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Wintergreen Vacation Rentals

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    Travelers to Wintergreen are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    20 Reviews
    2 Bedrooms, Sleeps 4Quick View
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    18 Reviews
    3 Bedrooms, Sleeps 7Quick View
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    13 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    4 Reviews
    1 Bedroom, Sleeps 4Quick View
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    Amenities & Details
    • Satellite TV
    • Washer
    • Air Conditioning
    • Mountain Views
    • Parking
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed November 10, 2016
    This was such a cute condo and was literally steps from the slopes. It overlooks the restaurant and ski school. Will definitely stay there again if it's avaiable!
    Excellent of 5 bubbles
    Reviewed February 17, 2016
    We skied Wintergreen 2 days. It was nice skiing, but also very cold (ie zero to 10 degrees). It was very convenient to have a place to stay and warm up so close to the skiing...
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    About this property
    Nestled in the Blue Ridge Mountains in the heart of Mountain Village, this loft condo has everything needed for a quick weekend getaway or an extended vacation. This unit is at the Mountain Inn, the heart of the Winter Village, and is the best condo for skiing at the resort. It is also ideal if...
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    Wintergreen, Virginia 22958
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Reviews
    3 Bedrooms, Sleeps 8Quick View
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    • Washer
    • Parking
    • Air Conditioning
    • Mountain Views
    • Grill
    • Balcony
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed January 13, 2017
    Beautiful setting, lovely house with toasty fireplace! Could not have been better! When we come back to Wintergreen, this will be our first choice to stay1
    Excellent of 5 bubbles
    Reviewed September 17, 2015
    A group of eight friends stayed at this home in the Wintergreen Resort to enjoy a wine tasting weekend. Eric was extremely helpful in the booking process, and his...
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    About this property
    A skier's delight can be found at our Wintergreen vacation home on Squirrel Tree Lane, featuring ski in and ski out on the intermediate slope Tyro so that no time is wasted in traffic. Home is located 70' from the parking area, located in a private wooded area directly on the Tyro slope.<BR><BR>The...
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    Wintergreen, Virginia 22958
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    9 Reviews
    3 Bedrooms, Sleeps 6Quick View
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    • Children's Pool
    • Satellite TV
    • Private Yard
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed February 14, 2017
    Visited with my fiancé and 4 other friends for a ski weekend .... Love the place! No complaints what so ever! Easy access... owner communication was great... very comfortable...
    Excellent of 5 bubbles
    Reviewed November 3, 2016
    The cabin was a pleasantly rustic in design, but very clean and modern in construction. The location was convenient for exploring the surrounding mountains, and the rental...
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    About this property
    We decided to build our cabin after a family trip to WTG. We fell in love with the Wintergreen community and much like you we searched for a place to stay at Wintergreen. For us and our guests Wintergreen is a perfect getaway. Our cabin is located near the very top of the mountain and is on the...
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    Wintergreen, Virginia 22958
    Cabin - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    7 Reviews
    3 Bedrooms, Sleeps 8Quick View
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    • DVD Player
    • Satellite TV
    • Balcony
    • Wi-Fi
    • Central Heating
    • Grill
    • Washer
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Very good of 5 bubbles
    Reviewed October 15, 2014
    We stayed there with our friends. The location is perfect, just a walking distance to all attractions. The house was comfy with good size rooms.
    Very good of 5 bubbles
    Reviewed August 21, 2014
    Spent two nights at this chalet in July, 2014 with my wife, my daughter and her family. There were seven of us and the chalet easily provided the comforts needed for this size...
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    About this property
    Nestled in the heart of Wintergreen, a year round resort, this cozy chalet home is a brief walk to the Mountain Inn, ski slopes, restaurants, shops, and market. The house is conveniently located on a private, wooded lot and offers a view of the mountain ranges during the winter months. On warm...
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    Wintergreen, Virginia 22958
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 5Quick View
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    • DVD Player
    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    • Washer
    • Patio
    • Balcony
    • Hot Tub
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Terrace level apartment of personal mtn house w/ private entrance, shared hot tub on deck, 2 bdrms, full kth, stocked wine frig, Keurig w/ coffee, LR w/ vintage Pacmac game, private W/D. Deck w/ shared hot tub. Walk to lodge/restaurants & slopes. Seasonal mountain views. Wooded picnic area with...
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    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    3 Reviews
    3 Bedrooms, Sleeps 8Quick View
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    • Mountain Views
    • Air Conditioning
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Grill
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You'll be delighted with our Pet-Friendly, fully furnished mountain home, located just two miles from the Blue Ridge Parkway, and one mile from Sherando Lake. With all the comforts of home, you'll be able to enjoy the outdoors without roughing it! Spend the day hiking on mountains trails, driving...
