Entire home
Stunning Family/Friends Retreat,110 Private Acres, Renovated Historic Home
Family-friendly stay with in-room kitchens in Madison
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Reviews
10 out of 10
Exceptional
Entire home
5 bedrooms3 bathroomsSleeps 183600 sq ft
Popular amenities
Explore the area

Madison, VA
- Place, Sharp Rock Vineyards16 min drive
- Place, Blue Quartz Winery17 min drive
- Place, Shenandoah National Park28 min drive
- Airport, Charlottesville, VA (CHO-Charlottesville-Albemarle)53 min drive
Room options
About the neighborhood
About this property
Similar properties

Massanutten Resort
McGaheysville
Massanutten Resort
- Pool
- Hot tub
- Spa
- Pet friendly
4.0 out of 5, Very Good, 1,366 reviews
$126 nightly
The price is $139
Jun 15 - Jun 16
Total with taxes and fees
Property amenities
Policies
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 has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm 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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
- This property is managed by a private host, not a professional engaged in trade or business. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock in each accommodation.
Frequently asked questions
Stunning Family/Friends Retreat,110 Private Acres, Renovated Historic Home Reviews
Reviews
10
Exceptional
10/10
Cleanliness
Reviews
Verified
Dec 16, 2025
Liked: Check-in
Stayed 1 night in Nov 2025
Verified
10/10 Excellent
Rachel H.
Nov 13, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Rachel H.
Stayed 3 nights in Nov 2025
Verified
10/10 Excellent
Alicia K.
Jan 10, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Another wonderful stay!
Alicia K.
Stayed 4 nights in Jan 2023
Verified
10/10 Excellent
Chris F.
Sep 22, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Chris F.
Stayed 2 nights in Sep 2025
Verified
10/10 Excellent
Gregory D.
May 16, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing stay!
Gregory D.
Stayed 4 nights in May 2025
Verified
10/10 Excellent
James C.
Oct 14, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing as always !
James C.
Stayed 3 nights in Sep 2024
Verified
10/10 Excellent
Rachel H.
Nov 22, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect Retreat
Rachel H.
Stayed 3 nights in Nov 2024
Verified
10/10 Excellent
michael d.
Feb 18, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Dowd family
michael d.
Stayed 3 nights in Feb 2025
Verified
10/10 Excellent
SEAN K.
Aug 30, 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome vacation
SEAN K.
Stayed 5 nights in Aug 2020
Verified
10/10 Excellent
Matt S.
Jan 6, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Another Great Stay at Whippoorwill!
Matt S.
Stayed 5 nights in Dec 2024
Verified
10/10 Excellent
Wendy K.
Nov 24, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Loved Our Week Away!
Wendy K.
Stayed 7 nights in Nov 2024
Verified
10/10 Excellent
Richard R.
May 9, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing
Richard R.
Stayed 2 nights in Apr 2024
Verified
10/10 Excellent
Maureen T.
Nov 13, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Review
Maureen T.
Stayed 4 nights in Nov 2023
Verified
10/10 Excellent
Kathryn T.
Apr 7, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect escape
Kathryn T.
Stayed 2 nights in Apr 2024
Verified
10/10 Excellent
Rachel H.
Feb 10, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Well provisioned house in a lovely setting
Rachel H.
Stayed 3 nights in Feb 2025
Verified
10/10 Excellent
Holly J.
Aug 18, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
40th bday celebration
Holly J.
Stayed 2 nights in Aug 2024
Verified
10/10 Excellent
Cathy G.
Apr 27, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing Property and Weekend
Cathy G.
Stayed 2 nights in Apr 2023
Verified
10/10 Excellent
Rachel H.
Feb 16, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing weekend
Rachel H.
Stayed 3 nights in Feb 2023
Verified
10/10 Excellent
Brenda W.
Aug 28, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Just as wonderful as i remembered.
Brenda W.
Stayed 3 nights in Aug 2023
Verified
10/10 Excellent
Rachel H.
Nov 7, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fall Retreat
Rachel H.
Stayed 3 nights in Nov 2023
Verified
10/10 Excellent
Matt S.
Jan 8, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Whippoorwill Manor Farm is a special place!
Matt S.
Stayed 5 nights in Dec 2023
Verified
10/10 Excellent
John P.
Aug 13, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fabulous
John P.
Stayed 4 nights in Jul 2024
Verified
10/10 Excellent
Daniel S.
Jun 5, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Peaceful mountain paradise
Daniel S.
Stayed 6 nights in May 2024
Verified
10/10 Excellent
Scott M.
Jul 1, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic Stay
Scott M.
Stayed 7 nights in Jun 2023
Verified
10/10 Excellent
Denice O.
Aug 7, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing Place
Denice O.
Stayed 4 nights in Jul 2024
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