See all properties
Entire home

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

Choose dates to view prices

your current months are December, 2024 and January, 2025.
December 2024
January 2025

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

Outdoor dining
Property grounds
5 bedrooms, iron/ironing board, WiFi, bed sheets
Fridge, microwave, oven, stovetop
TV, fireplace, DVD player, foosball

Reviews

10 out of 10

Exceptional

Entire home

5 bedrooms3 bathroomsSleeps 183600 sq ft

Popular amenities

  • Gym
  • Parking available
  • Washer
  • Barbecue grill
  • Outdoor Space
  • Kitchen

Explore the area

Map
Madison, VA
  • Sharp Rock Vineyards
    11 min drive
  • DuCard Vineyards
    19 min drive
  • Old Rag Mountain
    30 min drive
  • Charlottesville, VA (CHO-Charlottesville-Albemarle)
    47 min drive

Room options

Similar properties

The great room with huge stone fireplace and mountain views.

Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres

Kitchen
Washer
Dryer
Pet friendly
4.7 out of 5, Exceptional, (68)
The price is $698
per night
$1,043 total
includes taxes & fees
Jan 3 - Jan 4
Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres

About the neighborhood

Madison

Located in Madison, this vacation home is in the mountains, within a 15-minute drive of Sharp Rock Vineyards and Blue Quartz Winery. .This family-friendly vacation home is 14.9 mi (24 km) from Shenandoah National Park and 5.8 mi (9.3 km) from DuCard Vineyards.
View more Vacation Homes in MadisonOpens in a new window

What's nearby

  • Sharp Rock Vineyards - 11 min drive
  • Old Rag Mountain - 30 min drive
  • Thorton Gap Entrance Shenandoah - 32 min drive
  • Skyland - 47 min drive
  • Luray Caverns - 49 min drive

Getting around

  • Culpeper Station - 34 min drive
  • Charlottesville-Albemarle Airport (CHO) - 47 min drive

Restaurants

  • ‪Shotwell Run Brew Co L - ‬10 min drive
  • ‪Ducard Vineyards - ‬13 min drive
  • ‪Central Coffee Co. - ‬12 min drive
  • ‪Sparrows Rest - ‬21 min drive
  • ‪La Bella Terra B & B - ‬20 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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

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
Make yourself comfortable in this air-conditioned vacation home, which features a fireplace. There's a private balcony. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Conveniences include a phone, as well as a microwave and a coffee/tea maker.
Be sure to enjoy recreational amenities including a sauna and a fitness center. Additional amenities at this vacation home include an arcade/game room and barbecue grills.
Guests will find features like internet access and onsite parking.

Property manager

Eric Vollmecke

Languages

English

Property amenities

Ski

  • Cross-country skiing nearby

Pool/Spa

  • Sauna

Internet

  • Available in the house: WiFi

Parking and transportation

  • Car required
  • Parking on site

Kitchen

  • Blender
  • Cleaning supplies
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 3 bathrooms
  • Bathtub
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Fireplace
  • Living room
  • Wood stove

Entertainment

  • DVD player
  • Stereo
  • TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Firepit
  • Free firewood
  • Garden
  • Outdoor furniture

Laundry

  • Laundry detergent
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Wheelchair accessibility
  • Smoke-free property

Services and conveniences

  • Iron/ironing board
  • Phone

Location highlights

  • In a rural location
  • In the mountains

Things to do

  • Arcade/game room
  • Bicycles
  • Foosball table
  • Gym
  • Table tennis
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Hunting nearby
  • Kayaking nearby
  • Mountain biking nearby
  • Rock climbing nearby
  • Wildlife walks nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Bicycles
  • Garden
  • Unit size: 3,600 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 26

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets not allowed

Children and extra beds

Children are welcome

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

We should mention

A car is required for transportation to and from this property

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

Reviews

10

Exceptional

Rating 10 - Excellent. 212 out of 214 reviews" "
Rating 8 - Good. 1 out of 214 reviews" "
Rating 6 - Okay. 1 out of 214 reviews" "
Rating 4 - Poor. 0 out of 214 reviews" "
Rating 2 - Terrible. 0 out of 214 reviews" "

10/10

Cleanliness

Reviews

10/10 Excellent

Wendy K.

