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Holiday Rentals with Pools in Waynesboro

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    20 Matching Rentals in the Waynesboro AreaView all 44 rentals
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    Pet Friendly 2BR Cabin in Blue Ridge Mtns of VA1 / 22
    (8)Excellent
    Waynesboro
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    The following rentals are within 25 kilometres of Waynesboro.
    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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    Simple Pleasures -N Ridge - Holidays Upon Us1 / 46
    (20)Excellent
    Wintergreen
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Chestnut Place Mountain Lodge1 / 24
    (2)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 7 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...
    Reviewed 6 January 2018
    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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    Wintergreen, Virginia 22958
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 15
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    A Cajun Chalet1 / 31
    (1)Excellent
    Wintergreen
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Shared Indoor Pool
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 March 2018
    What a great (long) weekend we had at the Cajun Chalet ! Dawn has everything you’ll need to cook at home after a day exploring the mountain.The secluded master bedroom upstairs...
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    About this property
    Welcome to A Cajun Chalet! We are located in the Blue Ridge Mountains, inside Wintergreen Resort. Beautiful modern home with 4 bedrooms, and 3 bathrooms, with a hot tub and a stream, and central AC and the All Access passes! The passes allow you to do the 3 things at Wintergreen that are Private....
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    Wintergreen, Virginia 22967
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Fit for a KING ( king size beds!)1 / 68
    (8)Excellent
    Wintergreen
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Children's Pool
    • Mountain Views
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Central Heating
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 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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    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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    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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    The Bear Dance Cabin at Wintergreen1 / 20
    (16)Excellent
    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Children's Pool
    • Parking
    • Washer
    • DVD Player
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 February 2018
    We had a great stay recently at Bear Dance Cabin at Wintergreen. The cabin has a wonderful fire place which is great after a day of skiing. The location is very convenient to...
    Reviewed 31 December 2017
    Thank you for sharing your beautiful cozy cabin with us! We had a delightful Christmas getaway! The cabin has everything we needed for our fun quality family time. Convenient...
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    About this property
    Our cabin is located near the very top, elev 3515ft, of Wintergreen mountain and is on the resort property; approximately 1.5 miles from the slopes. Wintergreen is an excellent place to vacation given the warmth of the people in this part of the eclectic Blue Ridge Mountains of Virginia and the...
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    Location Information
    Wintergreen, Virginia 22958
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pet Friendly Virginia Blue Ridge Mountain Cabin Rental-Foxwood1 / 19
    (4)Excellent
    Wintergreen
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    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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    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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    ALMOST HEAVEN AT WINTERGREEN RESORT!1 / 29
    (6)Excellent
    Wintergreen
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Beautiful and serene are words that come to mind. You must experience this wonderful piece of heaven. Wish I could have spent a month ... or more
    Reviewed 1 week ago
    If you want to get away from all the traffic and noise, this is the place to go. You can hike, play golf , have a spa day or just read a book. Or if you are like me and go with...
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    About this property
    GREAT new listing and just in time for FALL in Virginia! Beautiful remodeled home, with updated kitchen, open floor plan, lots of light, fantastic large deck with great porch furniture. Lovely location, close to everything. Walking distance to the ski bus route and to Tennis, and the...
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    Location Information
    Wintergreen, Virginia 22967
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2BR Walkout Condo Private and Cozy!1 / 19
    (3)Very good
    Wintergreen
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    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 29 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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    July 9 Week Available: Luxury Mountain House w/ Resort Membership1 / 13
    (7)Excellent
    Wintergreen
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Sauna
    • Cable/satellite TV
    • Shared Indoor Pool
    • Mountain Views
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 July 2017
    My wife and I are from Michigan and were looking for a central location to get together with our son, daughter-in-law, daughter, and 2 year old grandson who all live in...
    Reviewed 25 June 2014
    I recently rented this home for a bachelorette weekend for a friend who is more the outdoors type then the Vegas type. It was close to our home in Northern Virginia ~3 hours...
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    About this property
    Week of July 9th still available. Aug 3-5 weekend available. New living room furniture - not shown in these pictures. We have the Wintergreen Resort membership so you have access to resort facilities that are closed to the public! 3500+sq ft Gorgeous/Custom Built House *** Two Master...
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    Location Information
    Wintergreen, Virginia 22957
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Wintergreen -  Slope Side  w/ Resort Pass1 / 11
    (29)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 3 September 2018
    We stayed in Wintergreen for a few days in August. The resort is really quiet at that time. If you are avoiding crowds it’s a good place to go in the summer. The view from the...
    Reviewed 29 July 2018
    This unit had a great location and the views were excellent. Centrally located close to the Spa and restaurants as well. Plenty of parking. The unit itself was comfortable and...
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    About this property
    Welcome to Wintergreen! This condo is located near the top of the Highlands lift, within walking distance to the slopes and the nearby fitness and spa center. The included membership guest passes allow access to the fitness center, spa, golf, and tennis areas of the resort with a small fee. These...
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    Location Information
    Wintergreen, Virginia 22967
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    wintergreen pet ski hot tub fireplace hike golf pool pets firepl1 / 39
    (6)Average
    Wintergreen
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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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    Up-On 18th! Walk to Golf Clubhouse, Spa, Pool, Membership Access to Facilities1 / 15
    (4)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 21 August 2018
    The condo was very accommodating, but we went without hot water the whole weekend. The owner forgot to tell us that the hot water was off and needed to be turned on...
    Reviewed 18 January 2018
    It was an unbelievable location. The kitchen was great, beds were comfortable, and the view was beautiful.
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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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    Down On 18th! Walk to Golf Clubhouse, Spa, Pool, Membership Access to Facilities1 / 16
    (3)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 31 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 26 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
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    The Mountain House1 / 9
    (1)Excellent
    Wintergreen
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Mountain Views
    • Wi-Fi
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Central Heating
    • Secure Parking
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 5 bedroom, 2 1/2 bath home located in the Blue Ridge Mountains at Wintergreen Resort, Va.We are a four season community, with golf, tennis, swimming, boating, hiking (Appalachian Trail), skiing, ice skating, tubing, horseback riding, wine tasting, and more, located on our near our...
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    Location Information
    Wintergreen, Virginia 23831
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    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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    Amenities & Details
    • 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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