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House Rentals and Cabin Rentals in Wintergreen, VA

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    Travelers to Wintergreen are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 26
    5 of 5 bubbles (6) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 46
    5 of 5 bubbles (16) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    1 / 48
    5 of 5 bubbles (9) Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 13 | Quick View
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    1 / 27
    5 of 5 bubbles (7) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Children's Pool
    • Mountain Views
    • Wi-Fi
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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... View all property information
    Location Information
    Wintergreen, Virginia 22958
    5 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, not...
    5 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 Dawn...
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    1 / 17
    4.5 of 5 bubbles (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
    • DVD Player
    • Skiing: Property Is...
    • Hot Tub
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    • x
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    About this property
    Walk to Golf Clubhouse, Spa, Pool, Membership Access to all Facilities Sit on the Balcony and Enjoy the Gorgeous Golf /Fairway View. Membership Passes to golf, tennis and pool CHECK OUT OUR OTHER 2BR/2BA PROPERTY DIRECTLY ABOVE THIS UNIT: PROPERTY ID 2295258 Do you have a large group/family. Do... View all property information
    Location Information
    Wintergreen, Virginia 22967
    5 of 5 bubbles Reviewed November 30, 2016
    We rented this condo for our adult children over Thanksgiving. The condo was perfect! Though small, it lived much bigger - a very good layout with the bedrooms being away from...
    4 of 5 bubbles Reviewed September 21, 2016
    Overall this condo was very nice, except the mattresses and the bedding on the twin beds could be improved. The master bedroom was well done in all aspects, the kitchen was well...
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    1 / 9
    5 of 5 bubbles (4) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    • Satellite TV
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
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    • x
    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... View all property information
    Location Information
    Wintergreen, Virginia 22958
    5 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!
    5 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. The...
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    1 / 12
    5 of 5 bubbles (19) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
    • Air Conditioning
    • Sauna
    • Mountain Views
    • Satellite TV
    • DVD Player
    • Shared Indoor Pool
    • Skiing: Property Is...
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Welcome to Wintergreen! This condo is located near the top of the Highlands lift, within walking distance to the slopes and the nearby fitness and spa center. The included membership guest passes allow access to the fitness center, spa, golf, and tennis areas of the resort with a small fee. These... View all property information
    Location Information
    Wintergreen, Virginia 22967
    5 of 5 bubbles Reviewed December 14, 2016
    Had a great time at Wintergreen condo. Excellent accommodations, beds were comfortable, view was breath taking. Loved the Xbox, enjoyed the dancing game, and also watched a...
    5 of 5 bubbles Reviewed October 16, 2016
    This condo has great views of the mountains.Wintergreen Resort was 5 minutes from the Blue Ridge Parkway.Resturaunts in the resort were good food and convenient .
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    1 / 23
    5 of 5 bubbles (8) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Children's Pool
    • Satellite TV
    • Private Yard
    • Washer
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    We built our log cabin in 2005 just after we fell in love with the Wintergreen community. Much like you we searched for a place to stay at Wintergreen and after such a great experieince we decided to come back and look for a lot to build on. For us Wintergreen was perfect for a young family living... View all property information
    Location Information
    Wintergreen, Virginia 22958
    5 of 5 bubbles Reviewed 1 week ago
    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. We...
    5 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 process...
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    1 / 10
    4.5 of 5 bubbles (3) Very good
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • Grill
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    • Air Conditioning
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    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    You'll be delighted with this 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 on the Blue... View all property information
    Location Information
    Wintergreen, Virginia 22952
    1 / 13
    5 of 5 bubbles (5) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
    • Internet Access
    • Sauna
    • Satellite TV
    • Shared Indoor Pool
    • Mountain Views
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    March 17-19 weekend still available. All other Jan/Feb weekends sold out (along with first two weekends in March). We are near the slopes and have an exclusive parking pass for the two private ski lots. We have the Wintergreen Resort membership so you have access to resort facilities that are... View all property information
    Location Information
    Wintergreen, Virginia 22957
    5 of 5 bubbles Reviewed June 25, 2014
    I recently rented this home for a bachelorette weekend for a friend who is more the outdoors type then the Vegas type. It was close to our home in Northern Virginia ~3 hours away...
