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Wintergreen house rentals

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Top-rated house rentals in Wintergreen

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Home in Wintergreen Resort
Kickback Condo at Wintergreen Resort on Devils Knob
Beautifully renovated getaway in Wintergreen Resort on Devil's Knob. Located at a short and convenient walk to the Wintergarden Spa, the Devils Knob golf and tennis center, and a fine dining restaurant as well as the Nature Foundation at Wintergreen. We love to relax on the quiet porch with a coffee in the morning or wine in the evening looking over the trees and the 12th fairway of Devil's Knob Golf Course. A small trail up to the golf course can be found right behind our place. It is great for walking the dogs and connects to other trails throughout the resort. If we can do anything to make your stay more enjoyable, don’t hesitate to reach out, and please kick back and relax and enjoy all that Wintergreen has to offer! Note: There is a shuttle that stops in front of Tanners Ridge for the ski slopes on the weekends. You can check the resort website or call the resort for times and details.
$186 per night
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Home in Wintergreen Resort
Mountaintop Wintergreen Resort Home w/ Deck+Views!
Escape to the mountains with this spacious 4-bed, 3-bath Virginia vacation rental home! Tucked into the Wintergreen Resort community, this house boasts a spacious deck with views of the mountains, an enclosed patio with a grill, and an upscale interior with vaulted ceilings. Enjoy year-round adventures with skiing and tubing in the winter and hiking and golfing in the summer. Thanks to resort amenities like the community pool and clubhouse, you'll never want to leave this mountaintop retreat!
$182 per night
Home in Wintergreen Resort
Peaceful 3-BR Mountain home w/Fireplace + Hot tub
Charming 3-bedroom mountain retreat at the top of Wintergreen Resort. Peaceful and private location. Relax in front of the gas fireplace, soak in the hot tub, or sit on the deck and enjoy the views. Spend your day hiking a nearby trail and enjoy visiting local restaurants, breweries, and wineries. Kitchen is fully stocked and there is a gas grill on deck. Kids will love the upstairs twin bedroom, complete with a play area with books & toys. Separate den with TV and workspace on lower level
$256 per night
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Wintergreen vacation rentals

Condo in Wintergreen Resort
Point of View | Wake in the Clouds
$131 per night
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Condo in Wintergreen Resort
The Winter Fox Den
$105 per night
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Condo in Wintergreen Resort
Newly renovated/ Walk to Slopes!
$127 per night
Cabin in Wintergreen Resort
Cozy, Updated, EV charger
$190 per night
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Condo in Wintergreen Resort
Amazing Blue Ridge ski-front views with Wintermint
$126 per night
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Condo in Wintergreen Resort
Mountaintop Getaway - Dog Friendly
$196 per night
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Cabin in Wintergreen Resort
Cozy Treeloft Cabin *Valentines Day Open!
$231 per night
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Rental unit in Wintergreen Resort
This Is It
$121 per night
Condo in Wintergreen Resort
Incredible mountain views from Peak-A-Bear Den
$146 per night
Condo in Wintergreen Resort
New! 5 minute walk to the slopes! Newly remodeled*
$135 per night
Condo in Wintergreen Resort
Panoramic Peak: Wintergreen Condo with Views
$165 per night
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Condo in Wintergreen Resort
Bear's Mountain Escape
$136 per night
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Wintergreen condo rentals

Condo in Wintergreen Resort
Wintergreen 2BR condo minutes from the slope
$115 per night
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Condo in Wintergreen Resort
2 bdrm/2 full bath Best Views of Blue Ridge Mtns.
$194 per night
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Condo in Wintergreen Resort
The Modern Mountain Condo
$118 per night
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Condo in Wintergreen Resort
Updated Condo at the Mountain Inn
$138 per night
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Condo in Wintergreen Resort
Slope Side Gem ~ King Suite ~ Ski-In/Ski-Out
$138 per night
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Condo in Wintergreen Resort
Light Filled Awe-Inspiring Views from Every Window
$246 per night
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Condo in Wintergreen Resort
King bedroom + separate bunks + walk to the slopes
$132 per night
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Condo in Roseland
Mountain Getaway - Unbeatable Views
$131 per night
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Condo in Wintergreen Resort
Panoramic views, new extended deck, cozy condo
$257 per night
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Condo in Wintergreen Resort
248 Timbers-Best Location in Wintergreen Village!
$141 per night
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Condo in Wintergreen Resort
Wintergreen Resort Escape ~ Walk to Ski Lift!
$106 per night
Condo in Wintergreen Resort
Lovely 1-BDR condo w/indoor fireplace & ski locker
$141 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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