Stunning Family/Friends Retreat,110 Private Acres, Renovated Historic Home

Madison, Virginia
$699 avg/night
Bed 5

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 18

Max Sleeps

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 widehickory 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

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    5 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 3600 Sq Ft (334 Sq M)
  • KITCHEN

    Blender Cleaning Supplies Coffee Grinder Dishwasher Microwave Oven Refrigerator Spices Stovetop
  • LAUNDRY

    Laundry Detergent Laundry Facilities Washing Machine And Dryer
  • PARKING

    Car Required Onsite Parking
  • INTERNET

    WiFi Available
  • OUTDOORS

    Balcony Barbecue Grill Firepit Free Firewood Garden Outdoor Furniture
  • POOL/SPA

    Sauna
  • BATHROOMS

    3 Bathrooms Hair Dryer Shampoo Shower Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Bicycle On Site Cycling Nearby Fitness Center Hiking Nearby Hiking/biking Trails Nearby Horse Riding Nearby Hunting Nearby Kayaking Nearby Rock Climbing Nearby Wildlife And Game Walks Nearby Winery Tours Nearby
  • ENTERTAINMENT

    Arcade/game Room DVD Player Foosball Table Stereo Table Tennis TV With Cable/satellite Service
  • LIVING SPACES

    Fireplace Living Room Wood Stove
  • CLIMATE CONTROL

    Air Conditioning Heating
  • LOCATION HIGHLIGHTS

    In A Rural Location In The Mountains
  • SERVICES AND CONVENIENCES

    Iron/ironing Board Phone
  • SUITABILITY/ACCESSIBILITY

    If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. Smoke-free Property Wheelchair Accessible

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 18

Map Map

School District Rates & Availability

Review Review

  • jeanne p.

    Submitted Dec 16, 2025

    Stayed Nov 21, 2025

    Excellent

  • Rachel H.

    Submitted Nov 13, 2025

    Stayed Nov 7, 2025

    This is our fifth time at Eric’s lovely property and we had a wonderful time, as always. The house has ideal accommodations for many adults and the kitchen is fully stocked with any tool you could need. Eric is always very responsive and welcoming. The property is beautiful. I highly recommend staying here!

  • Chris F.

    Submitted Sep 22, 2025

    Stayed Sep 19, 2025

    We loved this place. We were there for a family event in the area, so sadly we didn't get to enjoy it as we would have liked to. I'd love to go back and spend more time there. It was so well stocked and family friendly. Communication was great. Beds were comfy. Beautiful place with lots to do.

  • Gregory D.

    Submitted May 16, 2025

    Stayed May 1, 2025

    This property is the best short term rental I’ve encountered. The house is stocked with everything you need and the amenities like the sauna, game room, and BBQ pits are all welcome features to the immaculate grounds. We made many fond memories and look forward to returning.

  • michael d.

    Submitted Feb 18, 2025

    Stayed Feb 14, 2025

    Everything was perfect. Everything you could possibly need was there. Great experience would definately return

  • Rachel H.

    Submitted Feb 10, 2025

    Stayed Feb 7, 2025

    We love Whipporwill Manor! The house has everything you can think of - seriously, everything! Our group took advantage of the bikes, the fully equipped kitchen, the ample space for lounging and playing chamber music, and the perfectly suited bedrooms for our configuration. The property is gorgeous and the home is cozy. I can’t recommend this listing enough!

  • Matt S.

    Submitted Jan 6, 2025

    Stayed Dec 28, 2024

    This was our family's second visit to Whippoorwill and it was even better than our first. The house and property are so unique and peaceful. The owner has been fantastic and goes above and beyond to make the property feel like a home; not just a rental. Everyone in our family off 11, ranging in ages from 9 to 78, absolutely love this special place!!

  • Wendy K.

