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Roseland Holiday Homes

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    AU$305 Average
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    Don't let other travellers get your favourite Roseland area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 51 Rentals in Roseland
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    Beautiful Home and Best Value at Wintergreen1 / 7
    (3)Very good
    Roseland
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Roseland
    5 Bedrooms, 4 Bathrooms, Sleeps 22 Quick View
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    The following rentals are within 25 kilometres of Roseland.
    Chestnut Place Mountain Lodge1 / 24
    (2)Excellent
    Wintergreen
    5 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    TREELOFT- in the snow drift!1 / 14
    (5)Excellent
    Wintergreen
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Central Heating
    • Housekeeping Included
    • Patio
    • Balcony
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 March 2018
    Our family of six thoroughly enjoyed our weekend stay at this house. First of all, we’ve rented a lot of vacation homes, and I can’t think of a host who was more thoughtful or...
    Reviewed 6 February 2018
    This place seems bigger than 1100 sq ft, the best use of space. 3 Full bathrooms is a must when you have 8 people. Plenty of room to walk around and relax in front of fireplace...
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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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    Wintergreen, Virginia 22967
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Fit for a KING ( king size beds!)1 / 68
    (8)Excellent
    Wintergreen
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Children's Pool
    • Mountain Views
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Central Heating
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 November 2017
    This was our family's second trip to Fit for a King, and we are already planning our third next fall. This location is absolutely gorgeous in the fall, and with the close...
    Reviewed 25 October 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...
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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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    Wintergreen, Virginia 22958
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Simple Pleasures -N Ridge - Holidays Upon Us1 / 46
    (20)Excellent
    Wintergreen
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Mountain Views
    • Hot Tub
    • Skiing: Property Is In A Ski Resort
    • Cable/satellite TV
    • Sauna
    • Wi-Fi
    • Air Conditioning
    • Shared Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 January 2018
    Condo was well stocked and very comfortable for family of five. Loved the Christmas decorations and the fireplace. Could be cleaned a little better. Especially the oven that...
    Reviewed 28 February 2017
    What a lovely little place. We stayed with our family 2 sons and their wives and 2 of my grandchildren. Very accommodating. Although it was a bad weekend for tubing and...
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    About this property
    North Ridge Condos at Wintergreen Resort, VA - top of the mountain near Wintergarden and Devils Knob Golf/Tennis. WiFi available along with TV in each bedroom and den. Discount passes available for limited sporting activities. Walking distance to Wintergarden/ Devil's Knob Golf Course/Tennis Courts...
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    Wintergreen, Virginia 22958
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    CRAZY AMAZING get-a-way! (Crazy, in a GOOD way)1 / 41
    (9)Excellent
    Wintergreen
    5 Bedrooms, 6 Bathrooms, Sleeps 13 Quick View
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    Amenities & Details
    • Washer
    • Housekeeping Included
    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Shared Indoor Pool
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 February 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...
    Reviewed 9 January 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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    Location Information
    Wintergreen, Virginia 22958
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 13
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    Wintergreen -  Slope Side  w/ Resort Pass1 / 11
    (27)Excellent
    Wintergreen
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Sauna
    • Mountain Views
    • Cable/satellite TV
    • DVD Player
    • Shared Indoor Pool
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 February 2018
    So glad I spent 4 nights at this comfortable condo. I spent the first night enjoying pizza and a great fire in the wood fireplace. The owner left fire starter and there was...
    Reviewed 25 November 2017
    Great place. Beautiful view, comfortable and well maintained. This condo has everything you need. We enjoyed our stay immensely.
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    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...
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    Location Information
    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    WINTERGREEN MOUNTAIN HOUSE1 / 17
    (24)Excellent
    Wintergreen
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Hot Tub
    • Sauna
    • Mountain Views
    • Housekeeping Included
    • Internet Access
    • Central Heating
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 February 2018
    It was great place from start to finish! Very close to the slopes and great parking passes and other amenities. Mike was great at communicating with us about everything. 5...
    Reviewed 1 February 2018
    Had a great time at Wintergreen. Mike’s home is perfect for families and has everything that you could possibly need. The location is great and close to all the activities. Also...
