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Wintergreen Luxury Holiday Rentals

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136 rentals in Wintergreen.
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Views On The Shenandoah Valley And Minutes To The Slopes.
3 bedrooms
3 bathrooms
Sleeps 6
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Golf Front Home with Member Access to Devil's Knob and All Resort Amenities
3 bedrooms
2 bathrooms
Sleeps 10
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True Ski In/Out! Step off deck onto beginner slopes!
2 bedrooms
2 bathrooms
Sleeps 7
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Wintergreen Home w/ Deck - Near Skiing & Hiking!
3 bedrooms
2 bathrooms
Sleeps 8
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Condo at Wintergreen! Join us for your winter vacation!
2 bedrooms
2 bathrooms
Sleeps 4
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Ski-In Ski-Out Wintergreen Condo w/Balcony
1 bedroom
1 bathroom
Sleeps 4
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Large and Luxurious Exec 5BR House
5 bedrooms
5 bathrooms
Sleeps 12
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Walk to slopes/Mountain Inn
4 bedrooms
4 bathrooms
Sleeps 10
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Heavenly view from the top of the Mountain. Pet Friendly. Come relax!
2 bedrooms
2 bathrooms
Sleeps 4
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Wintergreen Five Star Rated One Bedroom Condo at affordable prices.
1 bedroom
1 bathroom
Sleeps 4
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Save time - get the best Wintergreen rentals sent straight to your email!
Family Time, Ski/tube, Hike, Swimming, Parking Pass, Great Restaurants & more!
4 bedrooms
4 bathrooms
Sleeps 8
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Beautiful Mtn. View, Steps to Slopes, Member Guest Pass, 25% off mid-week**
2 bedrooms
2 bathrooms
Sleeps 8
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Virginia Blue Ridge Mountains - Wintergreen Resort/Devils Knob
5 bedrooms
6 bathrooms
Sleeps 11
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Marley's Cabin in Wintergreen, VA
4 bedrooms
4 bathrooms
Sleeps 8
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Heavenly view from the top of the Mountain. Pet Friendly. Come relax!
1 bedroom
2 bathrooms
Sleeps 4
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5 Star Luxury Home /Must Read Reviews
4 bedrooms
4 bathrooms
Sleeps 12
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Spectacular post & beam contemporary home/ beautiful setting in center of resort
3 bedrooms
3 bathrooms
Sleeps 8
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Cozy Condo in the Heart of Wintergreen! Pet friendly.
1 bedroom
1 bathroom
Sleeps 4
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Newly Renovated 5-BR Home with Unbeatable Views at the Top of Wintergreen
5 bedrooms
4 bathrooms
Sleeps 12
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Best Location & View on Mtn - Pets OK - ski in/out
2 bedrooms
2 bathrooms
Sleeps 6
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SKI IN SKI OUT! Next to Mountain Inn, Sleeps 4 Best location on mountain!
1 bedroom
1 bathroom
Sleeps 4
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2 Bdrm Condo - Mountain Views, Great for Skiing & Pet Friendly
2 bedrooms
2 bathrooms
Sleeps 6
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'SERENITY 4 ALL SEASONS'
5 bedrooms
3 bathrooms
Sleeps 12
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You deserve it all! Awesome Views, Comfy Condo, Elevator, & Shuttle Service!
2 bedrooms
2 bathrooms
Sleeps 4
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Beautiful Wintergreen Retreat
4 bedrooms
3 bathrooms
Sleeps 12
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Dog friendly! Spectacular Views!
1 bedroom
2 bathrooms
Sleeps 4
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Best views on Mountain! BOOK NOW! Guest Passes!
2 bedrooms
2 bathrooms
Sleeps 6
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Spectacular Four Season View Mountain Retreat
3 bedrooms
3 bathrooms
Sleeps 10
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Beautiful Mountain Home on the 1st Green of the Devils Knob Golf Course
5 bedrooms
7 bathrooms
Sleeps 8
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Three Timbers at Wintergreen Resort - Walk to Slopes - Guest Passes!
5 bedrooms
4 bathrooms
Sleeps 12
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Breathtaking views! Beautifully decorated.
3 bedrooms
3 bathrooms
Sleeps 6
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Highlands Condo, 3 Bedrooms, 3 Baths (Sleeps 8)
3 bedrooms
3 bathrooms
Sleeps 8
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The Nestled Inn - New for Rent - Walk to Slopes! Townhome 2bed/2bath w/Loft
3 bedrooms
2 bathrooms
Sleeps 7
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Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!
3 bedrooms
2 bathrooms
Sleeps 8
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COMPLETELY RENOVATED with breathtaking VIEWS
3 bedrooms
3 bathrooms
Sleeps 8
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Safe, Secure, Super Clean Rural Retreat with Top of Mountain Views
4 bedrooms
5 bathrooms
Sleeps 9
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Ro's Retreat--Cozy Clean 3 Bed 3 full Bath condo Family Discounted
3 bedrooms
3 bathrooms
Sleeps 6
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Authentic Log Cabin- Available for Christmas due to last minute cancellation!
4 bedrooms
2 bathrooms
Sleeps 10
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New listing- Five minute walk to slopes and village!
2 bedrooms
2 bathrooms
Sleeps 6
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Mountain Getaway on 151 Brew Ridge Trail.
3 bedrooms
4 bathrooms
Sleeps 10
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UNOBSTRUCTED VIEWS OF BLUE RIDGE MOUNTAINS AND SKI SLOPES. BRAND NEW HOT TUB.
4 bedrooms
3 bathrooms
Sleeps 14
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Mountain Escape at 'Wine-tergreen' Condo
2 bedrooms
2 bathrooms
Sleeps 5
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Eagles Court Ski In/ Ski Out Condo, Free Wifi, Discounted Weekday Rates!!
2 bedrooms
2 bathrooms
Sleeps 7
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Wintergreen house/ Skiing/ Appalachian Trail/ Golfing/Wineries and breweries
5 bedrooms
4 bathrooms
Sleeps 14
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3 Bedroom Condo on the 18th hole within walking distance to many amenities.
3 bedrooms
2 bathrooms
Sleeps 9
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Breathtaking views!! Overlooking the slopes
2 bedrooms
2 bathrooms
Sleeps 4
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True Ski-in/out Condo! Step off the deck onto the beginner slopes!
2 bedrooms
2 bathrooms
Sleeps 8
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Ski in/ski out LUXURY slope side condo overlooking Wintergreen slopes. Beautiful
3 bedrooms
2 bathrooms
Sleeps 7
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Wintergreen Resort -2 bdrm/2 bath condo. Amazing views!
2 bedrooms
2 bathrooms
Sleeps 4
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