Holiday rentals in Bradfordsville

One-Level Family Retreat | Game Room • King bed

Welcome to your Bourbon Trail stay -a cozy, welcoming home perfect for relaxing & enjoying everything Central Kentucky has to offer. This 3-bedroom home sleeps 6 & features a private heated & cooled game room just steps from the house—private bedrooms are perfect for spreading out & unwinding after a day out. Enjoy king & queen beds, cozy living spaces, & a coffee bar to start your mornings right. Perfect for visitors exploring the area, work stays, or spending time with loved ones nearby.

Shot Glass Tiny House, 3 miles to Maker’s Mark

🏆 Featured as one of “5 Unique Stays in Marion County, Kentucky”, January 30, 2026. This is glamping at its best! Stay under the stars at the Shot Glass Tiny House on wheels, tucked at the end of a quiet backroad on the bourbon trail just 3 miles from Maker’s Mark. Enjoy rustic comfort while observing wildlife through the large front picture window and surrounding windows. Explore the Bourbon Trail by day, then return to relax by the fire pit, gazing at the stars in this cozy nature retreat.

Marigold Manor: Eclectic Unit 3 Apartment

Welcome to Unit 3 of Marigold Manor! This apartment features 1 bedroom, 1 bathrooms, a kitchen/living combo, back patio seating, a shared space fire pit, laundry closet, and parking in the rear of the home. While this is a multi unit home, each space has a private entrance and locked interior doors. Whether your stay is short or long, you'll find plenty of amenities to make yourself comfortable. If you want to book the entire home, book each unit. You must climb stairs to access this unit.

Lawsons Landing

Lawson’s Landing – A Historic Farm Retreat on the Bourbon Trail Welcome to Lawsons Landing, a peaceful countryside escape in Springfield, KY. Built in the late 1970s by Corbett & Ola Lawson, this home embodies warmth, history, and farm life. Enjoy stunning views, modern comforts, and the charm of a working farm. 3BR | 2BA | Sleeps 6 – Cozy living room, full kitchen, Wi-Fi, outdoor gazebo. Experience the beauty, history, and hospitality of Lawsons Landing-we can’t wait to host you!

*NEW* Secluded Cabin On Private Lake

Woodland Acres is located in the Heart of Kentucky, with spectacular views all around, year-round! Come enjoy this piece of heaven right on the Bourbon Trail! This unique and spacious hideaway has breathtaking views and is situated just 7 minutes from downtown Lebanon, KY. Enjoy a private lake and fishing dock, take a hike through the vegetation that surrounds you, or enjoy a cup of coffee on the wraparound porch. Ideal for leisure seekers, nature lovers, and families alike!

Cozy Cabin on the Bourbon Trail

Our place is close to the Bourbon Trail. You’ll love our cabin because of the warm interior and amazing outdoor space. Our place is good for couples, solo adventurers, business travelers, and families. This cabin located in the country on our 100 acre farm, but you are 3 miles from restaurants, groceries, pharmacies and shops. The location is also central to the distilleries: 15mi to Maker's Mark, 35mi to Jim Beam, 50mi to Woodford Reserve, Lexington, and Louisville

A Heavenly Home

Serene ~ Peaceful ~ Private ~Modern. Centrally located in the heart of Bourbon Country. This home is an ideal setting to relax and enjoy spending time with friends or family. You will no doubt find this newly constructed home to be cozy, comfortable, and inviting! Enjoy the wonderful outdoor space in a quiet country setting with beautiful scenery and woods, comfortable seating, including a porch swing, a play area for children, and you may even see a deer or two!

Sunny Side Up

Sunny Side Up is situated on the second floor of the Sunny Side Saloon, a historic building with a rich past. Originally serving as a Union Army Commissary during the Civil War, it later transformed into a cherished local establishment known as the Sunny Side Saloon. Here, JH Kearns once sold his own pre-prohibition whisky, often packaged in ceramic jugs. Located in downtown Lebanon, in the heart of Kentucky, Sunny Side stands proudly on the historic Bourbon Trail.

Ticky's Cottage at Empire Estate

Visitors, children and pets are not allowed on the property at any time. Booked adult guests enjoy all the amenities, such as an inground pool (May-Labor Day, 8 a.m.-10 p.m.), 4 manicured acres to roam, volleyball/badminton court (8 a.m.-8 p.m.), fire pit/picnic area (8 a.m.-10 p.m.) next to a stream, horseshoes and more, all within 50 minutes of the major Bourbon Country distilleries. Amenities and lodging are for booked adult guests only.

New custom built treehouse

Reconnect with nature at this unforgettable escape. Green River Breeze is a new custom built 4 season treehouse. This space allows you to immerse yourself in nature while enjoying all modern amenities of home. Suspended among the trees you will fall asleep in the loft on a king size bed. You will find a fully equipped kitchen, private bathroom and small living area BUT the real beauty is the expansive deck and outdoor firepit.

Coffee with the Squirrels

New chalet only 5 minutes to city of Somerset and 5 minutes to Lake Cumberland! Cozy 1 king size bedroom with custom features throughout. Walk out on your master suite deck and have coffee with nature! Full size bathroom w custom tile. Back deck that overlooks woods and wildlife. Sometimes there is a neighbor who has a dog that barks a couple housss down, I’m sorry if it does, doesn’t happen often

Spirit on Main

Welcome to Spirit on Main, located in Lebanon, the heart of Kentucky. Located on Main Street, in the middle of all of the local activities, Spirit on Main is prime location for visiting your favorite bourbon spots! Whether you are in town for a couple’s getaway, trip with friends or on business, Spirit on Main will be your home away from home in the beautiful small town of Lebanon.