Liked: Cleanliness
Loved Our Week Away!
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!
Stayed 7 nights in Nov 2024

10/10 Excellent

Rachel H.

Liked: Cleanliness
Perfect Retreat
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!
Stayed 3 nights in Nov 2024

10/10 Excellent

James C.

Liked: Cleanliness
Amazing as always !
We love this place ! I think it’s our 12th year !
Stayed 3 nights in Sep 2024

10/10 Excellent

Emily B.

Liked: Cleanliness
Fantastic stay!
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!
Stayed 4 nights in Sep 2024

10/10 Excellent

John P., Meeker

Liked: Cleanliness
Fabulous
I left a long review earlier.
Stayed 4 nights in Jul 2024

10/10 Excellent

Denice O.

Liked: Cleanliness
Amazing Place
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.
Stayed 4 nights in Jul 2024

10/10 Excellent

Toniann B.

Liked: Cleanliness
Don’t pass this house up!
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!
Stayed 7 nights in Jun 2024

10/10 Excellent

Daniel S., Vienna, Virginia

Liked: Cleanliness
Peaceful mountain paradise
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!
Stayed 6 nights in May 2024

10/10 Excellent

Richard R.

Liked: Cleanliness
Amazing
EVERYTHING we could have possibly needed was available! Beautiful property, beautiful home, cant wait to come back! Accommodated a bunch of ICU nurses and our families perfectly!
Stayed 2 nights in Apr 2024

10/10 Excellent

Andrew P.

Liked: Cleanliness
Bachelor Party Getaway
This was everything a group of 20s-30s guys could ask for in a location to get together and relax. Ladies weren’t there, but I’m sure they would have loved it too. Perfect location. Beautiful scenery. Wonderful lookout for morning coffee. Fire pit, games, sprawling lawn, access to hiking and dirt biking trails, big kitchen full of appliances. Great showers. Sauna. Far enough away to feel like an adventure, but close enough to be convenient. Everything was spotless on arrival. The whole property was full of amenities and extra little touches to make things more convenient. Great host. Very easy to communicate with. 10/10 would recommend for any occasion.
Stayed 2 nights in Apr 2024

10/10 Excellent

Kathryn T.

Liked: Cleanliness
Perfect escape
We thoroughly enjoyed our stay at this lovely property. The house is so nice, the kitchen is so well appointed, they have thought of everything you might need. The range of activities was so fun from pickle ball, to darts, ping pong etc. we loved sitting at the deck at the top of the hill with the beautiful view of the mountains.
Stayed 2 nights in Apr 2024

10/10 Excellent

Matt S., Richmond, VA

Liked: Cleanliness
Whippoorwill Manor Farm is a special place!
I stayed with my family (11 in total), ranging from 8 to almost 80 years old. Whippoorwill was a truly unique property, and experience, for us all. The home and area are beautiful and there's so much to see and do on the property. The home is incredibly well-stocked and the owner was fantastic to work with. We'll definietly return. Highly recommend!
Stayed 5 nights in Dec 2023

10/10 Excellent

Maureen T.

Liked: Cleanliness
Review
Absolutely wonderful!!
Stayed 4 nights in Nov 2023

10/10 Excellent

Rachel H.

Liked: Cleanliness
Fall Retreat
Whippoorwill is a wonderful property and perfect for our group of 10 people. The foliage was still brilliant and the weather was nice enough for us to grill one day. They have everything you could possibly want for cooking and recreation. The host and caretakers are very easy to get in touch with and are lovely people. We highly recommend this property!
Stayed 3 nights in Nov 2023

10/10 Excellent

karen D.

Liked: Cleanliness
Fall gathering with friends
The Whippoorwill Manor Farm was true to the photos as a beautifully and thoughtfully restored farm house and property, perfectly situated in the blue ridge mountains. So quiet and peaceful! It was ideal for our group of nine, and could clearly accomodate more guests very easily. There are plenty of physical activities if desired, including hiking both on and off the property. The pickleball court got some spirited use! The farm is also a place to simply sit, relax, and enjoy, with comfortable seating both inside and out. The farm kitchen is fully equipped, and there was ample seating to share meals at the indoor or outdoor tables. Recommend taking in the sunset on the upper platform, We had a campfire under the stars each night. Eric could not be a more responsive host, and he takes care of his guests in every way. I would unhesitatingly recommend this property to any group, of any age!
Stayed 3 nights in Oct 2023

10/10 Excellent

Brenda W.