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    About this property
    Time to start thinking about Skiing and tubing! Best snow conditions in years! Just Renovated, beautiful rental in the woods!!! New carpet/hardwood floors/tile bathrooms. New granite in kitchen, all new appliances, completely painted inside including ceilings! Close to ski slopes! Enjoy the...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Peaceful Seclusion in The Blue Ridge,Pet friendly1 / 28
    (10)Very good
    Lovingston
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Mountain Views
    • Porch
    • Washer
    • DVD Player
    • Patio
    • Parking
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 December 2016
    We booked this cabin to be used a base camp for several day hikes. It was perfect for my husband, myself and Crockett, our golden retriever. A quick trip to the Grocery...
    Reviewed 3 October 2016
    Beautiful two story cabin at the end of the road in the beautiful Virginia mountains. Very comfortable and has everything you can think of or need, including a record player...
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    About this property
    Davis Creek Cabin is a two story, two bedroom, 1 bath, cabin in the woods. Located at the base of the Blue Ridge Foothills, and sitting at the back of a cove in secluded, beautiful wooded land. Perfect for a romantic get-away, or family vacation! Our cabin is also family friendly, and pet...
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    Location Information
    Lovingston, Virginia 22949
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Season Mountain Inn Retreat1 / 23
    (6)Very good
    Wintergreen
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Mountain Views
    • Parking
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 February 2018
    We booked a ski weekend at Wintergreen at the end of February. While the weather didn't cooperate very much, we still decided to come for the weekend since we had the place...
    Reviewed 17 February 2018
    Condo was very nice and in a very convenient location. I would def reccomend staying here to anyone planning to visit the resort!
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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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    Location Information
    Wintergreen, Virginia 22958
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    A Cajun Chalet1 / 30
    (1)Excellent
    Wintergreen
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Shared Indoor Pool
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 March 2018
    What a great (long) weekend we had at the Cajun Chalet ! Dawn has everything you’ll need to cook at home after a day exploring the mountain.The secluded master bedroom upstairs...
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    About this property
    Welcome to A Cajun Chalet! We are located in the Blue Ridge Mountains, inside Wintergreen Resort. Beautiful modern home with 4 bedrooms, and 3 bathrooms, with a hot tub and a stream, and central AC and the All Access passes! The passes allow you to do the 3 things at Wintergreen that are Private....
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    On A Mountain Stream, Pet Friendly 3BR - Oakwood1 / 36
    (4)Very good
    Tyro
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Balcony
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Mountain Views
    • DVD Player
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful, pet-friendly vacation home is full of country charm, with country-style paintings on doors and walls scattered throughout. There's plenty of room to spread out, with a large living/dining room, a sun room, a covered deck overlooking the creek, and three bedrooms. The living room...
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    Location Information
    Tyro, Virginia 22952
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Escape to Campbell's Creek1 / 22
    (2)Excellent
    Tyro
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Mountain Views
    • Terrace
    • Parking
    • Outdoor Dining Area
    • Porch
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 April 2015
    This is just a charming place, in the middle of the Shenandoah Mountains...We came with our 7 year old grandson and enjoyed hiking, identifying trees and wildflowers, and most...
    Reviewed 7 November 2014
    Location is very nice and only a short distance from the main road. Short driving distance from numerous activities if you enjoy hiking or wineries or breweries. Just a great...
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    About this property
    Our cabin seems rustic, full of rough wood and handmade details that our father included when he built it in the 80s. But while seemingly rustic, it is warm, comfy, and charming. The downstairs has an ample living space with a living room (with working fireplace), dining room (seats 6...
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    Location Information
    Tyro, Virginia 22976
    Cabin Holiday Rental - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Secluded 2BR Pet-Friendly Cabin on Mountain Stream-Screen Porch1 / 20
    (1)Excellent
    Wintergreen
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • 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 Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Romantic, Pet-Friendly Cabin in Blue Ridge Mountains - Barnwood1 / 26
    (5)Excellent
    Tyro
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Mountain Views
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This romantic one-bedroom cabin in the Blue Ridge Mountains of Virginia is a delightful setting to bring that special person in your life. The peacefulness of the stream, just outside of the cabin, is a place to relax and let the worries of life fall away. The queen-size handmade pencil poster...
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    Location Information
    Tyro, Virginia 22952
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Cottage at Massies Mill & the Blue Ridge Mountains1 / 29
    (2)Excellent
    Massies Mill
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Mountain Views
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • DVD Player
    • Air Conditioning
    • Housekeeping Included
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 October 2017
    Very nice and comfortable place. Looking to return this winter when wintergreen mountain is open for skiing.
