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Massies Mill Holiday Rentals

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    Don't let other travellers get your favourite Massies Mill area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 53 Rentals in Massies Mill
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    Cottage at Massies Mill & the Blue Ridge Mountains1 / 29
    (3)Excellent
    Massies Mill
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Waterfront Retreat on the Piney River.  Relaxing Blue Ridge Mountain1 / 48
    (40)Excellent
    Massies Mill
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    The following rentals are within 15 kilometres of Massies Mill.
    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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    Peaceful Seclusion in The Blue Ridge,Pet friendly1 / 28
    (11)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 8 August 2019
    Absolutely loved our 2 night stay at Davis Creek cabin ,the place is unbelievable. There were 4 of us ,two couples from UK and I chose this cabin as it was near the Waltons...
    Reviewed 26 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...
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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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    Lovingston, Virginia 22949
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 6
    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 13 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 6 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
    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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    Tyro, Virginia 22952
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    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
    • 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
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
    Cozy, Clean and Convenient Resort Condo - Dog Friendly1 / 17
    (2)Excellent
    Wintergreen
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Skiing: Property Is In A Ski Resort
    • Housekeeping Included
    • Washer
    • Air Conditioning
    • DVD Player
    • Mountain Views
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 August 2019
    Nice rental! We had a great time. Condo was clean and within great distance of any activities we had planned.
    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
    Fit for a KING ( king size beds!)1 / 67
    (12)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 17 February 2019
    We usually go to the beach for our annual girls trip. 4 families now ages 15 to 40+ ;)! This time we wanted to do something different. The house was perfect with plenty of...
    Reviewed 13 November 2018
    Plenty of space for our group weekend getaway. The extra thoughtful touches, such as having the lights on for our arrival, and the fireplace set up for use were noticed 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
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Chestnut Place Mountain Lodge1 / 24
    (3)Excellent
    Wintergreen
    5 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Housekeeping Included
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • Cable/satellite TV
    • Children's Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2019
    Our extended family of six adults and five grandchildren (ages 1 to 8) fit nicely into this house, and we all had plenty of room and privacy. The Great Room is wonderful for...
    Reviewed 6 June 2018
    Dawn was a wonderful hostess. She was very helpful from the beginning. She text us several times on our way there to make sure we were going the safest route possible due to the...
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    About this property
    This is a SUPER beautiful modern home with 5 bedrooms, 3 full bathrooms and 2 half baths. All hardwood floors except for the tile kitchen.There are 2 big family rooms perfect for big families or groups of friends. 3 big flat screen TVs and pingpong. Two large dining room tables. Beautiful kitchen....
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    Location Information
    Wintergreen, Virginia 22958
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 15
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    CRAZY AMAZING get-a-way! (Crazy, in a GOOD way)1 / 46
    (10)Excellent
    Wintergreen
    5 Bedrooms, 6 Bathrooms, Sleeps 13 Quick View
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    Amenities & Details
    • Washer
    • Housekeeping Included
    • Mountain Views
    • Wi-Fi
    • Central Heating
    • Cable/satellite TV
    • Shared Indoor Pool
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 November 2018
    Dawn was one of a kind. She went further than any manager had to go. I was cooking a turkey & forgot the meat thermometer . She brought one up to me. How great is that. The...
    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...
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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
    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
    WINTERGREEN MOUNTAIN HOUSE1 / 17
    (26)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 6 January 2019
    Had a great time, the location is perfect just two minutes from the Mountain Inn. Very quiet, no one behind you but woods. Very well-stocked home, lots of games, linens...
    Reviewed 8 October 2018
    We rented this house for a relaxing weekend away. The house was very nice. We were not able to take advantage of the outside patio because the fog rolled in both days at 4:30 PM...
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    About this property
    Special for end of year Skiing! Contact me for special rates! 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...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Second Creek Farm near  Blue Ridge Parkway in Virg1 / 11
    (2)Excellent
    Montebello
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Mountain Views
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 October 2019
    The valley is beautiful! The farm is so peaceful! The views are spectacular! The people are so friendly!
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    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
    Wintergreen Home w/ Resort Passes, Steps to Slopes1 / 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. Boasting a spacious deck with views, an outdoor grill and access to a variety of members-only amenities, this home-away-from-home is sure to impress!...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Wintergreen
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Hot Tub
    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    • Grill
    • Central Heating
    • Washer
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully redone townhouse in the most PERFECT location at Wintergreen. We are directly across from the Wintergarden pools and fitness center and the amazing spa. Also located right on the bus route for easy access to everywhere. Its a lovely walk down the highlands trail to the main lodge. We...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    The Mountain House1 / 11
    (1)Excellent
    Wintergreen
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Central Heating
    • Shared Indoor Pool
    • DVD Player
    • Cable/satellite TV
    • Mountain Views
    • Wi-Fi
    • Washer
    • Secure Parking
    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 22967
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
    Book Spring/Summer: Luxury Mountain House on Golf Course 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 6 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
    Book now for Spring/Summer. June still available; most of July/Aug booked already. House is on mountain resort golf course and close to ski slopes. New living room furniture - not shown in these pictures. We have the Wintergreen Resort membership so you have access to resort facilities that...
