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One of Central Virginia's most historic Private Guest Residences

Holiday home in Orange with kitchen and patio

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

Exterior
Exterior
Exterior
Private kitchen
Private kitchen

Reviews

10 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 692.9 sq m

Popular amenities

  • Dryer
  • Parking available
  • Washer
  • Fireplace
  • Kitchen

Explore the area

View map
Orange, VA
  • Place, St. Thomas Episcopal Church
    ‪7 min drive‬
  • Place, The Arts Center in Orange
    ‪8 min drive‬
  • Place, James Madison's Montpelier
    ‪18 min drive‬
  • Airport, Charlottesville, VA (CHO-Charlottesville-Albemarle)
    ‪43 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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Amenities

Kitchen
Washing machine
Dryer
Pet-friendly
Air conditioning
Outdoor space

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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

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

We should mention

A car is recommended for transport to and from this property

About the area

Orange

Orange is home to this holiday home. James Madison's Montpelier and Barboursville Ruins are local landmarks, and some of the area's activities can be experienced at Honah Lee Vineyard and Horton Vineyards. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
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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 - 8 min drive - 7.6 km
  • James Madison's Montpelier - 18 min drive - 14.8 km

Getting around

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

Restaurants

  • ‪McDonald's - ‬6 min drive
  • ‪Harvest Coffee - ‬6 min drive
  • ‪Rick's Fried Chicken - ‬7 min drive
  • ‪Hardee's - ‬6 min drive
  • ‪Iron Pipe Alewerks - ‬7 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.

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. 94 out of 99 reviews
Rating 8 - Good. 4 out of 99 reviews
Rating 6 - Okay. 0 out of 99 reviews
Rating 4 - Poor. 1 out of 99 reviews
Rating 2 - Terrible. 0 out of 99 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

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

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

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

10/10 Excellent

Nancy R.

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

The most charming cottage.

We will be back! Our stay was amazing and just as advertised. Everything you could need they provide. One of the cutest places we’ve stayed! The owners are very quick to reply with any questions. I was there alone with my daughter and a few of her friends and we felt very safe. Thank you for an amazing stay!
Stayed 2 nights in Jan 2025

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

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

10/10 Excellent

Andrew T.

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

Amazing find!

Beautiful property! Very comfortable bedrooms, set up perfectly for our family of 3. The screened patio is a special spot to relax. Property manager was incredibly attentive. We will be back!
Stayed 4 nights in May 2024

10/10 Excellent

Dana E.

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

Wry charming farm cottage

We really enjoyed staying at this unique property that dates to the 1700s! It’s been thoughtfully remodeled and is very clean and comfortable. We were in t area looking at colleges and it suited our needs perfectly!
Stayed 2 nights in Apr 2023

10/10 Excellent

Marguerite O.

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

Historic Gem in Pastoral Setting

We found this to be a private, clean and well appointed location - wonderful for our two dogs. Communication with the host was excellent. Overall it was a delightful stay. Thank you.
Stayed 7 nights in Mar 2023
This review was submitted before 2018 and has not been verified.

8/10 Good

Leslie G.

Beautifully refinished old summer kitchen

Very nice accommodations. Lovely grounds & better than any hotel. We love history, wish there was more history of the cottage & pictures of before and after the renovation. Could have done a little better job clearing cob webs & spiders before stay our stay, but overall loved it.
Stayed 2 nights in Jun 2017

10/10 Excellent

Mary H.

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

Lovely Cottage on Gorgeous Property - an All-round Winner!

If you find yourself anywhere in the Orange, Gordonsville, Barboursville VA area, this is a FANTASTIC rental. Great location, wonderful hosts, lovely cottage. We came for a birthday weekend, to be close to Barboursville Vineyards (our wine fave), and as cyclists, to ride the backroads of Orange County. This location made both goals a joy to reach. The house is nicely appointed - nothing chinzy. Comfortable king bed, fluffy towels, stocked kitchen. And as amateur astronomers, we LOVED the dark skies. Lovely views over the meadows, and beautiful landscaping of flowers attracting butterflies. Just a wonderful, relaxing place to stay.
Stayed 2 nights in Jul 2024

10/10 Excellent

Chrystal K.

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

Virginia exploration

Very nice stay. Cottage was very clean and nicely updated. Loved the 18th century ambience. We used the location to pivot from each day so we could explore DC, Norfolk, Jamestown, Monticello, Montpelier, and Shenandoah national park. Overall a busy trip, but a fun one. Kids enjoyed having the upstairs to themselves, away from mom/dad on the first floor. Also enjoyed walking the 1 mile loop around the property at night. Overall, a very pretty setting.
Stayed 7 nights in Mar 2023

10/10 Excellent

Donald W., Saint Louis, Missouri

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

Charming Cottage

We spent two nights at this charming cottage while visiting local wineries and the nearby towns of Orange and Gordonsville. The cottage is a restored and renovated summer kitchen for the adjacent Woodley estate. This was the home of Ambrose Madison, brother of President James Madison. The cottage provides a “colonial” America feel with all the modern 21st Century conveniences. There are two spacious bedrooms each with its own full bathroom, kitchen, two large sitting areas and a dining area. Included is a screened porch with views of the lovely countryside from which to enjoy morning coffe or evening wine. All four of our party would definitely return in the future.
Stayed 2 nights in Jun 2023

10/10 Excellent

Lisa H.

