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Holiday Rentals near Wintergreen Resort

Wintergreen Resort, Route 664, Wintergreen, Virginia 22958
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    Travellers to Wintergreen are booking November dates now. Secure your holiday rental today, and have the perfect trip.
    All 341 Rentals in Wintergreen
    COMPLETELY RENOVATED with breathtaking VIEWS1 / 20
    (31)Excellent
    6.2 kilometres from Wintergreen Resort
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    5.0 kilometres from Wintergreen Resort
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    5.8 kilometres from Wintergreen Resort
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    A Cozy Mountain Home with Designer Decor1 / 15
    (8)Excellent
    5.1 kilometres from Wintergreen Resort
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Wintergreen, Virginia
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Comfy Mountain Retreat-Wintergreen Resort Lodge #21 / 16
    (18)Very good
    5.3 kilometres from Wintergreen Resort
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Wintergreen, Virginia
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
    Great Views, Close To Ski/Golf/Hiking/family Fun1 / 17
    (48)Excellent
    6.2 kilometres from Wintergreen Resort
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Wintergreen, Virginia
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    True Ski In/Out! Step off deck onto beginner slopes!1 / 21
    (37)Very good
    5.5 kilometres from Wintergreen Resort
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Wintergreen, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Hike, Ski, Visit Wineries & Breweries - 3BR (w/ the loft) /2BA, WiFi, Fireplace1 / 49
    (74)Very good
    5.4 kilometres from Wintergreen Resort
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Wintergreen, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Three Ridges Haven- Devils Backbone Brewing Company1 / 14
    (45)Very good
    0.6 kilometres from Wintergreen Resort
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Wintergreen, Virginia
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    Summertime Retreat1 / 33
    (59)Very good
    6.4 kilometres from Wintergreen Resort
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Wintergreen, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    'SERENITY 4 ALL SEASONS'1 / 20
    (63)Excellent
    6.2 kilometres from Wintergreen Resort
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Wintergreen, Virginia
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Best Location & View on Mtn - Pets OK - ski in/out1 / 43
    (148)Excellent
    5.6 kilometres from Wintergreen Resort
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Wintergreen, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Wintergreen Five Star Rated One Bedroom Condo at affordable prices.1 / 47
    (201)Excellent
    5.5 kilometres from Wintergreen Resort
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Wintergreen, Virginia
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Priced to rent!  Amazing views. Overlooking  Black Diamond Slope1 / 15
    (27)Very good
    5.6 kilometres from Wintergreen Resort
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Wintergreen, Virginia
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Ski Season is here! ! Book the Galileo House Now! Dogs Welcome!1 / 23
    (5)Very good
    6.7 kilometres from Wintergreen Resort
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Wintergreen, Virginia
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Family Time, Ski/tube, Hike, Swimming, Parking Pass, Great Restaurants & more!1 / 50
    (85)Excellent
    6.3 kilometres from Wintergreen Resort
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Wintergreen, Virginia
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Premium House with amazing VIEWS and upgraded amenities throughout1 / 24
    (120)Excellent
    4.7 kilometres from Wintergreen Resort
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Wintergreen, Virginia
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
    2 Bdrm Condo - Mountain Views, Great for Skiing & Pet Friendly1 / 24
    (73)Excellent
    2.2 kilometres from Wintergreen Resort
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Wintergreen, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    New listing- Five minute walk to slopes and village!1 / 26
    (55)Excellent
    5.1 kilometres from Wintergreen Resort
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Wintergreen, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    ️❤️ Gorgeous Wintergreen Condo – 2-min to Slopes1 / 23
    (29)Excellent
    5.5 kilometres from Wintergreen Resort
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Wintergreen, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Eagles Court Ski In/ Ski Out Condo, Free Wifi, Discounted Weekday Rates!!1 / 21
    (81)Excellent
    5.2 kilometres from Wintergreen Resort
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Wintergreen, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Mountain view with quick access to skiing, hiking, breweries, wineries, and more1 / 7
    (20)Excellent
    7.4 kilometres from Wintergreen Resort
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Wintergreen, Virginia
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Heavenly view from the top of the Mountain.  Pet Friendly. Come relax!1 / 50
    (190)Excellent
    6.4 kilometres from Wintergreen Resort
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Wintergreen, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Safe, Secure, Super Clean Rural Retreat with Top of Mountain Views1 / 26
    (47)Excellent
    6.4 kilometres from Wintergreen Resort
    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    Wintergreen, Virginia
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 9
    3 Bedroom Condo on the 18th hole within walking distance to many amenities.1 / 24
    (43)Excellent
    6.2 kilometres from Wintergreen Resort
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Wintergreen, Virginia
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    Enjoy winter on the mountain in our 4 bdrm/2 bath cabin!  Ski season is here!!!!1 / 23
    (23)Excellent
    7.4 kilometres from Wintergreen Resort
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Wintergreen, Virginia
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    House at Wintergreen! Book now for your Winter getaway!!1 / 29
    (18)Excellent
    5.1 kilometres from Wintergreen Resort
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Wintergreen, Virginia
