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Waynesboro Holiday Homes

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    Don't let other travellers get your favourite Waynesboro area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 53 Rentals in Waynesboro
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    Pet Friendly 2BR Cabin in Blue Ridge Mtns of VA1 / 22
    (7)Excellent
    Waynesboro
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Shenandoah Valley Farmhouse1 / 32
    (1)Excellent
    Waynesboro
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Spacious house located in Shenandoah Valley1 / 8
    (4)Very good
    Waynesboro
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The following rentals are within 25 kilometres of Waynesboro.
    NEW! 1BR Lyndhurst Cabin on Farm w/Private Pond!1 / 25
    (1)Excellent
    Lyndhurst
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Waterfront
    • Patio
    • Internet Access
    • Parking
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Our family of 5 had a wonderful experience of restful family time. We enjoyed daily fires in the cabin and making s'mores at the fire pit by the pond. The cabin was very...
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    About this property
    Escape the hustle and bustle of your busy life and retreat to the woodlands of Virginia in the comfort of this 1-bedroom, 1-bathroom vacation rental cabin in Lyndhurst. Situated on a 15-acre working farm with a pond right outside the front door and a beautiful stocked stream running through the...
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    Lyndhurst, Virginia 22952
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Fit for a KING ( king size beds!)1 / 64
    (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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    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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    TREELOFT- in the snow drift!1 / 14
    (1)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 15 February 2017
    We love this are to stay on the wintergreen resort. You have quick access to blue and black slopes. Great trails in the area, quick drive or short walk to all main area for food...
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    About this property
    TREELOFT #1 is Located in a really GREAT spot, right in the Middle of Wintergreen Resort. It is walking distance to several overlooks, and the main lodge called the Mountain INN, and our Market. It is just 100 STEPS to the Tyro ski slope! 200 steps from there to the top of Eagles swoop and Big...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Pet Friendly 2BR House in Blue Ridge Mtns, Close to Blue Ridge Parkway1 / 30
    (7)Very good
    Lyndhurst
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Mountain Views
    • Parking
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 September 2015
    I stayed in Cabin Barnwood, the large one bedroom, by myself, traveling on an attempt at a personal retreat. The cabin was well-appointed. The bedroom had a well-made...
    Reviewed 29 April 2015
    The house we stayed in was not really a cabin in the woods but more like part of a neighborhood of mountain homes. The driveways are all paved. However, it was very clean and...
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    About this property
    Comfort is the word to describe this well-equipped mountain home, with all the amenities you need. Full kitchen, large decks, and wifi. Explore the Blue Ridge Parkway, the Skyline Drive, Shenandoah National Park, the Shenandoah Valley, and many more outdoor attractions. Looking for adventure?...
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    Location Information
    Lyndhurst, Virginia 22952
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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 2 weeks ago
    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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    Location Information
    Wintergreen, Virginia 22958
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    WINTERGREEN MOUNTAIN HOUSE1 / 17
    (22)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 1 week ago
    We traveled from Florida to bring our sons to see snow for the first time! The home was perfect for our little family! Our sons loved the bunk beds and the accommodations were...
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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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    Wintergreen -  Slope Side  w/ Resort Pass1 / 44
    (25)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 25 November 2017
    Great place. Beautiful view, comfortable and well maintained. This condo has everything you need. We enjoyed our stay immensely.
    Reviewed 31 October 2017
    Great view, exactly what we were looking for. Reasonably priced. Owner communicated quickly. Would return again.
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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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    Book Mar 2-4 Weekend: Luxury Mountain House near Ski Slopes w/ Resort Membership1 / 13
    (7)Excellent
    Wintergreen
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Hot Tub
    • Internet Access
    • Sauna
    • Cable/satellite TV
    • Shared Indoor Pool
    • Mountain Views
    • Air Conditioning
    • 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
    Dec, Jan & Feb weekends sold out. Book for Jan/Feb mid-week skiing. March weekends still available. We have brand new living room furniture - so new that the pictures are not yet posted online. We have the Wintergreen Resort membership so you have access to resort facilities that are closed to...
