Wintergreen, Virginia

Vacation Rentals in Wintergreen, Virginia

Discover 123 vacation rental properties in Wintergreen. From 1 to 10 bedrooms. Average $230/night. 100% have pools.

123 verified listings Book securely on VRBO Prices updated March 2026

123 properties available

Blue Ridge Retreat with Wintergreen Advantage

Blue Ridge Retreat with Wintergreen Advantage

10 beds 10 baths
PoolA/CWiFiBalcony
$1,717/night
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White Oak 51 with Wintergreen Advantage

White Oak 51 with Wintergreen Advantage

3 beds 2 baths
PoolA/CWiFiBalcony
$319/night
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Walking Distance To Mountain Inn, Great Location For Your Mountain Getaway

Walking Distance To Mountain Inn, Great Location For Your Mountain Getaway

5 beds 3 baths
PoolA/CWiFiBalcony
$495/night
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White Oak 46 with Wintergreen Advantage

White Oak 46 with Wintergreen Advantage

3 beds 2 baths
PoolA/CWiFiBalcony
$320/night
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Beautiful 2BR/2BA - DOG FRIENDLY -- Great LOW Rates

Beautiful 2BR/2BA - DOG FRIENDLY -- Great LOW Rates

2 beds 2 baths
PoolA/CWiFiBalcony
$95/night
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Cozy Mountain Retreat with Radiant Flooring - Dog Friendly

Cozy Mountain Retreat with Radiant Flooring - Dog Friendly

1 bed 1 bath
PoolA/CWiFiBalcony
$118/night
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Orchard House with Wintergreen Advantage

Orchard House with Wintergreen Advantage

5 beds 5 baths
PoolA/CWiFiBalcony
$476/night
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Highlands 23 with Wintergreen Advantage

Highlands 23 with Wintergreen Advantage

2 beds 2 baths
PoolA/CWiFiBalcony
$250/night
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Whispering Elm with Wintergreen Advantage

Whispering Elm with Wintergreen Advantage

4 beds 4 baths
PoolA/CWiFiBalcony
$415/night
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Luxury Mountain House - May 31st Weekend still available

Luxury Mountain House - May 31st Weekend still available

3 beds 3 baths
PoolA/CWiFiBalcony
$321/night
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Fairway Woods 34 with Wintergreen Advantage

Fairway Woods 34 with Wintergreen Advantage

2 beds 2 baths
PoolA/CWiFiBalcony
$236/night
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HotTub+PoolTable+GameRoom+MovieRoom+HikeTennisPool

HotTub+PoolTable+GameRoom+MovieRoom+HikeTennisPool

5 beds 3 baths
PoolA/CWiFiBalcony
$319/night
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Overlook 48 with Wintergreen Advantage

Overlook 48 with Wintergreen Advantage

4 beds 4 baths
PoolA/CWiFiBalcony
$401/night
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Cliffs 21 with Wintergreen Advantage

Cliffs 21 with Wintergreen Advantage

1 bed 1 bath
PoolA/CWiFiBalcony
$174/night
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Nancy's Edelweiss with Wintergreen Advantage

Nancy's Edelweiss with Wintergreen Advantage

6 beds 6 baths
PoolA/CWiFiBalcony
$545/night
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Ski-In/Out, Beautiful Mountain & Valley Views

Ski-In/Out, Beautiful Mountain & Valley Views

3 beds 3 baths
PoolA/CWiFiBalcony
$251/night
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Shenandoah Ridge 07 with Wintergreen Advantage

Shenandoah Ridge 07 with Wintergreen Advantage

4 beds 4 baths
PoolA/CWiFiBalcony
$396/night
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Vistas 64 with Wintergreen Advantage

Vistas 64 with Wintergreen Advantage

2 beds 2 baths
PoolA/CWiFiBalcony
$240/night
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Highlands 05 with Wintergreen Advantage

Highlands 05 with Wintergreen Advantage

2 beds 2 baths
PoolA/CWiFiBalcony
$249/night
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Mountain-Top Retreat w/ 3 Master BR,Expansive Desks and Panoramic Window Views

Mountain-Top Retreat w/ 3 Master BR,Expansive Desks and Panoramic Window Views

5 beds 4 baths
PoolA/CWiFiBalcony
$603/night
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180 Degree Breathtaking Views

180 Degree Breathtaking Views

3 beds 3 baths
PoolA/CWiFiBalcony
$342/night
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Wintergreen Home w/ Deck - Near Skiing & Hiking!

Wintergreen Home w/ Deck - Near Skiing & Hiking!

