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Wintergreen house rentals

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Top-rated house rentals in Wintergreen

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Home in Wintergreen Resort
Ski-In/Ski-Out Renovated Chalet on Lower Tyro
Completely renovated, 3 BR/2BA chalet, located on Lower Tyro slope, just below Tequila. Rustic decor, fully stocked kitchen, high end appliances, granite counters. Open floor plan, walls of windows, mtn views. Beautiful stone fireplace, ample comfortable seating. 2 main floor Masters, each w/King bed, TV, luxurious bedding. Loft is a dedicated kids space: 2 sets of bunks, daybed w/trundle, TV & PS4. Gas grill, 6 person hot tub. Perfect ski home to host 2 Families, or a romantic couple's getaway.
$238 per night
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Home in Wintergreen Resort
HotTub+PoolTable+Shuffleboard+HikeGolfTennisPool
Sweeping views year round. Retreats, romantic weekends or adventurous getaways. Close to wineries, breweries, farmers market, and walking distance to three great hiking trails. Sleeps 16: K, K, Q, 2 DBL,4 twin, 1PO ★Dogs OK ★2,714sqft ★HOT TUB for 7 ★Sound system ★2-Story vaulted ceiling, gas fireplace, 60"TV ★Dining table for 6 + breakfast bar ★Workspace w/ FAST Wi-Fi ★Shuffleboard ★Pool Table Seasonal pool/tennis. Resort access not included. Pet fee $150. 8min walk or 3min drive to slopes.
$281 per night
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Home in Wintergreen Resort
Post & Beam Beauty !
This special place at Wintergreen Resort is only .8 mi to ski, board or snow tube. Relax in a modern post & beam styled home that is truly unique, complete with an office area, 3 bedrooms, sleeping loft, hang out loft, 3 full baths, a wood stove to create those warm & cozy evenings & deck fire-pit. Wintergreen Resort is adjacent to the Blue Ridge Parkway, famous Rt 151 w/breweries, cideries, wineries & dining. Hike/explore nearby lakes & parks. Enjoy nature & views in a bright & cozy space
$214 per night
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Wintergreen vacation rentals

Condo in Wintergreen Resort
New Condo! Hiking Trails & close Brewery & Winery
$94 per night
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Condo in Wintergreen Resort
2nd-Floor Condo w/ Community Pool Access!
$106 per night
Condo in Wintergreen Resort
King bedroom, separate bunks, walk to everything
$105 per night
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Condo in Wintergreen Resort
Cozy 1-bedroom Condo with Fireplace Near Ski Slope
$87 per night
Condo in Wintergreen Resort
Incredible mountain views from Peak-A-Bear Den
$110 per night
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Condo in Wintergreen Resort
1 min walk to the pool - 1-BR in Laurelwood
$117 per night
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Condo in Wintergreen Resort
Lovely 1-BDR condo w/indoor fireplace & ski locker
$105 per night
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Condo in Wintergreen Resort
Cozy and clean two bedroom condo.
$105 per night
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Condo in Wintergreen Resort
A True Mountain Getaway! Ski in/Ski out!
$99 per night
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Condo in Wintergreen Resort
Newly renovated/ Walk to Slopes!
$93 per night
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Condo in Wintergreen Resort
Dog/Kid-Friendly: Fireplace+Hike/Golf/Tennis/Pool
$79 per night
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Condo in Wintergreen Resort
Five Minute Walk to Everything!
$120 per night
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Weekend vacation rentals in Wintergreen

Condo in Wintergreen Resort
Amazing Blue Ridge ski-front views with Wintermint
$112 per night
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Condo in Wintergreen Resort
Updated Condo at the Mountain Inn
$99 per night
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Loft in Wintergreen Resort
A Loft For All Seasons Ski In/Ski Wintergreen Inn
$93 per night
Condo in Wintergreen Resort
All-Season 2bd/2ba next to Spa view of Golf Course
$145 per night
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Rental unit in Wintergreen Resort
This Is It
$102 per night
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Chalet in Wintergreen Resort
Brown Bear Lodge, walk to the slopes!
$137 per night
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Condo in Wintergreen Resort
All season 3bd/3ba ski out/in - Location & Views!
$164 per night
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Rental unit in Wintergreen Resort
Cozy Wintergreen condo-4 season!
$114 per night
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Condo in Wintergreen Resort
Ski In & Ski Out Condo - Heart of Wintergreen
$109 per night
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Condo in Wintergreen Resort
Tips Up: Cozy Slopeside Retreat w/ Fireplace
$98 per night
Private room in Wintergreen Resort
Luxurious MountainTop Retreat - Wintergreen Resort
$86 per night
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Condo in Wintergreen Resort
248 Timbers-Best Location in Wintergreen Village!
$125 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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