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    Wintergreen, Virginia 22952
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    2 Reviews
    2 Bedrooms, Sleeps 5Quick View
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    • Wi-Fi
    • Satellite TV
    • Washer
    • DVD Player
    • Air Conditioning
    • Mountain Views
    • Shared Outdoor Pool (Unheated)
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed March 28, 2017
    The owner of this condo obviously cares a great deal about every detail and wanted to make sure our stay was an enjoyable one. The condo is immaculately clean, the beds are...
    Very good of 5 bubbles
    Reviewed March 9, 2016
    We loved staying here. Most everything we needed was supplied--even coffee and basic toiletries! The bedrooms were very nice. Full washer and dryer. We plan to stay here...
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    About this property
    We invite you to stay in our lovely totally updated golf-front walk-out condo, right in the heart of the Devils Knob area of Wintergreen Resort. Relax in the private, cozy cottage feel of our condo while having easy access to resort amenities. The Wintergarden Spa and the Nature Foundation are...
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    Location Information
    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    1 Review
    2 Bedrooms, Sleeps 4Quick View
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    • DVD Player
    • Mountain Views
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    • Washer
    • Patio
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Right on a mountain stream, this two-bedroom cabin is very private. No other cabins or homes can be seen. Two double beds make this very accommodating for four. The full kitchen with stove, refrigerator, microwave, coffeemaker, toaster, dishes, pots & pans, and silverware has everything you need...
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    Location Information
    Wintergreen, Virginia 22952
    Cabin - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, Sleeps 9Quick View
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    • Private Yard
    • Satellite TV
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to our mountain home at Wintergreen Resort! We fell in love with this house for the same reasons that we know you’ll love it. There’s plenty of sleeping space with 4 bedrooms, each with its own sliding glass door that opens onto a deck. There are three decks on the house, so plenty to...
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    Wintergreen, Virginia 22967
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Wintergreen, Virginia 22958
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    7 Reviews
    5 Bedrooms, Sleeps 10Quick View
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    Amenities & Details
    • Children's Pool
    • Mountain Views
    • Wi-Fi
    • Satellite TV
    • Washer
    • DVD Player
    • Central Heating
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed October 25, 2016
    My family (and extended family) stayed during the peak leafing weekend of the year. The house was incredible and suited our needs perfectly. The host was extremely helpful...
    Excellent of 5 bubbles
    Reviewed October 11, 2016
    We had 8 adults getting together for a long weekend of visiting many Wineries, Cidery's and Breweries just outside of Charlottesville. this is an ideal central location and...
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    About this property
    Now HERE is a really great house! Fit for a KING or two. This house has 4 large bedrooms with 2 of them having KING size beds. Then there is a Queen & 2 twins and then the loft has a twin day bed that has a pop up trundle so this could be another KING (that makes 3) ..or they can separate into...
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    Location Information
    Wintergreen, Virginia 22958
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    1 Review
    5 Bedrooms, Sleeps 10Quick View
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    • Mountain Views
    • Wi-Fi
    • Washer
    • DVD Player
    • Satellite TV
    • Central Heating
    • Secure Parking
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 5 bedroom, 2 1/2 bath home located in the Blue Ridge Mountains at Wintergreen Resort, Va.We are a four season community, with golf, tennis, swimming, boating, hiking (Appalachian Trail), skiing, ice skating, tubing, horseback riding, wine tasting, and more, located on our near our...
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    Location Information
    Wintergreen, Virginia 23831
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    1 Review
    3 Bedrooms, Sleeps 8Quick View
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    Amenities & Details
    • Central Heating
    • Housekeeping Included
    • Patio
    • Balcony
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed February 15, 2017
    We love this are to stay on the wintergreen resort. You have quick access to blue and black slopes. Great trails in the area, quick drive or short walk to all main area for food...
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    About this property
    TREELOFT #1 is Located in a really GREAT spot, right in the Middle of Wintergreen Resort. It is walking distance to several overlooks, and the main lodge called the Mountain INN, and our Market. It is just 100 STEPS to the Tyro ski slope! 200 steps from there to the top of Eagles swoop and Big...