3 beds 2 baths
PoolA/CWiFiBalcony
$182/night
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Mountaintop Lodge with Wintergreen Advantage

Mountaintop Lodge with Wintergreen Advantage

9 beds 9 baths
PoolA/CWiFiBalcony
$1,632/night
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Stoneridge 31 with Wintergreen Advantage

Stoneridge 31 with Wintergreen Advantage

1 bed 2 baths
PoolA/CWiFiBalcony
$150/night
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Highlands 02 with Wintergreen Advantage

Highlands 02 with Wintergreen Advantage

1 bed 1 bath
PoolA/CWiFiBalcony
$163/night
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Highlands 17 with Wintergreen Advantage

Highlands 17 with Wintergreen Advantage

1 bed 1 bath
PoolA/CWiFiBalcony
$166/night
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Highlands 37 with Wintergreen Advantage

Highlands 37 with Wintergreen Advantage

1 bed 2 baths
PoolA/CWiFiBalcony
$160/night
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Vistas 71 with Wintergreen Advantage

Vistas 71 with Wintergreen Advantage

1 bed 2 baths
PoolA/CWiFiBalcony
$177/night
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Stoneridge 43 with Wintergreen Advantage

Stoneridge 43 with Wintergreen Advantage

1 bed 2 baths
PoolA/CWiFiBalcony
$170/night
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Fairway Woods 22 with Wintergreen Advantage

Fairway Woods 22 with Wintergreen Advantage

2 beds 2 baths
PoolA/CWiFiBalcony
$240/night
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Fairway Woods 01 with Wintergreen Advantage

Fairway Woods 01 with Wintergreen Advantage

2 beds 2 baths
PoolA/CWiFiBalcony
$243/night
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Fairway Woods 44 with Wintergreen Advantage

Fairway Woods 44 with Wintergreen Advantage

2 beds 2 baths
PoolA/CWiFiBalcony
$244/night
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Stoneridge 26 with Wintergreen Advantage

Stoneridge 26 with Wintergreen Advantage

2 beds 2 baths
PoolA/CWiFiBalcony
$244/night
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Fairway Woods 43 with Wintergreen Advantage

Fairway Woods 43 with Wintergreen Advantage

2 beds 2 baths
PoolA/CWiFiBalcony
$240/night
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Stoneridge 77 with Wintergreen Advantage

Stoneridge 77 with Wintergreen Advantage

1 bed 2 baths
PoolA/CWiFiBalcony
$199/night
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Cliffs 07 with Wintergreen Advantage

Cliffs 07 with Wintergreen Advantage

2 beds 2 baths
PoolA/CWiFiBalcony
$232/night
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Cliffs 26 with Wintergreen Advantage

Cliffs 26 with Wintergreen Advantage

2 beds 2 baths
PoolA/CWiFiBalcony
$244/night
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Vistas 57 with Wintergreen Advantage

Vistas 57 with Wintergreen Advantage

2 beds 2 baths
PoolA/CWiFiBalcony
$244/night
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Stoneridge 29 with Wintergreen Advantage

Stoneridge 29 with Wintergreen Advantage

2 beds 2 baths
PoolA/CWiFiBalcony
$227/night
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Above The Clouds with Wintergreen Advantage

Above The Clouds with Wintergreen Advantage

4 beds 2 baths
PoolA/CWiFiBalcony
$411/night
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Stoneridge Woods 05 with Wintergreen Advantage

Stoneridge Woods 05 with Wintergreen Advantage

2 beds 2 baths
PoolA/CWiFiBalcony
$250/night
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Bull City Bungalow with Wintergreen Advantage

Bull City Bungalow with Wintergreen Advantage

4 beds 3 baths
PoolA/CWiFiBalcony
$411/night
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Fairway Woods 21 with Wintergreen Advantage

Fairway Woods 21 with Wintergreen Advantage

3 beds 2 baths
PoolA/CWiFiBalcony
$334/night
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Stoneridge 56 with Wintergreen Advantage

Stoneridge 56 with Wintergreen Advantage

2 beds 2 baths
PoolA/CWiFiBalcony
$240/night
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Stoneridge 75 with Wintergreen Advantage

Stoneridge 75 with Wintergreen Advantage

2 beds 2 baths
PoolA/CWiFiBalcony
$243/night
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Zero step entry- EV charger- 2 King suites

Zero step entry- EV charger- 2 King suites

4 beds 3 baths
PoolA/CWiFiBalcony
$345/night
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Ski-In/Ski-Out Comfy Condo

Ski-In/Ski-Out Comfy Condo

1 bed 1 bath
PoolA/CWiFiBalcony
$104/night
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Lovely Wintergreen Hideaway - 3min to Slopes

Lovely Wintergreen Hideaway - 3min to Slopes

2 beds 2 baths
PoolA/CWiFiBalcony
$142/night
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Showing 48 of 123 properties

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