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    Location Information
    Wintergreen, Virginia 22957
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    The Bear Dance Cabin at Wintergreen1 / 20
    (17)Excellent
    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Washer
    • DVD Player
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 November 2018
    Had a relaxing stay in comfy cabin with all the conveniences. Total privacy even though beautiful houses nearby. Clay was immediately available for questions; cabin was...
    Reviewed 7 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...
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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
    Tyro Slope-Side House Ski In/Out Yr Rnd Views w/AC1 / 16
    (4)Very good
    Wintergreen
    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
    Kid friendly
    Smoking allowed
    Reviewed 13 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 17 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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    Montebello
    3 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • 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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    Location Information
    Montebello, Virginia 24464
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 11
    Wintergreen Home w/Private Decks - Walk to Resort!1 / 20
    (2)Excellent
    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • 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 22 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 12 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
    Down On 18th! Walk to Golf Clubhouse, Spa, Pool, Membership Access to Facilities1 / 16
    (4)Very good
    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
    Reviewed 30 July 2018
    Condo was nice. Have no complaints. Good many stairs to the unit. Would have like to known . Good unit for the price.
    Reviewed 25 July 2018
    Easy access to trails, golf and tennis. Devils Knob first tee and just around the corner as well as the tennis facility offering clay courts and great instruction. Easy to...
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    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
    Up-On 18th! Walk to Golf Clubhouse, Spa, Pool, Membership Access to Facilities1 / 15
    (6)Very good
    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 22 August 2019
    Great condo right on the golf course and walking distance to the clubhouse and pool/spa. Member passes allowed us access to Wintergreen's wonderful amenities. Condo was clean...
    Reviewed 4 July 2019
    We enjoyed our visit to this condo and would definitely book it again. Jason was great to deal with. The condo is in a great location near activities and the view overlooking...
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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
    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Sauna
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    • 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 6 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 6
    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
    • 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
    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 9 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
    Beautiful Home and Best Value at Wintergreen1 / 7
    (3)Very good
    Roseland
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One of the nicest homes and BEST VALUES at Wintergreen! Snowmaking has already begun, suggesting a great ski season this winter. For new and repeat guests, we know that you will enjoy our newly renovated kitchen, just completed in December 2016. Rental of our 4-bedroom, 3.5-bath home includes...
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    Roseland, Virginia 22967
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    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 12 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
    Cabin at Wintergreen - VA Mt. Resort Luxury Rental1 / 24
    (25)Very good
    Wintergreen
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • 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 21 January 2019
    From the moment you reach the end of the cul-de-sac and rest your eyes on the ancient timbers of the home, you will feel your life's stress melt away. Well appointed with every...
    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...
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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
    Luxury Custom Home in Wintergreen Resort Area!1 / 45
    (1)Excellent
    Wintergreen
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Sauna
    • Air Conditioning
    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 January 2019
    This house had more than enough space for our group of 8 (2 families). Lots of room for everyone to spread out, and was a great location in relation to everything else in...
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    About this property
    Escape to the Wintergreen mountains in this custom 3-bedroom, 3.5 bathroom vacation rental home. Plush furnishings and modern amenities comfortably accommodate up to 10 guests throughout 3,500 square feet of well-appointed living space. This home is ideally situated on the Virginia mountainside in...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
    Wintergreen
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
    • Mountain Views
    • Washer
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    • Skiing: Property Is In A Ski Resort
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Discover the beauty of the Blue Ridge Mountains while retreating in this newly renovated Wintergreen vacation rental! Featuring 3 bedrooms, 3 bathrooms, and room for 7 guests, this home, complete with 2 decks, a fully equipped kitchen, and a wood-burning fireplace, is ideal for your next family or...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    Nellysford
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Patio
    • Waterfront
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    • Mountain Views
    • Cable/satellite TV
    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 our private 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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    Location Information
    Nellysford, Virginia 22938
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 4
    NEW! Wintergreen Home w/Deck & Community Amenities1 / 26
    (1)Very good
    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Sauna
    • Wi-Fi
    • DVD Player
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Loved the location and a beautiful cabin. We thoroughly enjoyed it and would certainly come again great location in the resort. Only a couple of things were not working but my...
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    About this property
    Located on a wooded half acre lot on a quiet cul-de-sac, this 3-bedroom, 2-bathroom vacation rental home provides a feeling of privacy while offering easy access to everything the four-season Wintergreen Resort has to offer. Your group of 10 will enjoy a furnished deck, game room, and 2,000 square...