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    Location Information
    Wintergreen, Virginia 22967
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    • Hot Tub
    • Internet Access
    • Washer
    • Shared Indoor Pool
    • Satellite TV
    • Sauna
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Wintergreen, Virginia 22958
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    • DVD Player
    • Parking
    • Central Heating
    • Patio
    • Washer
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Wintergreen, Virginia 22967
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Internet Access
    • Patio
    • DVD Player
    • Satellite TV
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Wintergreen, Virginia 22958
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Satellite TV
    • DVD Player
    • Internet Access
    • Balcony
    • Washer
    • Parking
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Wintergreen, Virginia 22967
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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    Amenities & Details
    • Patio
    • Washer
    • Internet Access
    • Satellite TV
    • Parking
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Location Information
    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Amenities & Details
    • Sauna
    • Air Conditioning
    • Shared Indoor Pool
    • Satellite TV
    • DVD Player
    • Grill
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Wintergreen, Virginia 22958
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Mountain Views
    • Shared Indoor Pool
    • Hot Tub
    • DVD Player
    • Wi-Fi
    • Sauna
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax, Golf, Beautiful Views, Passes for Golf, Tennis and Pool Please be advised we request a two night stay on the weekends, during the winter season. CHECK OUT OUR OTHER 2BR/2BA PROPERTY DIRECTLY ABOVE THIS UNIT: 8743003 Do you have a large group/family. Do you need 4 Bedrooms? Do you need...
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    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 8Quick View
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    Amenities & Details
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • Washer
    • Internet Access
    • Patio
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Wintergreen, Virginia 22958
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    • Hot Tub
    • DVD Player
    • Mountain Views
    • Wi-Fi
    • Shared Indoor Pool
    • Sauna
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gorgeous Views/Beautiful Weather/Perfect Sectional Couch to relax!Golf/Pool Pass Please be advised we request a two night stay on the weekends, during the winter season. CHECK OUT OUR OTHER 2BR/2BA PROPERTY DIRECTLY BELOW THIS UNIT: PROPERTY ID 8742760 Do you have a large group/family. Do you...
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    Location Information
    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Parking
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Air Conditioning
    • Patio
    • DVD Player
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Wintergreen, Virginia 22958
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, Sleeps 6Quick View
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    Wintergreen, Virginia 22958
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 6Quick View
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    Location Information
    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Parking
    • Internet Access
    • Satellite TV
    • Patio
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Wintergreen, Virginia 22967
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    9 Reviews
    5 Bedrooms, Sleeps 13Quick View
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    • Washer
    • Housekeeping Included
    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Shared Indoor Pool
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed February 2, 2017
    We had a large group of ski patrol women and this house was perfect! Dawn was great at communication and was always available via text. The location was great. The large...
    Excellent of 5 bubbles
    Reviewed January 9, 2017
    Booked the house for the New Year's weekend for family skiing, hiking and celebration. Mission accomplished! House was great with plenty of room. The house was well appointed...
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    About this property
    This is a really amazing home! It is so perfect for all kinds of groups because it has 3 SERIOUS master suites. You could say it is perfect for "separate togetherness". The main floor has the kitchen that overlooks a huge deck right on the 16th tee box of Devils Knob Golf course, a big dinning...
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    Wintergreen, Virginia 22958
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 13
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    • Washer
    • Air Conditioning
    • Sauna
    • Shared Indoor Pool
    • DVD Player
    • Hot Tub
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Internet Access
    • DVD Player
    • Grill
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    Pet friendly
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    Smoking allowed
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    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, Sleeps 4Quick View
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    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Wintergreen, Virginia 22967
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • DVD Player
    • Satellite TV
    • Internet Access
    • Shared Indoor Pool
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    • Housekeeping Included
    • Central Heating
    • Sauna
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Wintergreen, Virginia 22958
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Parking
    • Satellite TV
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    Wintergreen, Virginia 22958
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    • Air Conditioning
    • DVD Player
    • Satellite TV
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    • Patio
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    Wintergreen, Virginia 22958
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, Sleeps 8Quick View
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    • Grill
    • Terrace
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Balcony
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Wintergreen, Virginia 22958
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    • DVD Player
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Internet Access
    • Grill
    • Satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Wintergreen, Virginia 22958
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 10Quick View
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    Wintergreen, Virginia 22967
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, Sleeps 6Quick View
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    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Wintergreen, Virginia 22967
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Wintergreen, Virginia 22967
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Location Information
    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Wintergreen, Virginia 22958
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, Sleeps 8Quick View
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    • Central Heating
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    Wintergreen, Virginia 22967
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Location Information
    Wintergreen, Virginia 22958
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Location Information
    Wintergreen, Virginia 22957
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    • Washer
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    • Terrace
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    Location Information
    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bathrooms, Sleeps 7
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