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

Cozy historic cottage in the lap of Mother Nature

This beautiful property, surrounded by the most splendid Blue Ridge farmland views offered so much to nurture two weary sister mamas who needed the respite of its special peace and quiet. This immaculately kept, 2-story historic little house offered the perfect blend of comfortably furnished gathering areas, modern creature comforts and privacy. Well-working new kitchen fixtures, appliances and Wi-Fi, a beautifully appointed en suite bathroom downstairs and perfectly working HVAC made for an idyllic, comfy retreat. The surrounding land and its romantically imagined plantings, including weeping willows on ponds and redbud trees lining a long, curved driveway invited wildlife sightings to delight. Staying pre-Spring, early daffodils were popping and a giggling creek complete with gently laughing waterfalls added to our enjoyment. Hope to stay again and warmly recommend. 💐
Stayed 3 nights in Feb 2024
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Lyla R., Oklahoma City, OK

Heavenly Stay in Orange

We were thrilled with every aspect of our recent stay at Woodley Cottage in Orange, Virginia. The owner was very helpful with our reservation. We were arriving late in the evening and didn't have a clue where we were going. GPS got us to the home and we found it warmly lit and inviting after our long day of travel. The cottage was absolutely delightful and so comfortable for our group, my husband and me plus our son, daughter-in-law and 17 month old grandson. It truly was a home away from home. We didn't get to see much of the grounds until the next morning. We were in for a real treat...rolling hills, tree lined drives, ponds, a waterfall, cattle on the adjacent land, and wheat harvesting! Our grandson was amazed, which made our stay so enjoyabe. The cottage had everything we needed for a perfect stay. We prepared breakfast every morning in our kitchen and ate on the screened-in porch and enjoyed some excellent restaurants in Orange for our lunches and suppers. Sleeping accommodations were very comfortable, bathrooms were roomy, and we even had the convenience of a washer/dryer combo. We were not aware that there was another house so close to ours, but, historically, it was lovely and was occupied by the owner's parents, which was very comforting having "good neighbors" close by. We were contacted by the owner to make sure everything went smoothly with our arrival and then we got a personal welcome from the owner a couple of days later. So kind! Our stay came to an end much too soon. We have stayed at VRBO rentals several times and this was by far the most comfortable and charming. We highly recommend it to all :-)

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

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

10/10 Excellent

R T.

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

Beautiful, historic cottage with amazing views

Perfect spot to unwind, relax and recharge. Close to things to do (wineries, shops, restaurants) but also feels wonderfully far away from the hustle and bustle. Comfy beds, fluffy towels, well appointed with modern amenities without losing any of the historic charm. Screened porch is wonderful for bird watching and listening to the cows from the distant dairy.
Stayed 4 nights in Nov 2024

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

10/10 Excellent

Lisa Lynn C.

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

Comfortable Calming Country Cottage

A simply elegant historical cottage with modern conveniences. Arriving at the property, I drove up a winding tree-lined drive past the main house and back to the cottage. It made me feel somewhat like I was in a Jane Austin novel. It had a perfect cottage look about it. There were beautiful english garden flowers and landscaping around the cottage. A convenient nice-size private parking area leads right to the entry door of the cottage. The large fireplaces were impressive architecture for the size of the cottage. The pastoral scene at the back of the property was breath taking. Wake up early, take a cup of tea or coffee to the screened-in porch, and quietly take in the vistas. It’s nature at its finest. A bird atop a large pyramidal holly would greet me every morning. Thank you God :). The owners/managers were extremely responsive per text; I had just a few simple questions. Unprompted, they left a large basket filled with extra towels and printed cards explaining the history of the property which was a nice touch. The history added to the interest of the cottage. I only used the downstairs area, and slept great. The bed was extremely comfortable and the shower was perfect. Overall the cottage had a very comfortable, quiet and calming affect. I felt extremely safe as a party of one. A great getaway for anyone who wants to escape a fast-paced world. Would definitely stay at this cottage again! Very grateful, thank you for sharing your home :)
Stayed 4 nights in Sep 2024

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

10/10 Excellent

Barb P.

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

Girls Trip 2024

We couldn't have asked for a more serene, peaceful and tranquil property to begin our trip. Your home brought us the reminiscences of days gone by and it captured our expectations of what we perceived our trip to be. The quaintness of your home was so welcoming and we hated to see our time there end.
Stayed 5 nights in Jul 2024

4/10 Poor

Robert B.

Liked: Cleanliness, check-in, communication, location

Just a few issues we had, but overall the place is nice.

Be careful not to lock yourself out onto the screened porch, as there is no door in the screened room where you can exit. Our main complaint is that there was no TV on the main level. Stairs are very steep, and we wanted to watch TV. We are in our early eighties, so this house was not ideal for us. Another issue we noted was that the main rooms are dark. There is no overhead lighting and there is not an abundance of lamps. The kitchen and bathrooms were very nice and brightly lit. For someone younger who is not especially interested in watching TV, this would be an okay choice. The yard, trees and flowers are beautiful. Again, the owner was very nice, but I'm just being honest about our experience which was impacted greatly by our ages.
Stayed 4 nights in Jun 2024

10/10 Excellent

Jessica M.

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

Absolutely Lovely

This property is lovely! The house, mantle, porch, view. We were serenaded by the evening sounds of bull frogs, deer and quiet! And they have more stars than you can imagine. Highly recommend!
Stayed 3 nights in Jul 2024

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

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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