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Spectacular Ski Chalet, 3 BR, 2.5 Bath, Great Location.1 / 23
    (96)Excellent
    7.1 kilometres from Wintergreen Resort
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Wintergreen, Virginia
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Devils Knob Loop Welcomes You1 / 20
    (14)Excellent
    5.9 kilometres from Wintergreen Resort
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Wintergreen, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Virginia Blue Ridge Mountains - Wintergreen Resort/Devils Knob1 / 23
    (63)Excellent
    6.2 kilometres from Wintergreen Resort
    5 Bedrooms, 6 Bathrooms, Sleeps 11 Quick View
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    Wintergreen, Virginia
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 11
    Beautiful Mtn. View, Steps to Slopes, Member Guest Pass, 25% off mid-week**1 / 33
    (102)Excellent
    4.9 kilometres from Wintergreen Resort
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Wintergreen, Virginia
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    2BR Ski-In Ski Out Condo!1 / 16
    (17)Excellent
    5.3 kilometres from Wintergreen Resort
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Wintergreen, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Ski-in/Ski-out: Beautiful Mountain & Valley Views - Walk to pool, fitness, trail1 / 25
    (74)Excellent
    6.1 kilometres from Wintergreen Resort
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Wintergreen, Virginia
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    *Having cabin fever at home?* Come stay at our cabin!1 / 28
    (9)Excellent
    5.1 kilometres from Wintergreen Resort
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Wintergreen, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Kick back at Virginia’s premier ski and golf resort1 / 29
    (99)Excellent
    6.8 kilometres from Wintergreen Resort
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Wintergreen, Virginia
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    BEAUTIFUL BLUE RIDGE MOUNTAINS1 / 38
    (78)Excellent
    6.7 kilometres from Wintergreen Resort
    5 Bedrooms, 7 Bathrooms, Sleeps 8 Quick View
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    Reviewed 18 September 2020
    Lovely and comfortable mountain home, perfect for groups and families. Beautiful views of the surrounding woods and the first green at Devil's Knob golf course. Great location...
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    Wintergreen, Virginia
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 8
    Pet friendly , Hot tub!! Private waterfall, prime resort location!1 / 38
    (88)Very good
    7.1 kilometres from Wintergreen Resort
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Wintergreen, Virginia
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
    Wintergreen Resort -2 bdrm/2 bath condo. Amazing views!1 / 17
    (59)Excellent
    7.2 kilometres from Wintergreen Resort
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Wintergreen, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Authentic Log Cabin-  Available for Christmas due to last minute cancellation!1 / 19
    (60)Very good
    7.5 kilometres from Wintergreen Resort
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Wintergreen, Virginia
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    You deserve it all! Awesome Views, Comfy Condo, Elevator, & Shuttle Service!1 / 22
    (129)Excellent
    6.5 kilometres from Wintergreen Resort
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Wintergreen, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    5 Star Luxury Home /Must Read Reviews1 / 16
    (83)Excellent
    7.5 kilometres from Wintergreen Resort
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Wintergreen, Virginia
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    Golf, Spa, Wine,or just a quiet getaway1 / 32
    (18)Very good
    6.4 kilometres from Wintergreen Resort
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Location Information
    Wintergreen, Virginia
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Walk to Market and activities. Exclusive pool for the Laurelwood community!1 / 12
    (32)Excellent
    5.1 kilometres from Wintergreen Resort
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Unheated)
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    Wintergreen, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Best views on Mountain! Just remodeled!  Breathtaking 5 Star! Book Now for Fall!1 / 49
    (125)Excellent
    2.1 kilometres from Wintergreen Resort
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Sauna
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    Location Information
    Wintergreen, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Marley's Cabin in Wintergreen, VA1 / 35
    (51)Excellent
    6.9 kilometres from Wintergreen Resort
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Wintergreen, Virginia
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Condo at Wintergreen! Join us for your winter vacation!1 / 29
    (85)Excellent
    7.1 kilometres from Wintergreen Resort
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Reviewed 25 September 2021
    I can’t say enough about this place. We ooh’d and ah’d for 5 minutes after walking in- even though we had seen the pics! Ladonna super great to work with. Condo, clean, lovely...
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    Wintergreen, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Walk to activities/trails/slopes1 / 17
    (40)Excellent
    5.5 kilometres from Wintergreen Resort
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Location Information
    Wintergreen, Virginia
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Golf Front Home1 / 14
    (57)Excellent
    7.0 kilometres from Wintergreen Resort
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Location Information
    Wintergreen, Virginia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    2 minutes from the shops and activities; Cozy 1 bedroom end unit, Dog Friendly!1 / 11
    (90)Very good
    5.5 kilometres from Wintergreen Resort
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Location Information
    Wintergreen, Virginia
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Breathtaking views!! Overlooking the slopes1 / 11
    (63)Excellent
    6.5 kilometres from Wintergreen Resort
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
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    Location Information
    Wintergreen, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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