House in Shenandoah Valley, VA
6 guests · 2 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
High-end valueWell priced for this area
About this house rental
This is your opportunity to spend a weekend at one of the most historic and private homes in Orange VA. This is the former residence of James Madison’s brother Ambrose Madison est 1783. The estate features 50+ acres of open fields and stream, 3 private ponds, walking trails, gorgeous sunset views, and was featured on the 2012 Garden Club of Virginia Historic Garden Week Tour.
Come experience the country side in this modern guest cottage. Complete with full kitchen, 2 bedrooms featuring a king size bed downstairs and 2 twin beds upstairs, 2 full bathrooms with walk in shower, living room, screened in porch, patio, private parking, and media area with cable TV. The cottage will sleep four very comfortably, over 1000+ square feet.
Minutes from Woodberry Forest School and downtown Orange, 8 Minutes to best main street in VA Gordonsville, 25 minutes from Charlottesville, UVA and Scott Stadium, this is an ideal setting for a private getaway. The property has a central location in the up and coming Virginia Wine region; quickly becoming the Napa Valley of the east coast. Property has great fishing in the private ponds, manicured grounds, guided hunting, golf outings, and Wine Tours. The owners are local and can serve as great advisers and historians of the area. There are many local museums such as Montpelier, civil war battlefields, restaurants, antiquing and history to explore.
Want to live on the wild side? Orange offers the opportunity to go sky diving! We look forward to your visit.
Come experience the country side in this modern guest cottage. Complete with full kitchen, 2 bedrooms featuring a king size bed downstairs and 2 twin beds upstairs, 2 full bathrooms with walk in shower, living room, screened in porch, patio, private parking, and media area with cable TV. The cottage will sleep four very comfortably, over 1000+ square feet.
Minutes from Woodberry Forest School and downtown Orange, 8 Minutes to best main street in VA Gordonsville, 25 minutes from Charlottesville, UVA and Scott Stadium, this is an ideal setting for a private getaway. The property has a central location in the up and coming Virginia Wine region; quickly becoming the Napa Valley of the east coast. Property has great fishing in the private ponds, manicured grounds, guided hunting, golf outings, and Wine Tours. The owners are local and can serve as great advisers and historians of the area. There are many local museums such as Montpelier, civil war battlefields, restaurants, antiquing and history to explore.
Want to live on the wild side? Orange offers the opportunity to go sky diving! We look forward to your visit.
Amenities at One of Central Virginia's most historic Private Guest Residences
Non-smoking
Pets allowed
Family friendly
Map of Shenandoah Valley, VA
Ratings and reviews
Summary of reviewsBeautiful property with comfortable bedrooms and a relaxing screened patio. Incredibly attentive property manager. Fabulous stay amidst splendid views and modern comforts. Highly recommended!
10 / 10Outstanding·Dec 2025
The house is beautiful, in a lovely country setting.The furnishings and decor are appropriate to the history of the house, which is fascinating if you’re a history buff!It was clean and well appointed, with a modern kitchen and two en suite bathrooms to go with the two bedrooms. The bedroom upstairs has its own sitting room with a tv; there’s no tv downstairs.We loved it! PS: Please note: There is no drinking from the faucets; but fresh bottled water is supplied.
10 / 10Outstanding·Oct 2025
Everything was excellent! Enjoyed our stay very much! Would come again!
10 / 10Outstanding·Jul 2025
Our stay at Woodley Cottage was wonderful! Extremely clean, beautifully decorated, and comfortable for our family of 4. The property has a lovely drive in and the scenic views from the cottage are beautiful! We definitely enjoyed our stay.
10 / 10Outstanding·Jun 2025
Felt like we stepped back into history. Was lovely. And the quiet peaceful property was just what we needed.
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Top rated by guests
9.9Outstanding
(102 Ratings)
Beautiful property with comfortable bedrooms and a relaxing screened patio. Incredibly attentive property manager. Fabulous stay amidst splendid views and modern comforts. Highly recommended!
From real guest reviews summarized by AIDon't miss out! Price and availability may change
