One of Central Virginia's most historic Private Guest Residences

Orange, Virginia
$314 avg/night Minimum Stay 2 Nights
Bed 2

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 6

Max Sleeps

Night 2 nights

Min Stay

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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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Smoke Detector Not Reported (host Has Not Indicated Whether There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 1000 Sq Ft (93 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Microwave Refrigerator Spices Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Car Recommended Limo/town Car Service Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Barbecue Grill Patio
  • BATHROOMS

    2 Bathrooms Hair Dryer Towels Provided
  • THINGS TO DO

    Birdwatching Nearby Fishing Nearby Horse Riding Nearby Hunting Nearby Mountain Biking Nearby Wildlife And Game Walks Nearby Winery Tours Nearby
  • ENTERTAINMENT

    DVD Player Smart TV With Cable/satellite Service
  • LIVING SPACES

    Fireplace
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Highchair Travel Crib
  • LOCATION HIGHLIGHTS

    Near A Health Or Beauty Spa
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Cobblestone Flooring In Public Areas If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 6

Map Map

School District Rates & Availability

Review Review

  • Stina Marie S.

    Submitted Dec 30, 2025

    Stayed Dec 26, 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.

  • David O.

    Submitted Oct 28, 2025

    Stayed Oct 26, 2025

    Everything was excellent! Enjoyed our stay very much! Would come again!

  • Suzanne D.

    Submitted Jul 13, 2025

    Stayed Jul 11, 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.

  • Mary M.

    Submitted Jun 30, 2025

    Stayed Jun 15, 2025

    Felt like we stepped back into history. Was lovely. And the quiet peaceful property was just what we needed.

  • Faerlie H.

    Submitted May 26, 2025

    Stayed Apr 24, 2025

    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!

  • Susan G.

    Submitted Apr 24, 2025

    Stayed Apr 21, 2025

    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.

  • Nancy R.

    Submitted Jan 21, 2025

    Stayed Jan 17, 2025

    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!

  • R T.

    Submitted Nov 21, 2024

    Stayed Nov 13, 2024

    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.

  • Elizabeth F.

    Submitted Nov 10, 2024

    Stayed Nov 7, 2024

    In beautiful farm surroundings

  • Lisa Lynn C.

    Submitted Sep 30, 2024

    Stayed Sep 16, 2024

    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 :)

  • Helen P.

    Submitted Sep 19, 2024

    Stayed Sep 5, 2024

    Beautiful property and home

  • Barb P.

    Submitted Aug 5, 2024

    Stayed Jul 30, 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.

  • Mary H.

    Submitted Jul 30, 2024

    Stayed Jul 26, 2024

    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.

  • Robert B.

    Submitted Jul 10, 2024

    Stayed Jun 20, 2024

    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.

  • Jessica M.

    Submitted Jul 4, 2024

    Stayed Jul 1, 2024

    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!

  • Andrew T.

    Submitted Jun 1, 2024

    Stayed May 28, 2024

    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!

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Total

Includes taxes and fees
$314+
View details