    Reviewed 31 August 2016
    It was just like staying in a cottage Southern Living would have featured...mountain views,privacy,cottage gardens, tranquil, & beautifully decorated. Many nearby attractions...
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    About this property
    Welcome to our cottage located in the foothills of the Priest Mountain. It's close to many hiking trails among the Blue Ridge Mountains, Crabtree Falls, local wineries and breweries. We are within a mile of the Tye River, which offers fishing, canoeing and kayaking. Wintergreen ski resort and...
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    Location Information
    Massies Mill, Virginia 22967
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3BR Wintergreen House w/Private Decks!1 / 22
    (2)Excellent
    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Wi-Fi
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 March 2018
    Our family enjoyed our stay and the house was great. Kitchen well equipped. Bedding really comfy. Allows pets and we enjoyed having our dog with us so family complete. Loved the...
    Reviewed 13 January 2018
    The house was clean, well equipped, and comfortable. I especially appreciate that they allow dogs. Our dogs are 12 and we like to travel with them when we can.
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    About this property
    For your next mountain getaway, why not stay somewhere that lets you truly take advantage of all the Blue Ridge Mountains have to offer? This premier Wintergreen vacation rental house does just that - ideally situated within walking distance of Wintergreen Resort, this home will let you enjoy easy...
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    Location Information
    Wintergreen, Virginia 22958
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    July 9 Week Available: Luxury Mountain House w/ Resort Membership1 / 13
    (7)Excellent
    Wintergreen
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Sauna
    • Cable/satellite TV
    • Shared Indoor Pool
    • Mountain Views
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 July 2017
    My wife and I are from Michigan and were looking for a central location to get together with our son, daughter-in-law, daughter, and 2 year old grandson who all live in...
    Reviewed 25 June 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...
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    About this property
    Week of July 9th still available. Aug 3-5 weekend available. New living room furniture - not shown in these pictures. We have the Wintergreen Resort membership so you have access to resort facilities that are closed to the public! 3500+sq ft Gorgeous/Custom Built House *** Two Master...
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    Location Information
    Wintergreen, Virginia 22957
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Wintergreen Resort 2 BR 2 BA Condo with LOW Rates1 / 12
    (15)Excellent
    Wintergreen
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Balcony
    • Porch
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 May 2017
    This is the perfect (feel like home) Wintergreen Condo. The furniture, beds and pillows were all comfortable. Nice VHS movie collection! The kitchen was stocked generously...
    Reviewed 15 March 2017
    Cozy and accommodated us very well. Nice to be able to use the fireplace and enjoyed the whirlpool tub. Will book again.
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    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...
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    Location Information
    Wintergreen, Virginia 22958
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    NEW! Wintergreen Home Mins from Area Attractions!1 / 39
    (1)Excellent
    Wintergreen
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    • DVD Player
    • Washer
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 May 2018
    This house is beautiful and perfect as a family getaway. It is quiet and peaceful. We never left the house or the mountain! Although you can do both very easily. The rooms...
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    About this property
    * 15% discount for 1 week bookings * Explore all the best of Wintergreen, Virginia from this newly built 5-bedroom, 4.5-bath vacation rental home that sleeps 12. Boasting a spacious deck with views, an outdoor grill and close proximity to a wide range of indoor and outdoor activities, this...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Down On 18th! Walk to Golf Clubhouse, Spa, Pool, Membership Access to Facilities1 / 16
    (1)Excellent
    Wintergreen
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Mountain Views
    • Shared Indoor Pool
    • Hot Tub
    • DVD Player
    • Wi-Fi
    • Sauna
    • Air Conditioning
    • Cable/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. 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 some space during your...
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    Location Information
    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Up-On 18th! Walk to Golf Clubhouse, Spa, Pool, Membership Access to Facilities1 / 15
    (2)Excellent
    Wintergreen
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Hot Tub
    • DVD Player
    • Mountain Views
    • Wi-Fi
    • Shared Indoor Pool
    • Sauna
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 January 2018
    It was an unbelievable location. The kitchen was great, beds were comfortable, and the view was beautiful.
    Reviewed 30 August 2017
    Our weekend at your condo in Wintergreen was superb! The layout, decor and practicality of the condo fit us to a tee! Thank you for allowing us to rent it for one night! We...
