Family-friendly holiday rentals in Shelby County

Ridgecrest Estate. Comfort and Convenience.

Enjoy the best of Kentucky in our immaculate, 650-sq-ft. upstairs studio apartment with private entrance on 5 acres in the heart of the Saddlebred Capital of the world. Just 9 miles east of the Watterson Expressway, Ridgecrest estate offers a quiet, peaceful environment in the heart of the Bourbon Trail. Quick access to I-64 (1/2 mile), 45 min. to Keeneland, 30 min to Churchill Downs, and 2 min to the Outlet Shoppes. Sleeps two. No children under 13. Pool access not included with reservation.

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.

Thoroughbred Horse Farm Cabin-located on Lamb Lake

Beautiful cabin located on a working horse farm just miles from Louisville, Frankfort and Lexington! Take in the farm scenery from our porch bed swing, or large patio with fire pit. Play a round of Air hockey, foosball, basketball shootout, corn hole, or bucket golf during your stay! Several Bourbon Distilleries are within a 30 minute drive of the property. The Cabin is 4 miles from the Outlet Shoppes of the Bluegrass, 15 miles from Taylorsville Lake, and 13 miles from Valhalla Golf Course.

4BR Farm~Bourbon Trail~private pool~horses

Sabre Hill Farm house rental is the perfect place to immerse yourself in the relaxing sounds of nature. On the 25 acres you will find all the comforts of home on a farm with horses, goats and mules. It is ideally positioned as home base for both indoor & outdoor activities including Derby & Horse Events, group gatherings &/or bourbon tours. Between activities unwind on the veranda or pool overlooking the horse paddocks. Saltwater Pool May thru Oct. heated 85*. Horse boarding available.

Close to all the popular distilleries Perfect Spot

Ultra Luxury downtown 2 BR loft, spacious enough for 5 adults. Located in quaint Downtown Shelbyville, KY, you are in the heart of the bluegrass near major distilleries and race tracks and close to coffee shops, restaurants and bars right on the same block. You can't go wrong with this unique loft for its decor and proximity to everything. Close to all distilleries on the eastern part of the Trail and centrally located to all distilleries in the state. Come see what this space has to offer

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.

Cabin with spectacular views, creek, & hot tub

Located on beautiful Brashears Creek in the heart of Bourbon Country, this loft style cedar cabin makes a great central location to visit some local distilleries and wineries. It is also a great place to stay for anyone who might be in the area for a horse show or interested in antique shopping along Shelbyville's historical Main Street. My personal favorite thing to do at the cabin is enjoy the creek. The water level fluctuates significantly depending on the amount of rainfall received.

The Bourbon Coop

The Bourbon Coop is arguably the best situated location on the Bourbon Trail! It is a convenient walk or golf cart ride to Whiskey Thief distillery across the street. Situated a quarter of a mile off interstate 64, in between Louisville and Lexington, with a 15 minute drive into the city of Frankfort. The cabin is located on a beautiful, scenic plot of land, shared by the friendly hosts, chickens, ducks and a couple of goats. This is a comfortable, quiet and quaint country experience!

Pleasureville - The name says it ALL

This location is a Pleasure! Cozy Kentucky home off the beaten path, but close to attractions. Imagine after a full day on the bourbon trail enjoying your own piece of Kentucky with a drink in your hand. Access to 25+ acres of beautiful farmland and super clean, fully stocked private home. Close to the Outlet Shoppes of the Bluegrass making it a perfect ladies weekend get away. Additional meeting/event space available in the renovated on site barn. Reminder No Pets allowed.

Cottage of Eden. Bourbon Trail Stay in Shelby Co.

Listen to the birds sing as the walkway guides you to your quaint cottage getaway. Take in nature, as you’re surrounded by trees, near our sweet chicken coop and a creek that flows down from the deck - all while only 10min from town. Special touches were added of Kentucky Derby photos, books, kitchenware, Bourbon Trail glasses and bourbon barrel heads with local distilleries. The dining table top is even made of wood from Shelby County’s own Bulleit Distilling Company.

Hidden View Cabin

Welcome to Hidden View Cabin, a delightful cabin where seeing wildlife and listening to the sounds of nature are yours to enjoy! Take the scenic drive down the gravel lane to this private and peaceful place located among pine trees and overlooking a one acre pond. Whether you have come to relax and get away from it all or want to visit the many attractions throughout central Kentucky this is the place for you. Only 20 minutes from Lawrenceburg.

Sip on bourbon in the hot tub! +hiking & game shed

A charmingly unique taste of KY waits for you at this peaceful log cabin! Perfect for those wanting to explore the 🥃Bourbon Trail🥃 or other nearby tourist attractions, While still featuring plentiful amenities on site, such as: - A hot tub - Private 1/4 mile hiking trail - Game shed - Fire pit - Covered porch - Wooded picnic area And more! Your next adventure is just a peaceful countryside drive away at the Kentucky Bourbon Den!