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Wintergreen Vacation Rentals

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136 rentals in Wintergreen.
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Views On The Shenandoah Valley And Minutes To The Slopes., vacation rental in Wintergreen

Views On The Shenandoah Valley And Minutes To The Slopes.

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Golf Front Home with Member Access to Devil's Knob and All Resort Amenities, vacation rental in Wintergreen

Golf Front Home with Member Access to Devil's Knob and All Resort Amenities

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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True Ski In/Out! Step off deck onto beginner slopes!, vacation rental in Wintergreen

True Ski In/Out! Step off deck onto beginner slopes!

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Wintergreen Home w/ Deck - Near Skiing & Hiking!, vacation rental in Wintergreen

Wintergreen Home w/ Deck - Near Skiing & Hiking!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Condo at Wintergreen! Join us for your winter vacation!, vacation rental in Wintergreen

Condo at Wintergreen! Join us for your winter vacation!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Ski-In Ski-Out Wintergreen Condo w/Balcony, vacation rental in Wintergreen

Ski-In Ski-Out Wintergreen Condo w/Balcony

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Large and Luxurious Exec 5BR House, vacation rental in Wintergreen

Large and Luxurious Exec 5BR House

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Walk to slopes/Mountain Inn, vacation rental in Wintergreen

Walk to slopes/Mountain Inn

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Heavenly view from the top of the Mountain.  Pet Friendly. Come relax!, vacation rental in Wintergreen

Heavenly view from the top of the Mountain. Pet Friendly. Come relax!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Wintergreen Five Star Rated One Bedroom Condo at affordable prices., vacation rental in Wintergreen

Wintergreen Five Star Rated One Bedroom Condo at affordable prices.

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Family Time, Ski/tube, Hike, Swimming, Parking Pass, Great Restaurants & more!, vacation rental in Wintergreen

Family Time, Ski/tube, Hike, Swimming, Parking Pass, Great Restaurants & more!

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Mtn. View, Steps to Slopes, Member Guest Pass, 25% off mid-week**, vacation rental in Wintergreen

Beautiful Mtn. View, Steps to Slopes, Member Guest Pass, 25% off mid-week**

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Virginia Blue Ridge Mountains - Wintergreen Resort/Devils Knob, vacation rental in Wintergreen

Virginia Blue Ridge Mountains - Wintergreen Resort/Devils Knob

5 bedrooms
6 bathrooms
Sleeps 11
Match: Sleeps
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Marley's Cabin in Wintergreen, VA, vacation rental in Wintergreen

Marley's Cabin in Wintergreen, VA

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Heavenly view from the top of the Mountain.  Pet Friendly. Come relax!, vacation rental in Wintergreen

Heavenly view from the top of the Mountain. Pet Friendly. Come relax!

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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5 Star Luxury Home /Must Read Reviews, vacation rental in Wintergreen

5 Star Luxury Home /Must Read Reviews

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Cozy Condo in the Heart of Wintergreen!  Pet friendly., vacation rental in Wintergreen

Cozy Condo in the Heart of Wintergreen! Pet friendly.

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Spectacular post & beam contemporary home/ beautiful setting in center of resort, vacation rental in Wintergreen

Spectacular post & beam contemporary home/ beautiful setting in center of resort

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Newly Renovated 5-BR Home with Unbeatable Views at the Top of Wintergreen, vacation rental in Wintergreen

Newly Renovated 5-BR Home with Unbeatable Views at the Top of Wintergreen

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Best Location & View on Mtn - Pets OK - ski in/out, vacation rental in Wintergreen

Best Location & View on Mtn - Pets OK - ski in/out

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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SKI IN SKI OUT! Next to Mountain Inn, Sleeps 4 Best location on mountain!, vacation rental in Wintergreen

SKI IN SKI OUT! Next to Mountain Inn, Sleeps 4 Best location on mountain!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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2 Bdrm Condo - Mountain Views, Great for Skiing & Pet Friendly, vacation rental in Wintergreen

2 Bdrm Condo - Mountain Views, Great for Skiing & Pet Friendly

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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'SERENITY 4 ALL SEASONS', vacation rental in Wintergreen

'SERENITY 4 ALL SEASONS'

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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You deserve it all! Awesome Views, Comfy Condo, Elevator, & Shuttle Service!, vacation rental in Wintergreen

You deserve it all! Awesome Views, Comfy Condo, Elevator, & Shuttle Service!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful Wintergreen Retreat, vacation rental in Wintergreen

Beautiful Wintergreen Retreat

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Dog friendly! Spectacular Views!, vacation rental in Wintergreen

Dog friendly! Spectacular Views!

