Family-friendly vacation rentals in Shelby County

Close to Buffalo Trace/Transpo available-Must See

Best place to stay on the Bourbon Trail FEATURED on HGTV! Swanky! Stunning! Spectacular! You'll be in a top-floor loft overlooking downtown Shelbyville and perfectly situated in the heart of the Bourbon Trail! Incredible place to stay for Derby, Keeneland, PGA or local weddings and events---if you can pry yourself away from here! We specialize in making your stay an over-the-top experience and are happy to arrange chauffeured transportation, private chef accommodations, and dinner reservations.

Indoor spaces · Kitchen · Check-in

Bourbon, Bridles & Birdies Retreat

We would LOVE to welcome you to Bourbon, Bridles & Birdies Retreat! Nestled in a quiet & peaceful neighborhood in the historic district of downtown Shelbyville, this FAMILY-FRIENDLY home offers unique dining experiences, seriously good shopping & the fairgrounds less than a mile walk away. Do you have plans in the big city?This thoughtfully laid out, detail-packed home will be your perfect retreat to relax! Please see "The Space" section for all the amazing attractions Shelbyville has to offer!

Family · Indoor spaces · Cleanliness

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.

Family · Indoor spaces · View

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.

Kitchen · Family · Heating

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.

Kitchen · Family · View

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.

Family · Indoor spaces · Location

Lakefront Horse Farm | Sleeps 12 | Bourbon Trail

Experience Kentucky horse country from your own private lakefront retreat. Nestled on a working Thoroughbred farm and sleeping up to 12 guests, this spacious home is perfect for Bourbon Trail weekends, family gatherings, golf trips, and peaceful escapes in the Bluegrass. Conveniently located between Louisville, Lexington, and Frankfort. Relax on the porch bed swing, gather around the fire pit, or enjoy air hockey, foosball, cornhole, bucket golf, and a basketball shootout.

Kitchen · Family · View

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.

Indoor spaces · Family · TV

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.

Family · Indoor spaces · View

LUX Farmhouse | HotTub | Firepit | GameRm | 5 Acre

Brand-new luxury farmhouse on 5 private acres in the heart of Kentucky bourbon country. This 4BR retreat sleeps 12 and is built for unforgettable group getaways, with a massive game room, full bar, pool table, shuffleboard, foosball, poker table, 85” TV, covered 6-person hot tub, huge firepit, outdoor games, and a fully stocked chef’s kitchen. Minutes from Buffalo Trace, Bulleit, and Jeptha Creed. Send us a message with any questions!

Indoor spaces · Kitchen · Hot tub

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!

Family · Indoor spaces · Nearby

Comfortable sleek home bourbon trail

Whether you are going to the racetrack, visiting the bourbon trail, going to a PGA event, or just enjoying the beauty of Kentucky this is a wonderful place to stay. New construction clean contemporary design, in the heart of the bluegrass. Close to Louisville, but located in the low crime feel good community of Simpsonville.

Indoor spaces · Family · Hospitality