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    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. CHECK OUT OUR OTHER 2BR/2BA PROPERTY DIRECTLY BELOW THIS UNIT: PROPERTY ID 8742760 Do you have a large group/family. Do you need 4 Bedrooms? Do you need...
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    Location Information
    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Bear Dance Cabin at Wintergreen1 / 20
    (16)Excellent
    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Children's Pool
    • Parking
    • Washer
    • DVD Player
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 February 2018
    We had a great stay recently at Bear Dance Cabin at Wintergreen. The cabin has a wonderful fire place which is great after a day of skiing. The location is very convenient to...
    Reviewed 30 December 2017
    Thank you for sharing your beautiful cozy cabin with us! We had a delightful Christmas getaway! The cabin has everything we needed for our fun quality family time. Convenient...
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    About this property
    Our cabin is located near the very top, elev 3515ft, of Wintergreen mountain and is on the resort property; approximately 1.5 miles from the slopes. Wintergreen is an excellent place to vacation given the warmth of the people in this part of the eclectic Blue Ridge Mountains of Virginia and the...
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    Location Information
    Wintergreen, Virginia 22958
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pet Friendly Virginia Blue Ridge Mountain Cabin Rental-Foxwood1 / 19
    (4)Excellent
    Wintergreen
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Mountain Views
    • Air Conditioning
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Grill
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    • 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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    Location Information
    Wintergreen, Virginia 22952
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Cozy and Clean Resort Condo - New Ownership and listed for the first time!1 / 10
    (1)Excellent
    Wintergreen
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Skiing: Property Is In A Ski Resort
    • Housekeeping Included
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    • Mountain Views
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 May 2018
    We booked a short 3-day getaway over Spring break in April, and absolutely loved our time and stay in Ritta's condo. Not only is the condo conveniently located to everything...
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    About this property
    Take advantage of all the Blue Ridge Mountains have to offer while staying at this CHARMING FIRST FLOOR CONDO. This premier Wintergreen vacation rental is ideally situated within a short distance of Wintergreen Resort, on the 12th hole of Devils Knob Golf Course. From this home enjoy easy access to...
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    Location Information
    Wintergreen, Virginia 22967
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2BR Walkout Condo Private and Cozy!1 / 19
    (3)Very good
    Wintergreen
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Cable/satellite TV
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    • Mountain Views
    • Shared Outdoor Pool (Unheated)
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 March 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...
    Reviewed 10 March 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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    Mountaintop Resort-Center 3 Kings Twins PASSes1 / 37
    (7)Very good
    Wintergreen
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
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    • Hot Tub
    • Shared Indoor Pool
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 February 2018
    Great condo located on Wintergreen mountain convenient to everything. Three bedroom all with comfortable king size beds and each has its own full bathroom. Lots of pillows...
    Reviewed 10 December 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...
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    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...
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    Location Information
    Wintergreen, Virginia 22958
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Three Sisters Log Cabin1 / 11
    (10)Excellent
    Montebello
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
    • Balcony
    • Grill
    • Air Conditioning
    • Outdoor Dining Area
    • Hot Tub
    • Cable/satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 March 2017
    This is a unique experience in the blue ridge mountains. The cabin is like a museum. You will spend a lot of time outdoors, and be prepared for quiet homey evenings. Go with...
    Reviewed 21 February 2017
    Yes, the roads approaching the cabin might raise the hairs on the back of your neck, but this place is absolutely worth the visit. Three Sisters is the perfect spot for those...
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    About this property
    Virginia's Three Sisters Log Cabin is one of only a few surviving two story log cabin rentals along Virginia's scenic and world renowned Blue Ridge Parkway. A classic Virginia Appalachian log cabin, its peaceful feel and pure and simple character make it a most unusual rental property. It is a...
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    Location Information
    Montebello, Virginia 24464
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Montebello
    3 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    • Air Conditioning
    • Housekeeping Included
    • DVD Player
    • Waterfront
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Latitude N37.85541° & Longitude W79.19448°, Rock-n-Creek Cabin located just 1.5 miles off of The Blue Ridge Parkway at mile post 27 and perching atop Whetstone Ridge at 3,220 feet above sea level one of the highest ridges along the parkway system. We at Rock-n-Creek Cabin set ourselves...
