House holiday rentals in Anderson County

Cottage On Crooked Creek

A tranquil cottage nestled in the lush countryside and situated right along the Bourbon Trail, this completely renovated rare find is located center of Lawrenceburg, Frankfort and Shelbyville and only 12 min to I-64. With five main bourbon distilleries just 30 min, local wineries within a stone's throw, Churchill Downs and Keeneland Racecourse equidistant and Taylorsville Lake nearby there is little left to be desired when staying here. This is the perfect spot to relax with family and friends.

Birdsong Valley on Bourbon Trail

Great central location on Bourbon Trail. Close to Lexington, airport, Keeneland, Ride the Rails, Horse Park, Shakertown, many other attractions. You will love our 3 bedroom charming home on 2.2 beautiful acres in peaceful community. Perfect for couples, friends, families, singles to explore distilleries, horse farms, quaint small towns of Versailles, Midway, Lawrenceburg, country backroads, much more. OR relax, enjoy nature, butterflies, birds, deer. Let us make lodging highlight of your visit.

Peaceful Lake House Fire Pit Canoe Fishing

Lakefront 2 bedroom, 1 bath Home on Beaver Lake, located on the Bourbon Trail. Enjoy quiet surroundings as you sit on the back porch overlooking a cove of the lake. Spend the day fishing in one of our Angler's Kayaks or Canoe, head out on the Bourbon Trail, visit a nearby Winery, or cheer on the races at Keeneland. Enjoy your evening tucked away at the back of Beaver Lake with an outdoor firepit for s'mores and an indoor faux fireplace for ambience. Peace & privacy, yet only miles from town.

"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!

Bourbon Trail! Tavern*Hot Tub * EV Charger

Welcome to The Tavern on the Trail, a beautifully restored 1800's home located in the heart of Lawrenceburg, Kentucky, centrally located along the Bourbon Trail. This home was once a tavern for the area in the 1800's. The tavern is a perfect blend of historic charm and modern amenities, ideal for bourbon lovers, horse enthusiasts, and those looking to experience a true slice of Kentucky history. Guests will love being centrally located to the popular distilleries along the Bourbon Trail!

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.

Lakefront. Boat Dock. Private Bar. Hot Tub

Escape to a unique lakefront retreat with a personal dock, perfect for relaxation and recreation. Enjoy the serene setting with a private firepit, BBQ, and pizza oven for cozy nights in. The charming horse jockey theme adds character to every room, creating an inviting atmosphere. Whether you're unwinding by the water, savoring a homemade pizza, or enjoying a drink at the bar, this getaway offers a memorable experience in a one-of-a-kind setting. Ideal for couples or small groups.

Comfort in the Bluegrass

Comfort in the Bluegrass is a very clean, home nestled in the heart of bourbon and horse country. If it’s a little R&R you’re after, or entertainment…. This is the perfect location for either! We sit in a beautiful 1.6 acres located in a quiet, peaceful area in Anderson county. You can choose to relax with your friends or family by the fire pit, or tour one (or several) of the many sites around here! We are in between Lexington and Louisville, and only a few miles from Frankfort.

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.