Welcome to Bourbon Oak Properties, where history meets comfort in the heart of Bardstown, KY. Six years of hosting experience, we specialize in providing exceptional stays for groups ranging from 2 to 18 guests.

Our journey began as a small family-owned operation, driven by a deep appreciation for the rich heritage of Kentucky Bourbon and the need for warm, welcoming accommodations in the “Bourbon Capital of the World.”

Our parents, Robert “Bobby” and Carol Simpson, recognized the growing demand for affordable, temporary housing as Kentucky Bourbon gained popularity. They lovingly restored and transformed historic properties to create unique, comfortable stays that provide a true “home away from home” experience. Bourbon Oak Smokehouse Cottage offers an opportunity to step back in history in the historic town of Bardstown. Located within easy walking distance of historic Bardstown and right in the midst of the Kentucky Bourbon Trail. Our Smokehouse Cottage sits on part of a 3,000 acre grant of land awarded to Colonel Samuel Bealmear following his service in the American Revolutionary War. The cottage was built in 1825 as a wedding gift from Colonel Bealmear when his oldest daughter, Ruth married Joseph Brown. Colonel Bealmear’s wedding gift also included 950 acres from his original 3,000 acres which became the Oaklawn Plantation. The Smokehouse Cottage received its name when it was converted to a “meat house” for the plantation. You can still see the pegs in the large beams of the Cottage.​ Guest will have full access to the entire home. This is a historic building where we have tried to add some modern conveniences to offer our guest an exceptional stay. A king size bed is located on the second floor and is accessed by a narrow stairway. Additional guest can sleep on the pull out couch sleeper. A fully functional kitchen leads to a fenced in back yard with a beautiful view. We offer a washer and dryer which come in handy for longer term stays. Relax on the back patio and watch the sunset. Please note the bathroom is on the first floor.