Wintergreen Resort, Virginia

Vacation Rentals in Wintergreen Resort, Virginia

Discover 197 vacation rental properties in Wintergreen Resort. From 1 to 7 bedrooms. Average $271/night. 100% have pools.

197 verified listings Book securely on VRBO Prices updated March 2026

197 properties available

Endless Mountain Top Views from All The Way Up!

Endless Mountain Top Views from All The Way Up!

2 beds 2 baths
PoolA/CWiFiBalcony
$236/night
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Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop

Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop

4 beds 3 baths
PoolA/CWiFiBalcony
$314/night
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Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!

Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!

3 beds 2 baths
PoolA/CWiFiBalcony
$246/night
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Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!

Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!

2 beds 1 bath
PoolA/CWiFiBalcony
$124/night
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Mountain Chalet – Panoramic Views of Blue Ridge Mountains!

Mountain Chalet – Panoramic Views of Blue Ridge Mountains!

3 beds 2 baths
PoolA/CWiFiBalcony
$132/night
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Wintergreen Resort Retreat w/ Hot Tub!

Wintergreen Resort Retreat w/ Hot Tub!

3 beds 2 baths
PoolA/CWiFiBalcony
$246/night
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An All Season Resort- Serenity Above the Clouds

An All Season Resort- Serenity Above the Clouds

2 beds 2 baths
PoolA/CWiFiBalcony
$217/night
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Perfect Getaway for Vacation or Staycation!! - New Rental!

Perfect Getaway for Vacation or Staycation!! - New Rental!

1 bed 1 bath
PoolA/CWiFiBalcony
$88/night
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Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views

1 bed 2 baths
PoolA/CWiFiBalcony
$212/night
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Wintergreen Resort Vacation Rental w/ Balcony!

Wintergreen Resort Vacation Rental w/ Balcony!

2 beds 2 baths
PoolA/CWiFiBalcony
$118/night
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Hilltop Escape At Wintergreen

Hilltop Escape At Wintergreen

5 beds 4 baths
PoolA/CWiFiBalcony
$401/night
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Luxurious ski chalet w/ fireplaces, decks, views, gourmet kitchen + and hot tub!

Luxurious ski chalet w/ fireplaces, decks, views, gourmet kitchen + and hot tub!

5 beds 4 baths
PoolA/CWiFiBalcony
$712/night
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Modern Retreat at Wintergreen

Modern Retreat at Wintergreen

3 beds 3 baths
PoolA/CWiFiBalcony
$231/night
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Amazing Views! Cabin for large groups - Hot Tub - Hiking - Pool Table - Arcade

Amazing Views! Cabin for large groups - Hot Tub - Hiking - Pool Table - Arcade

5 beds 3 baths
PoolA/CWiFiBalcony
$538/night
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Mountain house with exceptional views

Mountain house with exceptional views

4 beds 3 baths
PoolA/CWiFiBalcony
$452/night
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Hot Tub & Views | Mid Century Modern Wonder

Hot Tub & Views | Mid Century Modern Wonder

5 beds 4 baths
PoolA/CWiFiBalcony
$678/night
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Private creek, 5 minutes to slopes, under new management, pet friendly, hot tub!

Private creek, 5 minutes to slopes, under new management, pet friendly, hot tub!

4 beds 4 baths
PoolA/CWiFiBalcony
$385/night
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Cozy chalet on Wintergreen Mountain

Cozy chalet on Wintergreen Mountain

3 beds 2 baths
PoolA/CWiFiBalcony
Price on request
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Cozy 'Hillside Hideaway' in Wintergreen Resort!

Cozy 'Hillside Hideaway' in Wintergreen Resort!

3 beds 2 baths
PoolA/CWiFiBalcony
$229/night
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Savor the Summer at Oak Ledge! Trails+Tastings+Peace

Savor the Summer at Oak Ledge! Trails+Tastings+Peace

3 beds 2 baths
PoolA/CWiFiBalcony
$249/night
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Cozy Lodge with view- Wintergreen Ski Chalet - Walk to slopes & family friendly!

Cozy Lodge with view- Wintergreen Ski Chalet - Walk to slopes & family friendly!

3 beds 2 baths
PoolA/CWiFiBalcony
$278/night
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Wintergreen Resort Retreat - Walk to Slopes!

Wintergreen Resort Retreat - Walk to Slopes!

3 beds 2 baths
PoolA/CWiFiBalcony
$194/night
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The Apres Chalet - family-friendly, all-season home, steps from trails!

The Apres Chalet - family-friendly, all-season home, steps from trails!

3 beds 2 baths
PoolA/CWiFiBalcony
$370/night
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Bide-a-Wee - Hike to the trails and Walk to the slopes!

Bide-a-Wee - Hike to the trails and Walk to the slopes!

3 beds 2 baths
PoolA/CWiFiBalcony
$224/night
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Rustic Getaway with Fireplace - Walk to Slopes!

Rustic Getaway with Fireplace - Walk to Slopes!