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    Location Information
    Wintergreen, Virginia 22957
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Mountain Chalet in Heart of Resort Sleeps 6-81 / 14
    (10)Very good
    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • Central Heating
    • Grill
    • Washer
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 May 2017
    We had an opportunity to stay here for 4 days and it was an exciting one. We thoroughly enjoyed each and every minute. My little girl enjoyed the stay and nearby play area. I...
    Reviewed 16 October 2014
    We stayed there with our friends. The location is perfect, just a walking distance to all attractions. The house was comfy with good size rooms.
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    About this property
    Nestled in the heart of Wintergreen, a year round resort, this cozy chalet home is a brief walk to the Mountain Inn, ski slopes, restaurants, shops, and market. The house is conveniently located on a private, wooded lot and offers a view of the mountain ranges during the winter months. On warm...
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    Location Information
    Wintergreen, Virginia 22958
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Brookview | Spacious Suite next to Old Trail Golf Course; Close to King Family1 / 17
    (1)Excellent
    Crozet
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Mountain Views
    • Balcony
    • DVD Player
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 October 2017
    Spacious and private, clean and comfortable. Great place to stay. Close to Blue Ridge Mountains and Charlottesville. Walking trails very close by.
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    About this property
    Brookview suite, in the foothills of the Blue Ridge Mountains, is a walkout basement location with a private entrance and private porch. It has a spacious living area, kitchenette, Queen bedroom, and shower bathroom. The neighborhood sidewalks lead you to walking/running trails, wildlife, a golf...
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    Location Information
    Crozet, Virginia 22932
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Pet Friendly Virginia Blue Ridge Mountain Cabin Rental-Foxwood1 / 19
    (3)Very good
    Wintergreen
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    Location Information
    Wintergreen, Virginia 22952
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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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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    Amenities & Details
    • Washer
    • Parking
    • Air Conditioning
    • Mountain Views
    • 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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    The Bear Dance Cabin at Wintergreen1 / 20
    (15)Excellent
    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Children's Pool
    • Cable/satellite TV
    • Private Garden
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    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...
    Reviewed 28 November 2017
    I can’t say enough about this place it was beautiful well-kept ideal location the owner was fabulous it was a beautiful holiday break with family looking forward to going again
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    About this property
    We decided to build our cabin after a family trip to WTG. We fell in love with the Wintergreen community and much like you we searched for a place to stay at Wintergreen. For us and our guests Wintergreen is a perfect getaway. Our cabin is located near the very top of the mountain and is on the...
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    Location Information
    Wintergreen, Virginia 22958
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Chestnut Place Mountain Lodge1 / 13
    (1)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 2 weeks ago
    We rented the house for a family and friends holiday get together and everyone had a great time. The house was well located, had excellent views, and was nice and quiet. 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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    4 Season Mountain Inn Retreat1 / 9
    (4)Excellent
    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 10 November 2016
    This was such a cute condo and was literally steps from the slopes. It overlooks the restaurant and ski school. Will definitely stay there again if it's avaiable!
    Reviewed 17 February 2016
    We skied Wintergreen 2 days. It was nice skiing, but also very cold (ie zero to 10 degrees). It was very convenient to have a place to stay and warm up so close to the skiing...
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    About this property
    Nestled in the Blue Ridge Mountains in the heart of Mountain Village, this loft condo has everything needed for a quick weekend getaway or an extended vacation. This unit is at the Mountain Inn, the heart of the Winter Village, and is the best condo for skiing at the resort. It is also ideal if...
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    Location Information
    Wintergreen, Virginia 22958
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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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 2 days ago
    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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    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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    Wintergreen
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Sauna
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Mountain Views
    • Hot Tub
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 BR, 2.5 Bath, 2 Family Rooms, All Access Member Passes, Minutes to Everything Whether you’re looking to get outside and play or just a little R&R, Wintergreen has everything you need and is set in the perfect location…the bright, colorful and peaceful Blue Ridge Mountains!! This split-level...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    • 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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    2BR Newly Renovated Private and Cozy!1 / 19
    (3)Very good
    Wintergreen
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • 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 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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    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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    Blueberry Hill Farm in Historic Shenandoah Valley1 / 22
    (11)Excellent
    Staunton
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Cable/satellite TV
    • Porch
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 November 2015
    This was our third stay at Blueberry Hill Farm. It is very comfortable and has a beautiful view. the hosts are very helpful.
