Updated on Jul 20, 2026
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Type
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Private vacation home
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Bedrooms
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5
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Bathrooms
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3
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House Rules
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No pets allowed
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Children allowed: ages 0-17
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Smoking is not permitted
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No events allowed
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Max Occupancy
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18
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Host Language
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English
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Property Id
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288123
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Located just minutes from Old Rag Mountain, Whippoorwill Manor Farm is a destination that affords the rare experience to rent your own farm for a week or a weekend. The house was completely restored in 2005 adding a new addition that houses a large modern kitchen, and 3 full baths (over 3,800 sq. ft). One of Washington's top interior decorators designed the home specifically with the idea of family/friends use. Thus, the home has maintained its unique historical charm to include its wide hickory planked floors, log cabin rooms with stone fireplaces, and hand crafted wood work throughout the home. The original part of the house (log cabin) dates back to the 1700's and is the second oldest structure in Madison County. The farm even has a game building out back that's great to enjoy a drink while playing foosball or shuffleboard. There is also a professional outdoor ping pong table. The house has all the modern conveniences to stay connected including, direct TV and wireless internet (Please not that Broadband internet is not available in this area). Please note that this property is not set up to host weddings/events.
Great nearby outdoor activities such as: climbing Old Rag MT (the most spectacular hike in VA) or hiking White Oak Canyon to see its impressive upper and lower waterfalls, both parking lots are approximately 7 miles from the house both located in Shenandoah National Park. Whippoorwill Manor Farm is just minutes from Graves Mountain Lodge, Prince Michel, Sharp Rock, DuCard Vineyards and Shotwell Run Brewing.
Our objective is to treat our guests the same as we would our extended family/friends that come and visit the farm. Therefore, the important essentials are provided which includes: linens, towels, blankets, essential paper products, cleaning supplies, some laundry detergent, coffee, spices and condiments (no guaranteed stock), charcoal, lighter fluid and wood for fire place (some local cabins charge $40.00 just for the firewood). There is also a 25 pound a day ice maker. To assist in keeping the cleaning fee modest, you will need to make your own bed. Covers and blankets are on the beds with its sheets folded at the base. Finally, our Caretakers (Bill and Delores) live nearby and are available to personally address any concerns or questions you may have. Please be advised that the farm has the best available Internet in Madison County but it is not city speed and is not unlimited so we request you download videos prior to visit and not conduct gaming during stay.
The property is only 15-20 minutes from the historic towns of Culpepper, Madison and Sperryville, ideal for shopping and quality restaurants. Additionally, it serves as a perfect home vacation site to explore the many historic landmarks of the Shenandoah Valley and its vast natural beauty.
Come enjoy this truly unique and beautiful property for a peaceful and fun vacation or come with a group of friends for a long weekend to hike, bike, and enjoy each other with a number of local attractions and activities. On the property, there are a number of activities to enjoy such as corn hole, volleyball and horseshoes. In the evenings, the fire pit is a wonderful place to tell stories and share experiences year round. The house has a full back up generator in the event power is lost so your stay will not be disrupted if a major storm strikes.
For cycling enthusiasts from other parts of the country, the mountain scenery coupled with the quiet, safe, country roads are a national treasure to be experienced. The very popular Tour de Madison Bike Ride (held in mid-May every year), and the ride enjoys national stature. The Tour is not a race, but rather designed as a wonderful way to see the great scenic beauty of the Blue Ridge Mountains. They have routes for the entire family; you can choose between 16, 40, and 62 miles along country roads. If you can't make the actual weekend, the owner will provide you with the specific routes of the Tour so can enjoy them during your stay. Your group could even do a different 'century' every day for a week and beyond the initial few miles leaving/returning to the house; you will not have to cover the same ground twice!
Keywords: Historic farm home with log cabin section, private retreat on 110 secluded acres - ideal family reunion, hiking, active lifestyles
Located in Madison, this vacation home is in a rural area and in the mountains. Blue Quartz Winery and Sharp Rock Vineyards are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Shenandoah National Park and Thorton Gap Entrance Shenandoah. Kayaking and fishing offer great chances to get out on the surrounding water, or you can seek out an adventure with horse riding and cycling nearby.
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