4 beds 2 baths
PoolA/CWiFiBalcony
$323/night
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Blue Ridge Mountain Retreat in Wintergreen

Blue Ridge Mountain Retreat in Wintergreen

7 beds 3 baths
PoolA/CWiFiBalcony
$660/night
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Cozy Mountain Retreat! Short walk to slopes/hiking trails/restaurants.

Cozy Mountain Retreat! Short walk to slopes/hiking trails/restaurants.

3 beds 2 baths
PoolA/CWiFiBalcony
$184/night
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Smoky Bear Cabin

Smoky Bear Cabin

3 beds 2 baths
PoolA/CWiFiBalcony
$166/night
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5min to Ski! DogsOK+PAC-MAN+Fireplace+Pack 'n Play

5min to Ski! DogsOK+PAC-MAN+Fireplace+Pack 'n Play

3 beds 3 baths
PoolA/CWiFiBalcony
$189/night
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Springside Wintergreen Retreat w/ Hot tub & Fireplace - Great Location!

Springside Wintergreen Retreat w/ Hot tub & Fireplace - Great Location!

3 beds 2 baths
PoolA/CWiFiBalcony
$216/night
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7th Hole Chalet - New 7-person Hot Tub / Sauna / 3 Fireplaces / New VRBO!

7th Hole Chalet - New 7-person Hot Tub / Sauna / 3 Fireplaces / New VRBO!

4 beds 2 baths
PoolA/CWiFiBalcony
$382/night
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The Castor Cabin | Patio, Game Loft, Fireplace

The Castor Cabin | Patio, Game Loft, Fireplace

4 beds 3 baths
PoolA/CWiFiBalcony
$339/night
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Large deck, fire pit, hot tub overlooking golf course

Large deck, fire pit, hot tub overlooking golf course

4 beds 3 baths
PoolA/CWiFiBalcony
$423/night
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Spacious Wintergreen Resort Home w/ Hot Tub!

Spacious Wintergreen Resort Home w/ Hot Tub!

4 beds 5 baths
PoolA/CWiFiBalcony
$326/night
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Idyllic Wintergreen Condo w/ Resort Amenities

Idyllic Wintergreen Condo w/ Resort Amenities

2 beds 2 baths
PoolA/CWiFiBalcony
$105/night
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Wintergreen - Cozy Mountain Getaway! Close to Hiking Trails!

Wintergreen - Cozy Mountain Getaway! Close to Hiking Trails!

1 bed 1 bath
PoolA/CWiFiBalcony
$131/night
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Top of Mountain 2 BR Condo, Close to nearby Hiking Trails and Scenic Overlooks

Top of Mountain 2 BR Condo, Close to nearby Hiking Trails and Scenic Overlooks

2 beds 2 baths
PoolA/CWiFiBalcony
$88/night
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Cozy retreat in WG Stone Ridge Complex - Hike, Golf, Tennis and Dog-Friendly

Cozy retreat in WG Stone Ridge Complex - Hike, Golf, Tennis and Dog-Friendly

2 beds 2 baths
PoolA/CWiFiBalcony
$180/night
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Majestic Mountain View’s from The Cliffs

Majestic Mountain View’s from The Cliffs

1 bed 2 baths
PoolA/CWiFiBalcony
$151/night
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Wintergreen Condo w/ Balcony + Mountain Views!

Wintergreen Condo w/ Balcony + Mountain Views!

2 beds 2 baths
PoolA/CWiFiBalcony
$137/night
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New! 2bed/2bath condo at Wintergreen! Great mtn and valley views!

New! 2bed/2bath condo at Wintergreen! Great mtn and valley views!

2 beds 2 baths
PoolA/CWiFiBalcony
$221/night
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Wintergreen. Mountain view's for miles Sunset Vista Villa - Sea of Mountains

Wintergreen. Mountain view's for miles Sunset Vista Villa - Sea of Mountains

2 beds 2 baths
PoolA/CWiFiBalcony
$203/night
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Ski-in/Ski-out condo with mountain views

Ski-in/Ski-out condo with mountain views

2 beds 2 baths
PoolA/CWiFiBalcony
$175/night
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Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️

Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️

2 beds 2 baths
PoolA/CWiFiBalcony
$199/night
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Escape to the Blue Ridge Mountains at Wine-tergreen!

Escape to the Blue Ridge Mountains at Wine-tergreen!

2 beds 2 baths
PoolA/CWiFiBalcony
$124/night
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Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!

Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!

2 beds 2 baths
PoolA/CWiFiBalcony
$189/night
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Wintergreen Resort Vacation Rental w/ Pool Access!

Wintergreen Resort Vacation Rental w/ Pool Access!

3 beds 2 baths
PoolA/CWiFiBalcony
$180/night
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Wintergreen Resort Condo: 1 Mi to Skiing!

Wintergreen Resort Condo: 1 Mi to Skiing!

1 bed 2 baths
PoolA/CWiFiBalcony
$103/night
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Showing 48 of 197 properties

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