Pet-friendly holiday rentals in Anderson County

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 the Kentucky 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!

Barndominium on the Bourbon Trail - **HOT TUB**

Welcome to our farm! Enjoy 34 acres of rolling hills and woods with beautiful views of horses and wildlife. We are located 1 mile from the BG Parkway giving you easy access to all the FUN Kentucky has to offer. LOCATION: Within 10 miles of Four Roses, Wild Turkey, and LBC . Within 25 miles of Buffalo Trace, Keeneland Race Track, Lexington Airport, UK Hospital, Shaker Village, Woodford Reserve, and Rupp Arena. Bring your horses or ride one of ours! Stall and pasture rental available.

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.

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 .

Four Roses/ Wild Turkey/HOT TUB/3 acres

Welcome to Lawrenceburg, KY! You can't get any better of a location than this home! 3 mins to the Bluegrass Pkwy, not far from the most sought after bourbon distilleries, Lexington, Versailles, Bardstown, Shelbyville and just under an hour from Louisville! You'll love the super comfy queen beds, wood burning stove, fire pit, HOT TUB, and 3 acres of privacy on a hill. Enjoy this beautifully updated farmhouse right in bourbon and horse country!