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Bourbon Trail: Caboose on the Farm

Nestled under the shadows of elm trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunk-beds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

Bourbon Barrel Cottages #2 on Ky. Bourbon Trail

Leave the Cleaning to Us – Your Bourbon Country Escape Awaits! Kick back, relax, and unwind in a stylish, serene retreat nestled in the heart of Kentucky’s Bourbon Country. Welcome to Bourbon Barrel Cottages, where nature, comfort, and convenience come together. Each of our five private two-bedroom cottages sits on its own two-acre lot, surrounded by wildlife and natural beauty—perfect for couples, friends traveling together, or anyone seeking peace and privacy. You'll Love Staying with Us!

"The Homestead" UPSCALE STAY - Downtown with Yard

This newly renovated home is stylish and centrally located. Situated in the heart of Downtown Lawrenceburg, just minutes from local shops, the county park, and a short drive to several Bourbon Distilleries! This home is great for groups and families looking to get away- with 3 beds and a pull out couch to accommodate your party's size. Upon entry you'll find a fully stocked kitchen with a large island for meal prep, a charming living room with Smart TV tech, and a fire pit out back. Cheers!

Countryside On the Bourbon Trail, 22 Quiet Acres

Welcome to Sea Glass Farm. 1900's restored farmhouse with tons of charm! 22 acres of privacy. Cows may be present in pasture. The heart of The Bourbon Trail, the scenery and wildlife will not disappoint. The location is perfect for a rural getaway or relaxing stop on your Bourbon Trail experience. Minutes from shopping and restaurants; situated between I-64 and The Bluegrass Parkway. This place has been a dream of ours and we look forward to sharing it with you. Hosted by the owners.

Tucked Away Treehouse- on the KY Bourbon Trail

Tucked Away Treehouse is located in Rooted Escapes, a small, tree-filled property filled with opportunities for rest, relaxation, and the great outdoors. Tucked Away Treehouse boasts a full-service kitchen, loft with memory foam queen bed (accessible only by ladder), a full bathroom, and pull-out couch (on the main level). One of our very favorite features is the full glass garage door which creates a fun, indoor-outdoor environment. We are certain you will love sleeping amongst the trees!

Sweet Hollow Farm

Sweet Hollow Farm is located near Taylorsville Lake. 30 miles from Louisville, 40 miles from Lexington and 25 from Bardstown. We have a small farm with a studio barn apartment. Private entrance with full bath. We also have a beautiful pool that we share with our guests. There is a horseshoe pit, fire pit and multiple outdoor seating areas. Kids and dogs welcome. We even have space for horses and boats. We can offer peace and quiet, a clear view of the stars and hummingbird theatrics.

Bourbon Crossing II

Welcome to your home away from home on the famous Bourbon Trail! Minutes from distilleries, wineries, and outdoor adventures. A spacious bedroom with a king-sized bed, luxury linens, and TV. Modern bath with a walk-in shower, plush towels, and complimentary toiletries. Full Kitchen is stocked with everything you need. Relax in the cozy living room with a smart TV and high-speed Wi-Fi. Enjoy an evening outside next to the wood burning fire pit with supplied firewood.

Greenwood Farm log cabin-pet friendly

It is a 200 year old log cabin in Woodford County on a cattle farm owned by the same family since the late 1700’s. It is located just 3.7 miles from the Kentucky Bourbon Trail, with 5 distilleries within 10 miles. It is a 20 minute drive to Keeneland Racetrack and the Bluegrass airport, 35 minutes to the Kentucky Horse Park and 1 hour to Churchill Downs. Another option is to spend time at the cabin enjoying the farm by either just sitting on the porch or walking.

Handcrafted Rustic Cabin on the Bourbon Trail

The cabin has been entirely built by the owner, Doris, (with help from family and friends) from reclaimed and local salvaged materials. Located on a beautiful Kentucky Scenic byway, on a working farm, the cabin is only 15 minutes from Wild Turkey Distillery, the town of Versailles , golf courses, dining, shopping, wineries and other major distilleries. 35 minutes from Keeneland race course, downtown Lexington, UK, Rupp Arena, the Horse Park and more .