    Reviewed 16 September 2015
    This was off the beaten path, quiet and relaxing. Restaurants are not very close; 2 to 30 minutes away but, we don't mind driving. The kitchen is well equipped and made it...
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    About this property
    A farm vacation suite in the beautiful Shenandoah Valley of Virginia midway between Staunton and Lexington. The suite is located in the upper part of our home with a private entrance via the second floor porch. Our exceptional feature is the year-round sun room where you have a tree-top view...
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    Staunton, Virginia 24476
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Air Conditioning
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    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Greenville
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Parking
    • Shared Garden
    • Shared Outdoor Pool (Unheated)
    • Mountain Views
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely & Cozy log cabin at charming country retreat at a working farm and equestrian center. Cabins are fully furnished and fully stocked with linens,towels, pots, pans, dishes and more. The facility has a full equestrian center, a lake for fishing and canoeing, lots of trails for walking or...
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    Location Information
    Greenville, Virginia 24440
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Pet-Friendly Secluded Mountain Cabin by Pool - Rockwood1 / 23
    (4)Very good
    Staunton
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Washer
    • Parking
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 August 2013
    Fabulous cabin, fully equipped with linens, etc. makes it especially great!!Loved the setting, the pool, ambience and no electronics. Great for familiesand anyone who enjoys...
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    About this property
    Very popular for families with teenagers, Cabin Rockwood is loved in the summer for its proximity to the swimming pool. As can be seen in the pictures, the pool is located only about 50 yards from the cabin. Inside you'll find a queen size bed in the master bedroom, as well as a full kitchen,...
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    Staunton, Virginia 22952
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    wintergreen ski hot tub hike golf pool pets firepl1 / 38
    (6)Average
    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Mountain Views
    • 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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    Fab mountaintop condo at Wintergreen Resort1 / 5
    (31)Very good
    Nellysford
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 September 2017
    When I entered my dates I didn't expect to find anything this beautiful. From the views to the hiking, it was a pleasant surprise. My Sister and I just wanted to find a quick...
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    About this property
    Three-bedroom, three-bath condo with mesmerizing eastern view and perfectly situated at classy Wintergreen Resort, Virginia's top skiing resort and a super escape from sweltering summer weather, with 45 holes of championship golf, clay tennis courts, and a nearby lake and beach for the kids....
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    Nellysford, Virginia 22958
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    Afton
    9 Bedrooms, 8 Bathrooms, Sleeps 24 Quick View
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    • Mountain Views
    • Parking
    • DVD Player
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    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're seeking the ideal destination for your upcoming celebration, family reunion or special event, look no further than 'Rockfish Valley Inn,' an incredible Afton vacation rental home, nestled on a large plot of land with stunning Blue Ridge Mountain views. This massive residence offers 9...
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    Location Information
    Afton, Virginia 22920
    Holiday Rental House - 9 Bedrooms, 8 Bathrooms, Sleeps 24
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    Greenville
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Hot Tub
    • DVD Player
    • Central Heating
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Penmerryl's Log Cabins are beautifully finished, fully equipped, Air Conditioned and heated. There are three bedrooms with the master having one Queen bed, and the other two having 2 twin beds in each room and there is a pullout sofa in the Living room. There are 1.5 baths. Equipped with ceiling...
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    Greenville, Virginia 24440
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Greenville
    16 Bedrooms, 14 Bathrooms, Sleeps 48 Quick View
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    • Central Heating
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Penmerryl Farm is located in the heart of the Shenandoah Valley, has beautiful mountain views and lots of activities on the farm. The farm is perfect for family reunions, wedding, corporate retreats and more! It is located on a working horse farm. It has 2 log cabins fully equipped with kitchens...
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    Location Information
    Greenville, Virginia 24440
    Private Room - 16 Bedrooms, 14 Bathrooms, Sleeps 48
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    Condo on the ridge with spectacular view1 / 6
    (6)Excellent
    Wintergreen
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • DVD Player
    • Mountain Views
    • Internet Access
    • Washer
    • Cable/satellite TV
    • Parking
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 October 2017
    We loved the view and the accommodations were good. Came for a weekend getaway and some relaxation with my partner. Wish we could have stayed longer. Would definitely...
