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One of Central Virginia's most historic Private Guest Residences

Photo gallery for One of Central Virginia's most historic Private Guest Residences

A spacious living room with hardwood floors, a sofa, a coffee table, and a staircase leading to a balcony.
A dining area with a wooden table, chairs, and a stone wall backdrop.
A house with a large porch and a covered area, surrounded by a grassy yard and trees.
A covered porch with a blue chair, a wicker chair, and a table.
A bedroom with a four-poster bed, a stone fireplace, and a wooden dresser.

Reviews

10 out of 10
Exceptional

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
Sleeps 6•2 bedrooms•2 beds

Popular amenities

  • Onsite parking available
  • Pet-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue

Explore the area

View map
Orange, VA
  • Place, Honah Lee Vineyard
    ‪3 min drive‬
  • Place, St. Thomas Episcopal Church
    ‪7 min drive‬
  • Place, The Arts Center in Orange
    ‪7 min drive‬
  • Airport, Charlottesville, VA (CHO-Charlottesville-Albemarle)
    ‪34 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

2 Single Beds

2 bathrooms

Bathroom 1

Bathroom 2

Spaces

Deck or patio
Kitchen
Dining area

About this property

One of Central Virginia's most historic Private Guest Residences

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.

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House Rules

Check in after 4:00 PM
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 431500vb
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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
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

About the area

Orange

Orange is home to this holiday home. Honah Lee Vineyard and Horton Vineyards are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Lake Anna and Rapidan River. Discover the area's water adventures with nearby fishing, or enjoy the great outdoors with horse riding, hunting and mountain biking.
View more Holiday homes in OrangeOpens in a new window
Map
Orange, VA

What's nearby

  • Honah Lee Vineyard - 3 min drive - 3.4 km
  • James Madison Museum - 7 min drive - 6.9 km
  • St. Thomas Episcopal Church - 7 min drive - 7.2 km
  • The Arts Center in Orange - 7 min drive - 7.6 km
  • James Madison's Montpelier - 15 min drive - 14.8 km

Getting around

  • Charlottesville, VA (CHO-Charlottesville-Albemarle) - 37 min drive

Restaurants

  • ‪McDonald's - ‬6 min drive
  • ‪Domino's Pizza - ‬6 min drive
  • ‪Patch Brewing Co. - ‬9 min drive
  • ‪Hardee's - ‬6 min drive
  • ‪The Main Street Tavern - ‬6 min drive

Frequently asked questions

Is One of Central Virginia's most historic Private Guest Residences pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at One of Central Virginia's most historic Private Guest Residences?

As of 2 August 2026, prices found for a 1-night stay for 2 adults at One of Central Virginia's most historic Private Guest Residences on 9 August 2026 start from NZ$1,043, 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 at One of Central Virginia's most historic Private Guest Residences?

On-site parking is available at the property.

What time is check-in at One of Central Virginia's most historic Private Guest Residences?

Check-in begins at 4:00 PM.

What time is check-out at One of Central Virginia's most historic Private Guest Residences?

Checkout is at 10:00 AM.

Where is One of Central Virginia's most historic Private Guest Residences located?

Situated in Orange, this holiday home is 2.2 mi (3.6 km) from Honah Lee Vineyard and within 6 miles (10 km) of James Madison Museum and St. Thomas Episcopal Church. The Arts Center in Orange and James Madison's Montpelier are also within 6 miles (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 98 out of 104 reviews
Rating 8 - Good. 4 out of 104 reviews
Rating 6 - Okay. 1 out of 104 reviews
Rating 4 - Poor. 1 out of 104 reviews
Rating 2 - Terrible. 0 out of 104 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

David O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was excellent! Enjoyed our stay very much! Would come again!
Stayed 2 nights in Oct 2025
Verified review

10/10 Excellent

Michelle S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
A Truly Special Stay in a Historic Virginia Gem…Staying here is an experience I will be talking about for a long time. This property blends beautifully preserved history with modern comfort, creating a stay that feels both meaningful and luxurious.From the moment I arrived, I could feel the character of the place, the architecture, the grounds, and all the thoughtful details all speak to its long rich history. The residence was spotless, well appointed, and clearly cared for with pride. The beds were incredibly comfortable, the linens and towels were high quality. I especially loved the “makeup” washcloth. I enjoyed sipping coffee and wine on the screened in porch overlooking the property. The grounds are exceptional. The hosts were exceptional: responsive, welcoming, full of information about the area, its wineries and the history. They struck the perfect balance between giving privacy and being available when needed.If you are looking for a stay that is more than just a place to sleep- something with soul, beauty, and a sense of peace- this residence is a standout. I am looking forward to my next visit.
Stayed 4 nights in May 2026
Verified review

10/10 Excellent

Suzanne D.

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

10/10 Excellent

Faerlie H.

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

Wedding Stay

We were in town for a family wedding and this was the perfect spot for us to stay! The property is beautiful and the owners were very kind to let us fish in their ponds as well, it made the trip for my husband and I!
Stayed 3 nights in Apr 2025
Verified review

10/10 Excellent

David E.