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    1 / 24
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Satellite TV
    • Mountain Views
    • Hot Tub
    • Internet Access
    • Sauna
    • Shared Outdoor Pool...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Have a truly special stay at this extraordinary 2-bedroom, 2-bathroom condo with room to comfortably accommodate 6 guests. Once you witness the serene sunset vistas overlooking the valley and mountain, you will never want to leave! Upon arrival, you’ll find that the adjacent free off-street... View all property information
    Location Information
    Wintergreen, Virginia 22958
    5 of 5 bubbles Reviewed September 14, 2016
    This condo is the perfect size for a couple or small family. It is really comfortable with warm, overstuffed couches, large TVs, a gaming system and internet. The accents are...
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    1 / 12
    5 of 5 bubbles (12) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Balcony
    • Porch
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Cozy and Convenient! Our Condo is centrally located for easy walking access to the full-service SPA, Golf course and indoor-outdoor Tennis facilities. We have been owners of this Condo for the past 9 years and love the Wintergreen Resort. We manage the Condo ourselves, to ensure the Condo is... View all property information
    Location Information
    Wintergreen, Virginia 22958
    5 of 5 bubbles Reviewed 4 days ago
    Mr. Mark allowed me to stay at his place for a weekend and it was perfect! I was just at the top of the Mountain, only a short shuttle ride away from the Wintergreen Resort. He...
    5 of 5 bubbles Reviewed 3 weeks ago
    We had a wonderful time at Wintergreen Mountain.And Mark's house it's very good. We enjoyed the accommodation. Thanks Mark.
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    1 / 23
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
    • Mountain Views
    • Shared Outdoor Pool...
    • Waterfront
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    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Wintergreen, Virginia 22952
    1 / 16
    4.5 of 5 bubbles (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Parking
    • Air Conditioning
    • Mountain Views
    • Grill
    • Balcony
    • Wi-Fi
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Wintergreen, Virginia 22958
    5 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
    5 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 instructions...
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    1 / 11
    4.5 of 5 bubbles (7) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Satellite TV
    • Balcony
    • Wi-Fi
    • Central Heating
    • Grill
    • Washer
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Wintergreen, Virginia 22958
    4 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.
    4 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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    1 / 37
    5 of 5 bubbles (6) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Mountain Views
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Skiing: Property Is...
    • Hot Tub
    • Shared Indoor Pool
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Come play on the mountain! The best location In the heart of Wintergreen Resort. Private but close to everything. 2 minutes to the slopes! You'll be right beside the pool, spa and the mountaintop golf course. All Resort PASSES cover all our guests for Aquatics and Fitness Center right next door... View all property information
    Location Information
    Wintergreen, Virginia 22958
    4 of 5 bubbles Reviewed December 10, 2015
    I stayed at this condo with my husband, daughter, and friends for a wedding. The location is great and near different attractions. The condo was clean and the owners had labels on...
    5 of 5 bubbles Reviewed June 24, 2014
    Our family of 6 plus a small child had a fun, relaxing week at this condo. The owner was very helpful and responsive during the planning period. We found the condo to be...
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    1 / 6
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
    • Satellite TV
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    • Skiing: Property Is...
    • Patio
    • Ocean Views
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Ski Slope Access across the street - Mountain Cabin/Chalet - Pet Friendly - Nature awaits you A beautiful Guest Cabin/Chalet/ or call it a peaceful home with windows all around so you can look out and see mountains, hills, forest, trees, wildlife and all that nature has to offer. She is a... View all property information
    Location Information
    Wintergreen, Virginia 22967
    1 / 9
    6 Bedrooms, 5 Bathrooms, Sleeps 16 | Quick View
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    • Porch
    • Grill
    • DVD Player
    • Satellite TV
    • Internet Access
    • Washer
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Newly built in 2004, this is a beautiful 6 bedroom, 4.5 bath home in the heart of Wintergreen Resort. Approximately 2.5 miles from the Mountain Inn, this home is convenient yet sits on a quiet street with little traffic. The yard is fenced (dogs are welcome), there are two master bedrooms on the... View all property information
    Location Information
    Wintergreen, Virginia 22967
    1 / 21
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Central Heating
    • DVD Player
    • Mountain Views
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    • Internet Access
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The Wintergreen Retreat Is a spacious house with an open floor plan, four large bedrooms and four full bathrooms. Two bedrooms have king beds, one has a queen bed and another has two twins and a bunk bed. We also have two Pack and Plays. The two king bedrooms have private bathrooms. The main level... View all property information
    Location Information
    Wintergreen, Virginia 22967
    5 of 5 bubbles Reviewed May 12, 2016
    Our stay at The Retreat at Wintergreen was a perfect mountain getaway! The home is very spacious, inviting and comfortable. The well stocked kitchen which is open to the family...