Liked: Cleanliness
Just as wonderful as i remembered.
Our group of 13 ladies returned after 8 years for a weekend to recharge physically, mentally and spiritually. We wandered through the woods, enjoyed the pickle ball court and cooked great healthy meals in the very well-stocked kitchen. This farm is definitely a place of retreat!
Stayed 3 nights in Aug 2023

10/10 Excellent

Scott M.

Liked: Cleanliness
Fantastic Stay
We had a great time at the Whippoorwill Manor Farm. The property is amazing and the hosts and caretakers were great. The hosts have thought of everything in terms of amenties. The kitchen is well stocked with appliances, utensils and tools, and dishes, and the ice maker is a nice touch. Outside we enjoyed the sauna, game room, fire pit, ping pong table, bicycles, pickelball court, basketball court, hiking trails...all of it. Hope to return soon!
Stayed 7 nights in Jun 2023

10/10 Excellent

Cathy G.

Liked: Cleanliness
Amazing Property and Weekend
The property is spectacular. The house is well stocked, comfortable and had everything (and more!) than we needed. There was a ton to do on the property itself and hiking was a 20 minute drive. We will definitely be back again!
Stayed 2 nights in Apr 2023

10/10 Excellent

Rachel H.

Liked: Cleanliness
Amazing weekend
The house and property are amazing. The host has made check in and out very clear and is very easy to get a hold of and communicate with. My friends and I held a chamber music weekend and had a wonderful time playing and using the amazing kitchen. We’ll probably be booking again this year!
Stayed 3 nights in Feb 2023

10/10 Excellent

Alicia K.

Liked: Cleanliness
Another wonderful stay!
We love Whippoorwill and how well the property is managed!
Stayed 4 nights in Jan 2023

10/10 Excellent

Alicia K.

Liked: Cleanliness
Still the best!
We try to come to Whippoorwill Manor Farm at least once a year. Every year new amenities are added and the house is well kept and clean. We absolutely love visiting and hope to be back many times in the future. This time we did a lot of cooking indoors, and they had every piece of equipment we needed. The owner/property manager is a super efficient communicator. Thank you for providing such an amazing place to build more memories!
Stayed 4 nights in Dec 2022

10/10 Excellent

Tammy H., Cary, North Carolina

Liked: Cleanliness
The PERFECT getaway retreat!
We stayed here as a family and made this our home base for my son's wedding. It could NOT be a more perfect place to stay and we definitely want to come back another time. The house is very spacious and fully stocked with everything you could possibly need and more. You will not regret staying here!
Stayed 4 nights in Oct 2022

10/10 Excellent

Chris C., Annapolis

Liked: Cleanliness
'Yellow House' never disappoints
We've lost count of how many times we have enjoyed 'Yellow House' as we call it. For over 10 years, we have gathered with friends and family at this special place and it has never disappointed us.
Stayed 3 nights in Sep 2022

10/10 Excellent

Tammy H.

Liked: Cleanliness
Family Vacay
This property was awesome. It provided a clean, warm and nurturing environment for a treasured family vacation. We took family pictures with the beautiful background provided by the farm. Loved every minute spent here!
Stayed 7 nights in Jul 2022

10/10 Excellent

John F.

Liked: Cleanliness
Fantastic Stay
We had a lovely time at this property. The location was breathtaking and so very peaceful- a nice escape from our normal lives in the busy city! We were together for my parents’ 40th anniversary and there were plenty of activities nearby (wineries, hiking, Shenandoah NP, etc) but also plenty to do at the rental- hiking, ping pong, shuffleboard, basketball, darts, corn hole, honestly any game you could probably think of. We had a great time hanging out with the surrounding nature and Eric was extremely helpful and responsive every step of the way. Would definitely recommend this magical place!
Stayed 7 nights in Jul 2022