Airbnb, Vacation Rentals in Wintergreen, VA
Compare 1,498 available vacation home properties, starts from $31
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Airbnb, Vacation rentals and hotel deals in Wintergreen, VA
Wintergreen Resort Studio w/ Deck & Ski-out Access
Apartment · 2 Guests · 1 Bedroom
$137 /night
10 (6 reviews)
Winter Retreat at Oak Ledge: Ski Tips & Cozy Sips
Cabin · 2 Guests · 1 Bedroom
$301 /night*
9.8 (17 reviews)
Condo at Fairway Woods, perfect home base for ski season! ☃️🏂
Holiday home · 2 Guests · 1 Bedroom
$283 /night*
9.6 (101 reviews)
Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!
Condo · 2 Guests · 1 Bedroom
$283 /night*
9.0 (154 reviews)
Residence Inn Waynesboro
Hotel · 2 Guests · 1 Bedroom
$189 /night
9.8 (44 reviews)
House / hot tub/pet friendly
Holiday home · 2 Guests · 1 Bedroom
$175 /night*
10 (63 reviews)
Murphy’s Place 2-bedroom apartment near hiking skiing wineries and breweries.
Apartment · 2 Guests · 1 Bedroom
$150 /night*
10 (12 reviews)
Freshwater Field Cabin
Cabin · 2 Guests · 1 Bedroom
$200 /night*
9.8 (16 reviews)
Fleetwood (c. 1809) - A renovated landmark
Holiday home · 2 Guests · 1 Bedroom
$190 /night*
9.8 (41 reviews)
Devil's Knob Mtn. condo on golf course with views of Shenandoah Valley
Condo · 2 Guests · 1 Bedroom
$207 /night*
9.8 (98 reviews)
Blue Ridge Mountains, Hiking, Skiing, Fishing, Mountain Air, Breweries, Wineries
Cottage · 2 Guests · 1 Bedroom
$175 /night*
10 (16 reviews)
Cozy Cabin with private HOT TUB!
Cabin · 2 Guests · 1 Bedroom
$300 /night*
10 (2 reviews)
NEW! Beautiful house with Fire Pit!
Holiday home · 2 Guests · 1 Bedroom
$258 /night*
10 (12 reviews)
Blue Ridge Retreat: Your Cozy Mountain Getaway
Condo · 2 Guests · 1 Bedroom
$167 /night*
8.4 (259 reviews)
Comfort Inn Waynesboro
Hotel · 2 Guests · 1 Bedroom
$102 /night
10 (43 reviews)
Afton Apartment on Nelson 151: Close to Wineries!
Apartment · 2 Guests · 1 Bedroom
$143 /night*
8.6 (20 reviews)
Cabin Creekwood
Bungalow · 2 Guests · 1 Bedroom
$115 /night
9.8 (98 reviews)
Condo at Wintergreen! The best Valley and Resort Views! 🏔️🗻
Condo · 2 Guests · 1 Bedroom
$283 /night*
10 (7 reviews)
Newly remodeled farmhouse on 151 Trail in Nelson County
Holiday home · 2 Guests · 1 Bedroom
$299 /night*
9.6 (35 reviews)
Next Door to Veritas Vineyard Charlottesville-Afton Mountain Virginia
Holiday home · 2 Guests · 1 Bedroom
$228 /night*
How Does The Amenity Info Looks Like at Wintergreen, VA?
Top Rental Amenities in Wintergreen, VA
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Which Price Range Is Considered As A Good Deal in Wintergreen, VA Area?
Vacation House & Condo Rental Price Information in Wintergreen, VA
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Which Accommodations Should I Pick in Wintergreen, VA?
Rental Property Types in Wintergreen, VA
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How Many Accommodations Are Not Pets Friendly in Wintergreen, VA?
Percentage of Pet Friendly Rental Properties in Wintergreen, VA
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What Are The Must-Visit Places in Wintergreen, VA?
Tourist Attractions In Wintergreen, VA
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Airports Options in Wintergreen, VA
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Other Vacation Rentals Ideas
Airbnb, Vacation House with Fireplace in Wintergreen, VA
Fireplace
9.6 (28 reviews)
Serene Hideaway with Views, 1 Mi to Hike & Ski!
Cabin · 2 Guests · 1 Bedroom
$370 /night*
Fireplace
8.0 (1 review)
Mountain Escape at Wintergreen Resort
Chalet · 2 Guests · 1 Bedroom
$350 /night*
Fireplace
10 (7 reviews)
Newly remodeled farmhouse on 151 Trail in Nelson County
Holiday home · 2 Guests · 1 Bedroom
$299 /night*
Airbnb, Vacation Condo with Pool in Wintergreen, VA
Pool
10 (13 reviews)
Walk to Ski! Dogs OK+Hiking+Pack 'n Play+Fireplace
Condo · 2 Guests · 1 Bedroom
$178 /night*
Pool
10 (79 reviews)
2 Bdrm Condo - Mountain Views, Great for Skiing & Pet Friendly
Condo · 2 Guests · 1 Bedroom
$195 /night*
Pool
10 (49 reviews)
Easy walk to the Mountain Inn & slopes. Dog friendly for fee.
Condo · 2 Guests · 1 Bedroom
$137 /night*
Airbnb, Vacation Condo with Full Kitchen in Wintergreen, VA
Full Kitchen
9.6 (93 reviews)
Fabulous Views at a lovely Ridge Top Condo!
Condo · 2 Guests · 1 Bedroom
$250 /night*
Full Kitchen
9.6 (101 reviews)
Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!
Condo · 2 Guests · 1 Bedroom
$283 /night*
Full Kitchen
10 (161 reviews)
Book Now for Fall and Winter....Awesome Views and 5-Star Amenities
Condo · 2 Guests · 1 Bedroom
$390 /night*
* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.