Wintergreen Family & Kid Friendly Rentals
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0+ rooms, 2+ guests
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$1,000+
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170 rentals in Wintergreen.
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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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Wintergreen Resort -2 bdrm/2 bath condo. Amazing views!
2 bedrooms
2 bathrooms
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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VIEWS! Modern Mountain Retreat at Wintergreen
4 bedrooms
3 bathrooms
Sleeps 8
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Highlands Condo, 3 Bedrooms, 3 Baths (Sleeps 8)
3 bedrooms
3 bathrooms
Sleeps 8
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Mountain Getaway on 151 Brew Ridge Trail.
3 bedrooms
4 bathrooms
Sleeps 10
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»» 5 Min Walk to Slopes, Resort, & Restaurants ««
2 bedrooms
2 bathrooms
Sleeps 6
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Walk to slopes/Mountain Inn
4 bedrooms
4 bathrooms
Sleeps 10
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Large and Luxurious Exec 5BR House
5 bedrooms
5 bathrooms
Sleeps 12
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Wintergreen Five Star Rated One Bedroom Condo at affordable prices.
1 bedroom
1 bathroom
Sleeps 4
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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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Beautiful Mtn. View, Steps to Slopes, Member Guest Pass, 25% off mid-week**
2 bedrooms
2 bathrooms
Sleeps 8
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Wintergreen VA, 4 Season Resort Vacation Rental
5 bedrooms
4 bathrooms
Sleeps 14
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Now Booking for Hiking Tennis, Golf and Romantic Getaways
2 bedrooms
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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Heavenly view from the top of the Mountain. Pet Friendly. Come relax!
1 bedroom
2 bathrooms
Sleeps 4
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Virginia Blue Ridge Mountains - Wintergreen Resort/Devils Knob
5 bedrooms
6 bathrooms
Sleeps 11
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Ski-in/Ski-out condo with mountain views
2 bedrooms
2 bathrooms
Sleeps 9
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'SERENITY 4 ALL SEASONS'
5 bedrooms
3 bathrooms
Sleeps 12
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Marley's Cabin in Wintergreen, VA
4 bedrooms
4 bathrooms
Sleeps 8
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Perfect Place!! Fantastic Views, Skiing, Golf, Swim, Hiking, Wineries, etc.
3 bedrooms
3 bathrooms
Sleeps 6
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Family Time, Ski/tube, Hike, Swimming, Parking Pass, Great Restaurants & more!
4 bedrooms
4 bathrooms
Sleeps 8
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Spacious Home at the Top of the Resort (Discounted Rates Available)
6 bedrooms
5 bathrooms
Sleeps 14
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Gorgeous views, enjoy the fresh air, and wonderful hiking
4 bedrooms
5 bathrooms
Sleeps 8
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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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Spectacular Four Season View Mountain Retreat
3 bedrooms
3 bathrooms
Sleeps 10
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Perfect 3 BR w/ 2 Family Rms near Top of Mtn & Amenities
3 bedrooms
2 bathrooms
Sleeps 10
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Now Booking for Hiking Tennis, Golf and Romantic Getaways
2 bedrooms
2 bathrooms
Sleeps 4
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Dog-Friendly Vacation Home in Mountains: Skiing, Hiking, Near Breweries/Wineries
4 bedrooms
3 bathrooms
Sleeps 8
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250 TIMBERS. TOP OF MOUNTAIN. 1/1 SKI IN/SKI OUT CONDO. NO SMOKING.
1 bedroom
1 bathroom
Sleeps 4
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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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Best Location & View on Mtn - Pets OK - ski in/out
2 bedrooms
2 bathrooms
Sleeps 6
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Breathtaking views! Beautifully decorated.
3 bedrooms
3 bathrooms
Sleeps 6
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Beautiful Wintergreen Retreat
4 bedrooms
3 bathrooms
Sleeps 12
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Three Timbers at Wintergreen Resort - Walk to Slopes - Guest Passes!
5 bedrooms
4 bathrooms
Sleeps 12
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Beautiful Views, 5 Bed/Bath
5 bedrooms
5 bathrooms
Sleeps 12
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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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Authentic Log Cabin- Available for Christmas due to last minute cancellation!
4 bedrooms
2 bathrooms
Sleeps 10
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Ski-in/Ski-out: Beautiful Mountain & Valley Views - Walk to pool, fitness, trail
3 bedrooms
3 bathrooms
Sleeps 8
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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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Walk to Hiking Trails, Ski Slopes, Festivals, Restaurants, & Other Events
3 bedrooms
2 bathrooms
Sleeps 6
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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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Dobie - Ski-in Ski-out 1st floor inquire about all ski season/monthly rental
2 bedrooms
2 bathrooms
Sleeps 5
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Condo at Wintergreen! Join us for your winter vacation!
2 bedrooms
2 bathrooms
Sleeps 4
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1 BR condo w/ internet sleeps 4. Only 2 min walk to top of Mt.
1 bedroom
1 bathroom
Sleeps 4
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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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Beautiful 3BR/2BA on Prestigous Devils Knob Loop
3 bedrooms
2 bathrooms
Sleeps 8
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Great Views, Close To Ski/Golf/Hiking/family Fun
3 bedrooms
3 bathrooms
Sleeps 8
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Well-appointed 1BR condo, sleeps 4. Only 2 min walk to slopes & dining.
1 bedroom
1 bathroom
Sleeps 4
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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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