    Reviewed 11 October 2017
    This condo was the perfect weekend getaway for me and my wife! It's near the top of the mountain at the Wintergreen Resort. This location provided us with beautiful views...
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    About this property
    Revel in this condominium atop the Blue Ridge at award-winning Wintergreen Resort, 45 minutes southwest of Charlottesville, two hours and 45 minutes from Washington. The unit is available for weekly/weekend rentals at super discount rates from the owner. You'll have most amenities of the resort at...
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    Location Information
    Wintergreen, Virginia 22958
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Crozet
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Mountain Views
    • Air Conditioning
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    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Mountain Retreat - 4 BR, Sleeps 10 Situated in Western Albemarle County, within 30 minutes of UVA and Charlottesville, and close to the historic town of Crozet, you will find this gorgeous 4 bedroom 4.5 bath private retreat situated on over 20 acres that enjoys, frontage along the Mooreman's...
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    Location Information
    Crozet, Virginia 22932
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Afton
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • DVD Player
    • Central Heating
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    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience glamping, Blue Ridge style. Our luxury yurt is located at the top of a small hill, in the center of a 70 acre farmstead surrounded by natural beauty. The property is located off a quiet country road yet still close to the Brew Ridge trail and 151, wineries, breweries, 20 minutes to...
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    Location Information
    Afton, Virginia 22920
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Spacious 6 Bedroom Home in the Wintergreen Resort1 / 24
    (8)Excellent
    Wintergreen
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
    • Parking
    • Grill
    • DVD Player
    • Air Conditioning
    • Hot Tub
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 22 June 2015
    This house is absolutely beautiful!! It had plenty of room for all of us, including the 8 kids. There were even games for them to play with. We had plenty of room in the kitchen...
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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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    Nellysford
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
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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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    Mountaintop Resort-Center 3 Kings Twins PASSes1 / 37
    (6)Excellent
    Wintergreen
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    • Shared Indoor Pool
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 25 June 2014
    Our family of 6 plus a small child had a fun, relaxing week at this condo. The owner was very helpful and responsive during the planning period. We found the condo to be...
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    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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    Cabin at Wintergreen - VA Mt. Resort Luxury Rental1 / 24
    (23)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 5 days ago
    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...
    Reviewed 13 August 2017
    Spent a week at this unique cabin. Had a great time! Owner was very responsive and helpful. The hot tub needed chemicals. That was corrected. The cover was very heavy and...
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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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    Maren Estate (Mountain Estate 20 min to UVA)1 / 24
    (1)Excellent
    Afton
    6 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
    • Hot Tub
    • Wi-Fi
    • Washer
    • Mountain Views
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 May 2017
    When I drove through the gate, I had to stop to take in the beautiful view of the house and surroundings. This was only matched by the views from the house of the valley and...
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    About this property
    Nestled in the foothills of the Blue Ridge Mountains just 20 minutes from Charlottesville, Maren Estate provides a friendly and relaxed setting for vacations, retreats, weddings, and all-around family fun. Located on a working farm, the estate is only minutes away from the Blue Ridge Parkway,...
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    Location Information
    Afton, Virginia 22920
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 14
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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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    • 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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    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Sauna
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Air Conditioning
    • Internet Access
    • 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/ski-out access to one of Wintergreen Resort's main ski slopes, along with a private hot tub surrounded by...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Wintergreen
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    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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    Wintergreen
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Washer
    • Mountain Views
    • Internet Access
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    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Sauna
    Suitability
    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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    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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    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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    Location Information
    Nellysford, Virginia 22938
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Crozet
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Quiet, Private and Very Comfortable! We thoroughly enjoyed our 2 night stay! Everything was clean, our bed was very comfortable and the owner was very helpful. We're so glad we chose it over a 'normal' hotel room. As is listed, there is no kitchen, but the coffee maker, small fridge, microwave and...
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    Location Information
    Crozet, Virginia 22932
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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