Search resultsOver 1,000 homes

Apartment in Wintergreen Resort
Endless Mountain Top Views from All The Way Up!
3 beds
Dec 1 – 6
$172 per night
Superhost
Condo in Wintergreen Resort
2BR/2BA Updated, Modern Condo!
4 beds
Dec 1 – 6
$54 per night, originally $73
Superhost
Condo in Wintergreen Resort
Five Minute Walk to Everything!
5 beds
Dec 4 – 9
$84 per night, originally $105
Superhost
Cottage in Staunton
The Firefly Cottage
1 queen bed
Dec 1 – 6
$101 per night, originally $128
Superhost
Guesthouse in Afton
Nelson 151, Wine, Brew trail, Hike, Mountain Views
4 beds
Dec 1 – 7
$166 per night
Superhost
Cabin in Afton
Wes Cabin - Great space for a getaway from home!
2 queen beds
Dec 5 – 10
$125 per night
Superhost
Home in Charlottesville
Bluebird Bungalow in Frye Spring- 2 bed, 1 bath
2 queen beds
Dec 1 – 6
$116 per night, originally $145
Superhost
Condo in Wintergreen Resort
The Winter Fox Den
2 beds
Dec 11 – 17
$80 per night, originally $99
Superhost
Condo in Wintergreen Resort
Cozy 1-bedroom Condo with Fireplace Near Ski Slope
1 queen bed
Dec 1 – 6
$59 per night, originally $79
Home in Wintergreen Resort
Pet-friendly! Chef's Kitchen+Ski+Hiking+FAST Wi-Fi
5 beds
Dec 1 – 6
$131 per night
Superhost
Vacation home in Wintergreen Resort
*NEW* Wintergreen Retreat- 3 min walk to slopes.
3 beds
Dec 1 – 8
$125 per night
Condo in Wintergreen Resort
Best View in the Blue Ridge from Biscuit's Porch
1 queen bed
Dec 4 – 9
$150 per night
Superhost
Condo in Wintergreen Resort
Mountaintop Getaway - Dog Friendly
2 beds
Dec 4 – 9
$175 per night
Superhost
Condo in Wintergreen Resort
Point of View | Wake in the Clouds
1 bed
Dec 4 – 9
$150 per night
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Cabin in Wintergreen Resort
Cozy Treeloft Cabin
5 beds
Jan 8 – 13
$298 per night
Superhost
Condo in Wintergreen Resort
Amazing Blue Ridge ski-front views with Wintermint
1 king bed
Dec 1 – 6
$114 per night
Superhost
Cottage in Wintergreen Resort
Epic Views! Chef's Kitchen+Office+Ski+Hiking+Wi-Fi
5 beds
Dec 12 – 18
$169 per night
Superhost
Home in Wintergreen Resort
The Mountain Lodge On Devil's Loop
7 beds
Dec 1 – 6
$147 per night, originally $182
Superhost
Chalet in Wintergreen Resort
Quaint chalet near market sleeps 4-6 pet friendly
2 beds
Dec 1 – 6
$98 per night
Condo in Wintergreen Resort
Sunset Vista Villa - Minutes to the Slopes
2 king beds
Dec 5 – 10
$144 per night, originally $186
Superhost