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    Montebello, Virginia 24464
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 11
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    Nellysford
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Awesome views and only 5 minutes to Wintergreen Resort! We offer an immaculate 3 bedroom/2 bath home with everything you need to enjoy a mountain getaway vacation. The cottage is 1500 sq ft and has a gas fireplace, full kitchen and a large hot tub for relaxing after skiing or hiking! The views...
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    Location Information
    Nellysford, Virginia 22958
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tyro Slope-Side House Ski In/Out Yr Rnd Views w/AC1 / 16
    (3)Very good
    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • Grill
    • Balcony
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 January 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
    Reviewed 18 September 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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    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. The house...
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    Location Information
    Wintergreen, Virginia 22958
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Second Creek Farm near  Blue Ridge Parkway in Virg1 / 11
    (1)Excellent
    Montebello
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Classic Virginia white clapboard farmhouse - on land farmed by the same family since 1843, with views of Spy Rock and Sugar Hollow. This century farm is situated on what is considered one of the most beautiful landholdings in the area. Native trout streams abound on the property - the pond is...
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    Location Information
    Montebello, Virginia 24464
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Shared Indoor Pool
    • Wi-Fi
    • Mountain Views
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful, custom built and spacious three bedroom home located right on Devil’s Knob Golf Course at Wintergreen Resort, just a short distance to the ski slopes. This gorgeous post and beam designed home has three bedrooms: a king, queen, and a room with a full bed and a twin. There is a brand new...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Cabin at Wintergreen - VA Mt. Resort Luxury Rental1 / 24
    (24)Very good
    Wintergreen
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Hot Tub
    • Cable/satellite TV
    • Central Heating
    • Skiing: Property Is In A Ski Resort
    • Internet Access
    • DVD Player
    • Washer
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 February 2018
    My family and I headed to wintergreen for a ski vacation and found this gem of a vacation rental! It was well kept, clean, spacious, and overall great! Bonnie was easy to...
    Reviewed 15 January 2018
    We booked this cabin for a Thanksgiving reunion, as it was reasonably centrally located between points of origin in NC and DE. Pickings were slim by the time we decided to book...
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    About this property
    **** GUEST PASSES - WI-FI - FLAT SCREEN TV - HOT TUB - SCREENED IN PORCH - 2 MASTERS - RELAXATION - PEACE - & TRANQUILITY ALWAYS **** Bonnie Fagan has designed and built a fabulously luxurious 4-bedroom, 3-bath, log and stone vacation home in the Wintergreen VA Resort. The Fagan's offer this...
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    Location Information
    Wintergreen, Virginia 22958
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    The Mountain House1 / 9
    (1)Excellent
    Wintergreen
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Mountain Views
    • Wi-Fi
    • Washer
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    • Cable/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
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Gladstone
    5 Bedrooms, 3 Bathrooms, Sleeps 15 Quick View
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    • Washer
    • Patio
    • Housekeeping Included
    • DVD Player
    • Balcony
    • Grill
    • Central Heating
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Antebellum manor house with 5 bed rooms, privately situated on the James River and bordering a bold creek. Historically restored and original outbuildings. 66 acres to explore - there is a slave cemetery on the property as well as ruins of old cabins and an icehouse. It was originally a 1500 acre...
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    Location Information
    Gladstone, Virginia 24553
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 15
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    Mountaintop Lodge, Wintergreen Resort1 / 34
    (1)Excellent
    Wintergreen
    9 Bedrooms, 10 Bathrooms, Sleeps 24 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 May 2018
    We had a wonderful weekend celebrating my 50th birthday with 16 amazing individuals!! Beautiful home.
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    About this property
    One of Wintergreen’s premier mountain lodges (near the top of the mountain), this beautifully appointed 9 bedroom & 9.5 bath luxury property is ideal for corporate and executive conferences and retreats, family reunions and vacations, bachelor, bachelorette, and wedding party venues, couples...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 9 Bedrooms, 10 Bathrooms, Sleeps 24
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    Wintergreen
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We have a newly remodeled basement with its own door and private deck. We are .6 miles from the mountain inn/ski slopes. I have a pass for the chestnut / Rodes farm pools and tennis access . We are within a half hour of several winery's and brewery's. Wintergreen is a beautiful place to come and...