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Best views on Mountain!  BOOK NOW! Guest Passes!, vacation rental in Wintergreen

Best views on Mountain! BOOK NOW! Guest Passes!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spectacular Four Season View Mountain Retreat, vacation rental in Wintergreen

Spectacular Four Season View Mountain Retreat

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Mountain Home on the 1st Green of the Devils Knob Golf Course, vacation rental in Wintergreen

Beautiful Mountain Home on the 1st Green of the Devils Knob Golf Course

5 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps
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Three Timbers at Wintergreen Resort - Walk to Slopes - Guest Passes!, vacation rental in Wintergreen

Three Timbers at Wintergreen Resort - Walk to Slopes - Guest Passes!

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Highlands Condo, 3 Bedrooms, 3 Baths (Sleeps 8), vacation rental in Wintergreen

Highlands Condo, 3 Bedrooms, 3 Baths (Sleeps 8)

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Nestled Inn - New for Rent - Walk to Slopes! Townhome  2bed/2bath w/Loft, vacation rental in Wintergreen

The Nestled Inn - New for Rent - Walk to Slopes! Townhome 2bed/2bath w/Loft

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Breathtaking views! Beautifully decorated., vacation rental in Wintergreen

Breathtaking views! Beautifully decorated.

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Custom Builder just completely  remodeled this Mountain Chalet! ...with Hot Tub!, vacation rental in Wintergreen

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

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Mountain Escape at 'Wine-tergreen' Condo, vacation rental in Wintergreen

Mountain Escape at 'Wine-tergreen' Condo

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Authentic Log Cabin-  Available for Christmas due to last minute cancellation!, vacation rental in Wintergreen

Authentic Log Cabin- Available for Christmas due to last minute cancellation!

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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COMPLETELY RENOVATED with breathtaking VIEWS, vacation rental in Wintergreen

COMPLETELY RENOVATED with breathtaking VIEWS

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Safe, Secure, Super Clean Rural Retreat with Top of Mountain Views, vacation rental in Wintergreen

Safe, Secure, Super Clean Rural Retreat with Top of Mountain Views

4 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
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Ro's Retreat--Cozy Clean 3 Bed 3 full Bath condo Family Discounted, vacation rental in Wintergreen

Ro's Retreat--Cozy Clean 3 Bed 3 full Bath condo Family Discounted

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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New listing- Five minute walk to slopes and village!, vacation rental in Wintergreen

New listing- Five minute walk to slopes and village!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Mountain Getaway on 151 Brew Ridge Trail., vacation rental in Wintergreen

Mountain Getaway on 151 Brew Ridge Trail.

3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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UNOBSTRUCTED VIEWS OF BLUE RIDGE MOUNTAINS AND SKI SLOPES. BRAND NEW HOT TUB., vacation rental in Wintergreen

UNOBSTRUCTED VIEWS OF BLUE RIDGE MOUNTAINS AND SKI SLOPES. BRAND NEW HOT TUB.

4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Eagles Court Ski In/ Ski Out Condo, Free Wifi, Discounted Weekday Rates!!, vacation rental in Wintergreen

Eagles Court Ski In/ Ski Out Condo, Free Wifi, Discounted Weekday Rates!!

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Wintergreen house/ Skiing/ Appalachian Trail/ Golfing/Wineries and breweries, vacation rental in Wintergreen

Wintergreen house/ Skiing/ Appalachian Trail/ Golfing/Wineries and breweries

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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3 Bedroom Condo on the 18th hole within walking distance to many amenities., vacation rental in Wintergreen

3 Bedroom Condo on the 18th hole within walking distance to many amenities.

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Breathtaking views!! Overlooking the slopes, vacation rental in Wintergreen

Breathtaking views!! Overlooking the slopes

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Three Ridges Haven- Devils Backbone Brewing Company, vacation rental in Wintergreen

Three Ridges Haven- Devils Backbone Brewing Company

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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True Ski-in/out Condo! Step off the deck onto the beginner slopes!, vacation rental in Wintergreen

True Ski-in/out Condo! Step off the deck onto the beginner slopes!

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Ski in/ski out LUXURY slope side condo overlooking Wintergreen slopes. Beautiful, vacation rental in Wintergreen

Ski in/ski out LUXURY slope side condo overlooking Wintergreen slopes. Beautiful

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Wintergreen Resort -2 bdrm/2 bath condo. Amazing views!, vacation rental in Wintergreen

Wintergreen Resort -2 bdrm/2 bath condo. Amazing views!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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