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 Ky Bourbon Trail HOT TUB

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!

3BR Luxe Bourbon Trail Retreat • Hot Tub & Sauna

Welcome to The Bourbon Exhale by Topaz Stays—your professionally-designed escape along Kentucky’s iconic Bourbon Trail. This peaceful country home blends rustic charm w/modern luxury, including a private hot tub, barrel sauna, speakeasy game room & cigar lounge. Located near Wild Turkey, Four Roses & more, it’s the perfect base for a distillery getaway. *Wild Turkey Distillery (11 miles) *Four Roses Distillery (13 miles) *Downtown Lawrenceburg (8 miles) *Rail Explorers (17 miles)

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.

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.

Bourbon Trail*HotTub*Dog friendly*3BR*4 beds

A centrally located 3 bed 2 bath updated house in a family friendly neighborhood with a hot tub near downtown Lawrenceburg! Less than 10 minutes to Wild Turkey and Four Roses. Dogs Allowed! This rental has everything you need and proximity to Keeneland, multiple Bourbon Trail distilleries, UK athletics, Lexington and Frankfort! It is the perfect location for couples or families (and their 4-legged friends) looking to spend some time enjoying bourbon, horse racing, and all things Kentucky.

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 .