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    Location Information
    Wintergreen, Virginia 22958
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Wintergreen
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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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
    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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    Wintergreen, Virginia 22967
    Holiday Rental House - 9 Bedrooms, 10 Bathrooms, Sleeps 24
    Wintergreen
    5 Bedrooms, 7 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful home overlooking the 1st green on Devils Knob Golf Course. There are 5 bedrooms, 5 full baths and 2 half baths. The home’s location is excellent: a short walk to the golf and tennis courts and club houses, Devils Grill Restaurant and the Wintergardenhas an indoor pool, spa and exercise...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 8
    Wintergreen
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Hot Tub
    • DVD Player
    • Mountain Views
    • Cable/satellite TV
    • Washer
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in the Wintergreen Resort community, with resort amenities, this 3-bed, 2.5-bath house features everything you need for a mountain retreat! Up to 8 guests can sleep comfortably in this vacation rental, making it perfect for family or friends. Enjoy everything from a fully equipped kitchen...
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    Location Information
    Wintergreen, Virginia 22958
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    NEW! Cozy Wintergreen Resort Condo w/ Pool Access!1 / 23
    (1)Excellent
    Wintergreen
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Skiing: Property Is In A Ski Resort
    • DVD Player
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 October 2018
    My husband and I stayed here with our 9 month old and dog. It was a great experience all the way from easy booking, great customer service, and affordable price to a beautiful...
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    About this property
    Pack your bags for an exciting Wintergreen Resort escape and stay at 'Monster Mountain Retreat!' Nestled amid the flourishing forests of the Blue Ridge Mountains, this 6-person property offers 2 bedrooms, 2 bathrooms, and access to a seasonal community pool. Whether you're skiing down the slopes...
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    Location Information
    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    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
    Wintergreen
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Parking
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Close your eyes and imagine opening the door to a beautifully handcrafted live edge oak breakfast bar with 4 leather bar stools, granite countertops and stainless steel appliances. As you walk into the living room, two plush, comfy leather sofas beckon you to rest & relax in front of the fireplace....
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Wintergreen
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Sauna
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    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Prepare for a relaxing getaway in Virginia's Blue Ridge Mountains at this magnificent vacation rental home. This spacious abode boasts in Nellysford 2,380 square feet of living space, 3 bedrooms, and 2.5 baths to host 8 people! Situated in the Wintergreen Resort, you'll be perfectly located for...
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    Location Information
    Wintergreen, Virginia 22958
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Wintergreen
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    • Patio
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    • 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
    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
    Wintergreen
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Mountain Views
    • Cable/satellite TV
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a great location with even better views as you stay at this 3-bedroom, 3-bathroom vacation rental condo in Wintergreen Resort! Boasting a 1,500-square-foot interior, accommodations for 8 guests, and breathtaking vistas from the balcony, this retreat can't be beaten. Spend snowy days skiing...
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    Location Information
    Wintergreen, Virginia 22967
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in the beautiful eastern slopes of the Blue Ridge Mountains awaits this charming cabin in Wintergreen Resort near Nellysford. With a rustic exterior but a trendy, fully furnished interior, you'll absolutely love returning to this cozy vacation rental home after skiing or hiking adventures....
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Wintergreen
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • DVD Player
    • Mountain Views
    • Wi-Fi
    • Cable/satellite TV
    • Skiing: Property Is In A Ski Resort
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Decorated by a professional artist and filled with the comforts of home, this Wintergreen Resort house promises a memorable stay! The 5-bedroom, 4-bathroom vacation rental features a furnished deck overlooking the golf course and access to a full array of amenities including a ski slope, spa,...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    Wintergreen
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Washer
    • DVD Player
    • Mountain Views
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pack your gear and head out to the mountains of Virginia for a stay at this amazing 5-bedroom 4-bath vacation rental, large enough to sleep the whole family and more! Wintergreen is a year-round resort offering activities for all ages. This home includes passes for 8 to take full advantage of the...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Wintergreen
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    • Mountain Views
    • Wi-Fi
    • Sauna
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Adventure and leisure combine at this luxurious 4-bedroom, 3-bathroom vacation rental home for 12 in Wintergreen. Located within minutes of top-notch golf courses, skiing at the Mountain Inn, and dozens of hiking trails, this 2,876-square-foot home has something for everyone. In addition to the...
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    Location Information
    Wintergreen, Virginia 22958
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Wintergreen
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the quintessential four-seasons getaway at this recently remodeled 4-bedroom, 3.5-bathroom Wintergreen Resort Condo situated minutes from skiing, tubing, hiking, biking, golfing, summer concerts, wine and beer festivals and so much more! With a polished 2,263-square-foot interior for 8...
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    Location Information
    Wintergreen, Virginia 22967
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Wintergreen
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Washer
    • Skiing: Property Is In A Ski Resort
    • Hot Tub
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Year-round, outdoor adventure awaits just around the corner from this 3-bed, 3.5-bath Roseland cabin! With a prime Wintergreen Resort location, the vacation rental provides quick access to ski slopes, 1.6 miles away, along with golf, hiking trails and mountain biking. For a little luxury, treat...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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