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    Location Information
    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Top of the Resort (Discounted Rates Available)1 / 24
    (9)Excellent
    Wintergreen
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
    • Grill
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 June 2018
    Our large family stayed at the Wintergreen Chalet for a 50th Wedding Anniversary weekend. The weekend we stayed was rainy and cloudy all weekend. The place was perfect for our...
    Reviewed 25 October 2017
    What a beautiful home! Our family of 12 was quite comfortable with plenty of room to spread out in this large and immaculate home. We could tell right away that the owner took...
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    About this property
    The Wintergreen Chalet is a sprawling 6-bedroom 4.5 bath home located at the top of Devil's Knob Mountain within the Wintergreen Resort in the Blue Ridge Mountains of Virginia. The home sleeps 12-14 comfortably and is available for rent daily or weekly throughout the year. Our home is set on a...
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    Location Information
    Wintergreen, Virginia 24477
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Sauna
    • Skiing: Property Is In A Ski Resort
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    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The ultimate Blue Ridge Mountain getaway awaits you at this 3-bedroom, 2-bath vacation rental house which sleeps 8 in Wintergreen. Located at the summit of Eagle's Swoop, this home has ski-in/out access to Wintergreen Resort's main ski slope, along with a private hot tub surrounded by towering...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Nellysford
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Parking
    • Cable/satellite TV
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    • Air Conditioning
    • Terrace
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to one of the most beautiful destinations in Nelson County Virginia. Situated on 200 beautiful acres. Overlooking Hamilton lake our log cabins are a unique blend of rustic and modern. The hand hewn logs give the warmth you would expect from a log home we've added modern amenities to make...
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    Nellysford, Virginia 22938
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Wintergreen
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick 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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    Location Information
    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    The Retreat at Wintergreen1 / 21
    (1)Excellent
    Wintergreen
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Central Heating
    • DVD Player
    • Mountain Views
    • Washer
    • Skiing: Property Is In A Ski Resort
    • Internet Access
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 May 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...
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    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...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    wintergreen pet ski hot tub fireplace hike golf pool pets firepl1 / 39
    (6)Average
    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
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    • Central Heating
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Home on one acre in wintergreen ski resort 5 - 10min walk to ski slopes, mountain inn restaurants ice rink basketball court ourdoor grill gift and ski equip shops rental and ticket office, market store deli beer wine pizza sundries, hiking , overlooks, newyears and july fourth fireworks Pets...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Wintergreen
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Skiing: Property Is In A Ski Resort
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on a wooded half acre lot on a quiet cul-de-sac, Split Rock Trail provides a feeling of privacy while offering easy access to everything the four-season Wintergreen Resort has to offer. Boasting a perfect layout for groups and families, Split Rock Trail has a fully furnished great room...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Wintergreen
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Sauna
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    • Skiing: Property Is In A Ski Resort
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled at the top of Wintergreen Mountain Resort within the Virginia wilderness, this 4-bedroom, 3-bath vacation rental house that sleeps 9 is the perfect destination for your next ski trip or relaxing getaway. With hiking trails, wineries, breweries, state parks, and world-class ski slopes within...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Lovingston
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • Parking
    • Air Conditioning
    • Private Garden
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We are located in the Village of Lovingston, VA. There are wineries, breweries, and distilleries. We have Wintergreen Ski Resort. The Lockn' Festival each August. Crabtree Falls and Humpback Rock for hiking. In Nelson Co., the Blue Ridge Parkway and Skyland Drive began. Nearby we have UVa's...
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    Location Information
    Lovingston, Virginia 22949
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Wintergreen
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    • Patio
    • Balcony
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    • Washer
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the best of Wintergreen Resort from this 2-bed, 2-bath Nellysford townhome, nestled in the Laurelwood complex! Featuring all of the comforts of home, this cozy abode takes up to 5 guests on a trip of a lifetime through the Blue Ridge Mountains - where skiing, hiking, swimming, golfing...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Wintergreen
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Mountain Views
    • Patio
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    • DVD Player
    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the best of Wintergreen from this 1-bath vacation rental studio located right in the Wintergreen Resort! Offering the best spot in the mountains, with splendid views of the ski lifts and 4th of July fireworks from the private balcony, this home offers the perfect spot for 2 guests...
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    Location Information
    Wintergreen, Virginia 22967
    Condo/Apartment - 1 Bathroom, Sleeps 2
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