Holiday rentals with a pool in Shelby County

MacAttie Acres

Country home at MacAttie Acres in central Kentucky is conveniently located on the Bourbon Trail and in the middle of horse country. Located only 2 miles south of Exit 48 on I-64. Relax on the deck and enjoy the view of the farm, the horses grazing in the pasture or take a hike to the creek. 10 miles to Wild Turkey Distillery, 12 miles to Four Roses Distillery, 13 miles to Buffalo Trace, 29 miles to Keeneland, 48 miles to Churchill Downs, Stabling and turnout available for horses. Come visit!

Private Estate on Bourbon Trail : KY Derby : Pool

Welcome! Bring the whole family to Horse & Bourbon Country with plenty of room for fun. Enjoy a day at any of the local Distilleries with Bulleit, Wild Turkey, Buffalo Trace and many more within a 25 minute drive and then come back to a relaxing sunset on a spacious back deck with a view of the pool, hot tub and fully stocked 1 acre pond. You can enjoy a night of Billiards, Shuffleboard or a movie inside the Theatre room. Situated between Churchill and Keeneland there is something for everyone!

*New* sauna+hot tub+pool+game room+speakeasy

Escape to comfort and style at Expression on the Rocks: A newly renovated 6BR, 4,400 sq ft retreat in the heart of the Bourbon Trail. Set on 5 lush acres with scenic views of hills and wildlife, this home offers a heated pool, hot tub, sauna, speakeasy with poker lounge, and a fully equipped gameroom. Perfect for group getaways-just minutes from Kentucky’s world-famous distilleries. Who needs to be the center of the universe when you can stay in the center of the Bourbon Trail? Book Now!

B on the Bourbon Trail with pub, pool and hot tub

Discover Kentucky's Finest - B on the Bourbon Trail. With a saltwater pool, hot tub, fire pit, and Pub B, this historic colonial estate on 3 acres is near over 30 renowned distilleries, 35 minutes from the iconic Churchill Downs, and just an hour away from the prestigious Keeneland racecourse, B On The Bourbon Trail offers unparalleled access to Kentucky's most treasured attractions and promises an unforgettable experience in the heart of Kentucky's bourbon country.

Bourbon trail luxury 4 bdrm getaway!

This stunning luxury home is perfect for any occasion! Located just 15 minutes from downtown Louisville/Churchill Downs. Large living room, games room will provide you with all the comforts and space for you and your friends/family needs. You can spend your time relaxing in the pool (summer only), sitting by a fire, catching a game on the outdoor deck, BBQing, sitting at the bar or playing games. Pool is open April 26 to September 5 for the 2024 season.

Bourbon Trail*Hot Tub*Game Rm*Pool

Welcome to The Shelby Stop where comfort & style awaits you! This 4 bedroom, 2.5 bath home offers space for everyone. 2 bedrooms are on the main floor; 1 of which is the luxury primary bedroom with en-suite bathroom. 1/2 bathroom just off the kitchen. The primary bedroom is a beautiful room with king size bed, luxury mattress, linens, large smart TV, sitting chair, & full size mirror. The attached en-suite bathroom is newly renovated in 2023

Hot Tub, 10 min to Bulleit

Escape to our serene haven nestled in the heart of the Kentucky Bourbon Trail. This inviting property offers the perfect home base for your bourbon tasting adventures. The Bourbon Bungalow is located in a rural/residential area across the street from Guist Creek Lake in the charming town of Shelbyville. We are midway between Louisville and Lexington and perfectly situated for visits to a plethora of distilleries.

Countryside Getaway

Welcome to your rural oasis! At our ranch you will experience your full country getaway. Enjoy the rolling hills of the Kentucky Bluegrass from the beautiful and secluded town of Fisherville. Just a 10 minute drive from major highways leading to downtown Louisville, our barn apartment is the perfect balance between getaway and easy access to everything the city offers.

Cozy Cottage on Firefly Farm

Carriage House Garage with breathtaking views of Firefly Farm. Conveniently located in Bourbon Country just thirty minutes away from Louisville or Frankfort. Enjoy meet and greets with our donkey and her flock of sheep, beautiful sunrises and sunsets from the comfort of your own private porch, and so much more.