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    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    Location Information
    Wintergreen, Virginia 22967
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    1 / 22
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • ?
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    • x
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    Wintergreen, Virginia 22958
    1 / 5
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The Wintergreen Retreat is a vacation rental home within the Wintergreen Resort in Virginia, set among the beautiful Blue Ridge Mountains. This brand new charming mountain getaway is nestled on Wintergreen Mountain, just a few hundred yards from gorgeous scenic overlooks – and the perfect retreat... View all property information
    Location Information
    Wintergreen, Virginia 22958
    1 / 14
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Central Heating
    • Housekeeping...
    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Wintergreen, Virginia 22967
    5 of 5 bubbles Reviewed 1 week ago
    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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    1 / 21
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Washer
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    • Terrace
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    • Balcony
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
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    Wintergreen, Virginia 22967
    1 / 19
    4 of 5 bubbles (1) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Wi-Fi
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    • Mountain Views
    • Skiing: Property Is...
    • Washer
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    We invite you to stay in our newly renovated golf-front 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 access to the shuttle just outside the door. The Wintergarden Spa and the Nature Foundation are just... View all property information
    Location Information
    Wintergreen, Virginia 22967
    4 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 again...
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    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
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    Wintergreen, Virginia 22958
    1 / 19
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
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    • x
    About this property
    Luxury lower walk out home loaded with high end features including private access. Newly built Oasis in a secluded and tranquil area by Shamokin Springs Nature Preserve. Enjoy all of the comforts of your own home. All rooms feature ceiling fans and high end furnishings. Included also are TVs, iPod... View all property information
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    Wintergreen, Virginia 22967
    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
    • Terrace
    • DVD Player
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    • Balcony
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
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    Wintergreen, Virginia 22958
    1 / 19
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • ?
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    • x
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    Wintergreen, Virginia 22967
    1 / 21
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • DVD Player
    • Patio
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    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    The cottage has large front and rear decks, stairway to slopes, nice furniture and bedding, fully equipped kitchen, sleeps 6 with 1 king, 1 queen, and 2 twin beds..2 flat screen TVs, wireless internet and cable, DVD player, washer/dryer, living room has wood burning fireplace with wood provided,... View all property information
    Location Information
    Wintergreen, Virginia
    1 / 20
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
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    Wintergreen, Virginia 22958
    1 / 5
    5 of 5 bubbles (4) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • DVD Player
    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Revel in this condominium atop the Blue Ridge at award-winning Wintergreen Resort, 45 minutes southwest of Charlottesville, two hours and 45 minutes from Washington. The unit is available for weekly/weekend rentals at super discount rates from the owner. You'll have most amenities of the resort at... View all property information
    Location Information
    Wintergreen, Virginia 22958
    5 of 5 bubbles Reviewed December 27, 2016
    Our family stayed 4 nights over Christmas and we had a wonderful, comfortable stay. We liked having three beds and three baths. The kitchen functioned well and we cooked dinner...
    5 of 5 bubbles Reviewed December 8, 2014
    very nice accomidations. We had plenty to do around us and enjoyed our time there. Condo was nicely furnished.
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    1 / 24
    3 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Housekeeping...
    • Satellite TV
    • Internet Access
    • Hot Tub
    • Sauna
    • DVD Player
    • Central Heating
    • Shared Indoor Pool
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
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    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Wintergreen, Virginia 22958
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