out vacation rentals in Wintergreen
Condo in Wintergreen Resort
4.9 out of 5 average rating, 103 reviewsAll season 3bd/3ba ski out/in - Location & Views!
Jul 15 – 22
Condo in Wintergreen Resort
5.0 out of 5 average rating, 23 reviewsBase Camp Condo
Jun 18 – 25
Apartment in Wintergreen Resort
5.0 out of 5 average rating, 32 reviewsMountain View Nest
Aug 3 – 10
Condo in Wintergreen Resort
5.0 out of 5 average rating, 13 reviewsCozy Condo in Wintergreen Resort That Sleeps 4!
Oct 19 – 26
Condo in Wintergreen Resort
4.97 out of 5 average rating, 38 reviewsCozy little condo, near slopes.
Jun 21 – 28
Condo in Wintergreen Resort
5.0 out of 5 average rating, 31 reviewsSki-in/out: Dogs OK+Fireplace+Pack ’n play+Parking
Jul 12 – 19
Apartment in Wintergreen Resort
4.92 out of 5 average rating, 12 reviewsNew! Cozy condo in the Mountain Inn!
Aug 23 – 30
Condo in Wintergreen Resort
5.0 out of 5 average rating, 70 reviews1 bedroom condo close to hiking breweries & resort
Dec 10 – 17
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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