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

Wonderful

Amazing stay
Stayed 4 nights in Sep 2023
Verified review

10/10 Excellent

Patricia H.

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

Weekend Getaway

Updated historic cabin that was very convenient to local attractions.
Stayed 2 nights in May 2024
Verified review

10/10 Excellent

Chris T.

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

Woodberry Forest Visit

Great place for WFS parents weekend visit. Had everything we needed and was in a good location.
Stayed 2 nights in Oct 2023
Verified review

10/10 Excellent

Elizabeth F.

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

Charming guest house

In beautiful farm surroundings
Stayed 2 nights in Nov 2024
Verified review

10/10 Excellent

Helen P.

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

Beautiful property

Beautiful property and home
Stayed 11 nights in Sep 2024
Verified review

10/10 Excellent

Stina Marie S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 4 nights in Dec 2025
Verified review

10/10 Excellent

Mary M.

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

Attending local women’s event

Felt like we stepped back into history. Was lovely. And the quiet peaceful property was just what we needed.
Stayed 4 nights in Jun 2025
Verified review

10/10 Excellent

Cary C.

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

Travel back in history!

Wonderful stay! Great property and location. Host is very responsive and conscientious of the property. We would stay there again.
Stayed 5 nights in Nov 2023
Verified review

10/10 Excellent

Nan M.

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

Woodley Cottage

Fantastic place to stay. Thank you.
Stayed 3 nights in Jun 2023
Verified review

10/10 Excellent

John W.

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

Great, great, great stay

This cottage was a fabulous get away. We think this was one of the best VRBOs we have ever stayed. Wonderful all around and the owner was super accommodating in every way. Highly recommend!
Stayed 3 nights in Mar 2024
Verified review

10/10 Excellent

Lynn A.

Lovely cottage

The host was very welcoming and responsive. The cottage is well equipped, my family and I had a wonderful stay!
Stayed 6 nights in Nov 2018
Verified review

10/10 Excellent

Nicole J.

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

Cozy little cottage

We loved our stay at the cottage. Kids loved the upstairs and the master bedroom was spacious and comfy. Kitchen was stocked for cooking and views were perfect. It was a great place to end our days after our Virginia trip!
Stayed 5 nights in Jun 2023
Verified review

10/10 Excellent

James S.

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

Great home in a serene location

Had a great time in the area, the house and grounds were perfect, we took our dogs on long walks every day without ever taking them off the property. The host was a great resource for things to do in the area.
Stayed 4 nights in Dec 2022
Verified review

10/10 Excellent

Mary L.

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

Excellent Stay

Immaculate and well appointed. It is perfect for a couple or a family with one or two children. We were there for a weekend visit and will definitely return.
Stayed 2 nights in Nov 2023
Verified review

10/10 Excellent

Susan G.

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

Beautiful cottage in amazing location

The cottage was beautiful in every way. The furnishings were both lovely and comfortable. The living areas were spacious. The kitchen was well equipped. The bed was great. Everything was extremely clean. The screen porch overlooking the gorgeous grounds was the icing on a perfect stay.
Stayed 3 nights in Apr 2025
Verified review

10/10 Excellent

Sally T.

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

Perfect Cottage

Two night getaway in a lovely cottage in a perfect setting. Everything was wonderful especially the bed linens and towels. Highly recommend!
Stayed 2 nights in Apr 2023
Verified review

10/10 Excellent

Jennifer K.

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

Great dc getaway

Wonderful stay overall. For three days, we had a great time exploring the area while our two year old golden retriever lived his best life. Gorgeous property. We will definitely be back.
Stayed 2 nights in Sep 2023
Verified review

10/10 Excellent

James B.

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

Visit Virginia

Very nice cottage. Very clean. Very comfortable and relaxing.
Stayed 4 nights in Apr 2024
Verified review

10/10 Excellent

Lynn C.

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

A true stay in a historical cottage

Wonderful historic home from1738. Loved letting our little dog run around the grounds. The huge fireplaces, antique furniture, modern kitchen made it an absolutely wonderful home away from home.
Stayed 4 nights in Oct 2023
Verified review

10/10 Excellent

David H.

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

Beautifully restored home

Beautiful property and wonderful stay. Lots of land for our dogs to roam about. House itself was cozy and private. Lots of wineries, historical attractions, and nature trails nearby. Wonderful place to disconnect and spend time together.
Stayed 3 nights in Feb 2023
Archival

10/10 Excellent

Peary P.

Great location

We came up for Parent's Weekend as our son is in school nearby. The house was great and even had a washer/dryer combo so we could do a little laundry. The owner was lovely to work with and was very accommodating! We're looking forward to our next stay.

About the host

Hosted by Richard Sanford

Host profile image
The owners are native and have a vast knowledge of the area, including, restaurants, shopping, wineries, restaurants, history, museums, civil war batttlefields, and antique stores, and auctions.

Why they chose this property

The history, the ambiance, the peaceful and quite tranquil clean air of country living. The home features all the modern amenities one would expect without the bother of people coming and going from a hotel setting. This is as private a setting as you will find in the area.

What makes this property unique

Full Kitchen, hardwood floors, central location.
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