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

Family-friendly holiday home with fitness centre and sauna

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

Outdoor dining - Stunning Family/Friends Retreat,110 Private Acres, Renovated Historic Home (Madison)
Fridge, microwave, oven, stovetop - Stunning Family/Friends Retreat,110 Private Acres, Renovated Historic Home (Madison)
TV, fireplace, DVD player, table football - Stunning Family/Friends Retreat,110 Private Acres, Renovated Historic Home (Madison)
Exterior - Stunning Family/Friends Retreat,110 Private Acres, Renovated Historic Home (Madison)
5 bedrooms, iron/ironing board, WiFi, bed sheets - Stunning Family/Friends Retreat,110 Private Acres, Renovated Historic Home (Madison)
Escape to Whippoorwill Manor Farm, a serene destination nestled near Old Rag Mountain. This historic farm home with log cabin charm offers a unique retreat for family and friends, featuring wide hickory planked floors, stone fireplaces, and handcrafted woodwork throughout the home. The property also includes modern conveniences like direct TV and wireless internet.

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms3 bathroomsSleeps 183600 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
  • Gym
  • Outdoor space

Add dates for prices

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

Family-friendly holiday home with fitness centre and sauna
Along with a fitness centre, this smoke-free holiday home has a sauna and laundry facilities. Additionally, an arcade/games room, a garden and barbecues are on-site. The holiday home has 5 bedrooms and offers a DVD player and a balcony. Guests can enjoy a fireplace, and other amenities include a kitchen with a fridge and an oven.
Air-conditioned accommodation at this holiday home offers fireplaces and DVD players. Rooms open to balconies. Kitchens offer fridges, stovetops, microwaves and kitchenware and utensils.

Bathrooms include a shower and hairdryers. Additionally, rooms include coffee/tea makers and an iron/ironing board.

Recreational amenities at the holiday home include a sauna and a fitness centre.

The recreational activities listed below are available either on-site or nearby; fees may apply.

Property amenities

Ski

  • Cross-country skiing nearby

Pool/Spa

  • Sauna

Internet

  • Available in the house: WiFi

Parking and transport

  • Car required
  • Parking on site

Kitchen

  • Blender
  • Cleaning supplies
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • 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
  • Laundry facilities
  • 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.
  • In-room 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

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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
Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
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 transport to and from this property

About the area

Located in Madison, this holiday home is in a rural area and in the mountains. The area's natural beauty can be seen at Shenandoah National Park and Thorton Gap Entrance Shenandoah, while River District Arts and Glassworks Gallery are cultural highlights. Kayaking and fishing offer great chances to get out on the surrounding water, or you can seek out an adventure with rock climbing and hunting nearby. Visit our Madison travel guide
View more Holiday homes in Madison
Map
Madison, VA

What's nearby

  • Weinberge in der Nahe-Region im Herbst bei Wallhausen auf dem Premium-Wanderweg Vitaltour Stein, Wein & Farbe im Landkreis Bad Kreuznach in der Nahe-Region von Rheinland-Pfalz.
    Sharp Rock Vineyards
    15 min drive - 12.0 km
  • Early Mountain Vineyards is hands down one of the best in Virginia. It has a wonderful setting with large outside seating area, gas fireplace, live music and incredible view. Owned by AOL founder Steve Case, this vineyard offers tastings of wines from all over Virginia. Try one of their many tasting wine flights!
    Early Mountain Vineyards
    24 min drive - 28.9 km
  • Shenandoah National Park showing a river or creek and forests as well as a couple
    Shenandoah National Park
    27 min drive - 32.1 km
  • Blue Quartz Winery
    11 min drive - 7.9 km
  • DuCard Vineyards
    21 min drive - 11.0 km

Getting around

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

Restaurants

  • Shotwell Run Brew Co L
    10 min drive
  • Ducard Vineyards
    13 min drive
  • La Bella Terra B & B
    19 min drive
  • Graves Mountain Lodge
    25 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 is parking at Stunning Family/Friends Retreat,110 Private Acres, Renovated Historic Home?

On-site 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?

Checkout 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 holiday 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 miles (20 km).

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

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 221 out of 223 reviews
Rating 8 - Good. 1 out of 223 reviews
Rating 6 - Okay. 1 out of 223 reviews
Rating 4 - Poor. 0 out of 223 reviews
Rating 2 - Terrible. 0 out of 223 reviews

10

Cleanliness

10

Location

Reviews

10/10 Excellent

Chris F.

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

10/10 Excellent

Gregory D.

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

10/10 Excellent

Rachel H.

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

10/10 Excellent

Matt S.

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

10/10 Excellent

Wendy K.

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

10/10 Excellent

Rachel H.

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

10/10 Excellent

Kathryn T.

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

10/10 Excellent

Holly J.

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

10/10 Excellent

Daniel S.

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

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

Denice O.

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

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

Andrew P.

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

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

Toniann B.

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

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

karen D.

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

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

Emily B.

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

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

Rachel H.

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

10/10 Excellent

Alicia K.

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

10/10 Excellent

michael d.

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

10/10 Excellent

James C.

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

10/10 Excellent

SEAN K.

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

10/10 Excellent

Richard R.

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

10/10 Excellent

Maureen T.

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

Review

Absolutely wonderful!!
Stayed 4 nights in Nov 2023

10/10 Excellent

Cathy G.

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

10/10 Excellent

Rachel H.

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

10/10 Excellent

Brenda W.

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

10/10 Excellent

Rachel H.

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