Entire home

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

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

A wooden pergola with a table and benches, a small shed, and a hill with a house in the background.
A large, single-story house with a green roof, surrounded by lush greenery and a small red barn.
A wooden-framed bed with a quilted green bedspread and multiple pillows, a bedside table with a lamp, and a fireplace with a framed picture above it.
A log cabin interior with a fireplace, a television, and a cozy seating area with sofas and a red ottoman.
A kitchen with wooden cabinets, stainless steel appliances, and a black countertop.

Reviews

10 out of 10
Exceptional

Highlights

  • Family fun awaits
    Top-rated for families.
  • Arcade/game room
    A rare find - fun for all ages with on-site arcade/game room.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Balcony
  • On-site fitness center
  • Arcade/game room
  • Barbecue grill
  • Air conditioning
  • Washer

Explore the area

View in a map
Madison, VA
  • Place, Sharp Rock Vineyards
    ‪16 min drive‬
  • Place, Blue Quartz Winery
    ‪17 min drive‬
  • Place, Shenandoah National Park
    ‪28 min drive‬
  • Airport, Charlottesville, VA (CHO-Charlottesville-Albemarle)
    ‪53 min drive‬

Rooms & beds

5 bedrooms (sleeps 18)

Bedroom 1

1 Queen Bed and 1 Crib

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed

Bedroom 4

+2
4 Double Beds and 2 Twin Bunk Beds

Bedroom 5

+1
4 Twin Beds and 1 Queen Bed

Sunroom

1 King Bed

3 bathrooms

Bathroom 1

Toilet · Shower only

Bunkroom

Bathtub · Toilet · Shower only

Upstairs Hallway

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Garden
Dining area

Add dates for prices

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About the neighborhood

Madison

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 hiking and horse riding nearby.
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Map
Madison, VA

What's nearby

  • Sharp Rock Vineyards - 16 min drive - 12.0 km
  • Blue Quartz Winery - 17 min drive - 10.3 km
  • Madison Plaza - 23 min drive - 24.8 km
  • Copper Fox Distillery - 24 min drive - 27.9 km
  • Shenandoah National Park - 28 min drive - 33.1 km

Getting around

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

Restaurants

  • ‪Freekick - ‬25 min drive
  • ‪La Bella Terra B & B - ‬19 min drive
  • ‪Graves Mountain Lodge - ‬25 min drive
  • ‪Central Coffee Co Limited - ‬12 min drive
  • ‪Sparrows Rest - ‬21 min drive

Frequently asked questions

Is Stunning Family/Friends Retreat,110 Private Acres, Renovated Historic Home pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Stunning Family/Friends Retreat,110 Private Acres, Renovated Historic Home?

As of Nov 10, 2026, prices found for a 1-night stay for 2 adults at Stunning Family/Friends Retreat,110 Private Acres, Renovated Historic Home on Nov 11, 2026 start from $793, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Stunning Family/Friends Retreat,110 Private Acres, Renovated Historic Home?

Check-in begins at 4:00 PM.

What time is check-out at Stunning Family/Friends Retreat,110 Private Acres, Renovated Historic Home?

Check-out is at 11:00 AM.

Where is Stunning Family/Friends Retreat,110 Private Acres, Renovated Historic Home located?

Located in the mountains, this family-friendly vacation home is within 6 mi (10 km) of Blue Quartz Winery, Sharp Rock Vineyards, and DuCard Vineyards. Madison Plaza and Lawrence Beasley Park are also within 12 mi (20 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 226 out of 228 reviews
Rating 8 - Good. 1 out of 228 reviews
Rating 6 - Okay. 1 out of 228 reviews
Rating 4 - Poor. 0 out of 228 reviews
Rating 2 - Terrible. 0 out of 228 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our group of family friends has a wonderful time on the property for the weekend! So many thoughtful touches that made for a convenient stay. Thank you!
Stayed 3 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a fantastic stay at aWhipporwhill as always! We had a great time enjoying everything the property had to offer- hiking, games, sauna, relaxing on the overlook, and grilling. This is the best equipped (and labeled) rental with everything you need to enjoy the property. We have stayed here 5 times and will certainly be back again!
Stayed 3 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Another wonderful stay!

We love Whippoorwill and how well the property is managed!
Stayed 4 nights in Jan 2023
Verified review

10/10 Excellent

Liked: Check-in
Excellent
Stayed 1 night in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing stay!

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.
Stayed 4 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This beautiful home was perfect for our large family. (Yep, all the beds were full). Yet we were very comfortable. Clean and spacious! We stayed here 5 years ago and since then a swing set and play house with a sand box was added. The house has everything you could need inside and outside. Basketball, pickleball, horseshoes, fire pit, sauna etc etc. The communication was great from the owner right down to maintenance and cleaning who we had to contact because we forgot something. Usually once you checkout no one calls you back so that deserves an extra 5 stars. Hope to return and stay again.
Stayed 5 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 3 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 2 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome vacation

Had an amazing time down there with our friends. The house and property far exceeded my expectations. Looking forward to returning as soon as we can. Great owner, great experience.
Stayed 5 nights in Aug 2020
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing as always !

We love this place ! I think it’s our 12th year !
Stayed 3 nights in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Dowd family

Everything was perfect. Everything you could possibly need was there. Great experience would definately return
Stayed 3 nights in Feb 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Another Great Stay at Whippoorwill!

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!!
Stayed 5 nights in Dec 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Review

Absolutely wonderful!!
Stayed 4 nights in Nov 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

40th bday celebration

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!
Stayed 2 nights in Aug 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Well provisioned house in a lovely setting

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!
Stayed 3 nights in Feb 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fabulous

I left a long review earlier.
Stayed 4 nights in Jul 2024
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