About Bourbon Oak

Welcome to Bourbon Oak Properties, where history meets comfort in the heart of Bardstown, KY. As a proud Airbnb Superhost with 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.

At Bourbon Oak Properties, we offer four distinct accommodations, each steeped in history and charm:

• Smokehouse Cottage: Once a smokehouse in the 1800s, this property now offers a unique blend of historic architecture and modern amenities.
• The Loft: A spacious 2-bedroom, 2-bath apartment-style unit perfect for families or small groups.
• Hideaway 1: A cozy studio with a full kitchen, ideal for a quiet, intimate getaway.
• Hideaway 2: A comfortable 2-bedroom, 2.5-bath apartment that offers ample space for relaxation.

Our properties sit on land with a rich history dating back to the American Revolutionary War, and we are honored to share this legacy with our guests. Each stay with us is not just about lodging but an opportunity to connect with the spirit and tradition of Bardstown.

We are committed to continuing the legacy of our parents, ensuring that every guest feels the warmth and love that fills these walls. Whether you’re visiting to explore Bardstown’s bourbon heritage, experience its historic charm, or simply relax, we invite you to stay with us and enjoy the perfect blend of history, comfort, and Southern hospitality.