    Submitted Nov 24, 2024

    Stayed Nov 16, 2024

    Second time here and def a fave with all our family! Spending a week with our kids and grandkids is so special, and this place fits us all. Love the property where the kids can be outside on their own while parents relax over a cup of coffee. Enjoyed the warm November weather during the days, and fires at night, both inside and out. Can’t wait til next time!

  • Rachel H.

    Submitted Nov 22, 2024

    Stayed Nov 8, 2024

    This is our third time having a group of friends cook and play chamber music at Eric’s wonderful home. It’s the perfect size, with excellent sleeping arrangements, a fantastic kitchen, and plenty of other things to keep us occupied, particularly the trails. We already have our next stay booked!

  • James C.

    Submitted Oct 14, 2024

    Stayed Sep 26, 2024

    We love this place ! I think it’s our 12th year !

  • Emily B.

    Submitted Oct 5, 2024

    Stayed Sep 13, 2024

    This was my 7th stay at Whippoorwill over the past 10 years and it never disappoints. It is such a special and wonderful spot. Perfect for group gatherings. You will not find a better stocked kitchen - from a Kitchen Aid mixer to every utensil you could ever want. I panicked when I realized I had forgotten baking soda and powder, opened a cabinet door and there it was. The owners are constantly adding to the property. My toddlers were delighted to find an adorable playhouse with a working doorbell and a sandbox. Highlight of their trip! I loved being able to watch them play from the kitchen window. The storage room is stocked with the best supplies for the grill and anything you could need outdoors. The ice machine is so amazing for a large group, no more ice runs to a gas station. The internet worked great much to the delight of the teenagers. We had a birthday dinner for my mom under the pergola and stars. This is a place where memories are made. Can’t wait for our next stay!

  • Holly J.

    Submitted Aug 18, 2024

    Stayed Aug 9, 2024

    This is our 4th stay at Eric's place and I think that speaks for itself. This property is well taken care of and is such an amazing space. The house is beautiful but my favorite thing about this place is all the outdoor space, the fire pit, the hiking trails etc we will be back! Thanks for an awesome bday trip!

  • John P.

    Submitted Aug 13, 2024

    Stayed Jul 25, 2024

    I left a long review earlier.

  • Denice O.

    Submitted Aug 7, 2024

    Stayed Jul 31, 2024

    We absolutely loved the place!! The hosts did not forget anything and provided all the essentials. They prepared us very well on what to bring. We loved reading the book about the family and home. We were there for my daughters wedding and wished we had more time to just hang out on the property and explore the many trails around it. It truly was a beautiful place!! Our whole family said that we would love to come back(maybe when it isn't as hot). Thank you for providing a wonderful place to enjoy the beautiful surroundings.

  • Toniann B.

    Submitted Jul 5, 2024

    Stayed Jun 28, 2024

    This is our second time back to Whippoorwill Manor Farm for our annual family vacation. This house and property quite literally have everything to keep kids and adults entertained. Bikes, game room, sauna, sports/activities galore, trails, wildlife (bears too!), fire pit, outdoor seating, and acres upon acres to let the kids play like kids should. There is just so much room inside and out- great for large gatherings. The house is so well appointed with anything you might need…especially the kitchen. The entire process from booking to departing was smooth. We’ve been holding our annual family vacation with a house rental for 14 years now, and this is by far everyone’s favorite property. If you are looking to unwind and have some fun with friends and family- this is the place. Private, quiet piece of property…but not too far from groceries, hiking, tubing, wineries, and many other activities!

  • Daniel S.

    Submitted Jun 5, 2024

    Stayed May 27, 2024

    We've been staying at WMF for years, and it always blows us away how pristine, comfortable and peaceful it is. A close second is how well appointed it is, so many things are provided (from a top brand of charcoal for the grills to every kitchen gadget imaginable to robes for the sauna), you really only need to show up with the clothes on your back. The owner, Eric, is responsive and friendly, and the caretakers are equally so. The whole experience is truly a gift!

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Total

Includes taxes and fees
$699+
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