Holiday rentals with a patio in Shelby 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.

Historic Downtown~Heart of Bourbon Trail

The Washington Belle is an historic home, freshly renovated with all the modern conveniences, centrally located in Shelbyville, Kentucky. She's the perfect base from which to explore the distilleries of the Bourbon Trail, with easy access to Louisville and Lexington. There are multiple restaurants, cafes, bourbon bars and antique stores in easy walking distance. Boasting two large living areas, three large bedrooms (including a master with ensuite), 2.5 baths, and private off street parking

Spacious Home with Beautiful Views

Very private house to yourself with acres to enjoy the beautiful outdoors. Cute downtown Simpsonville with restaurants and shopping only 3 miles away. Full kitchen with all basic items, Keurig and drip coffee pot, outdoor gas grill. Large living room with views of the horse pasture. Sunroom with large windows with wooded view, excellent room to watch the sunset behind the trees. Horses next door and in front. Fire pit in backyard. NO PETS. No longer accepting 1 night stays - 2 night minimum

Cozy Kentucky Winter, Bourbon Trail, Location!

♡ Meet The Blue Belle: a beautifully restored 1880s cottage ON the Bourbon Trail, nestled on a peaceful block in the heart of Shelbyville. Start your day with a coffee on the back deck, make s'mores by the fire pit, cook dinner in the fully stocked kitchen, & cozy up in the living room for movie night after a long day of exploring & bourbon! A short drive to Louisville, Lexington, & Frankfort and other great areas. Comfortably sleeps 8. Perfect for families & couples!

Bricks and Barrels

Quiet studio apartment in a historic home in downtown Shelbyville. It is within walking distance of downtown shopping, wedding venues (The Gatsby and Avonley Homestead) and dining on Main Street. First floor accommodations with a private entrance and also a private door to the back garden area. Centrally located between Churchill Downs in Louisville and Keeneland Race Course in Lexington. A perfect place for your stay along the Bourbon Trail or a weekend of antiquing.

Charming Bourbon Country Retreat on Beautiful Farm

The Horse & Hound is a unique and charming home located on Chickapoo Farm. This 100+ year old farmhouse is the perfect place to come relax, unwind, and get away from the hustle and bustle of city life. The elegant and captivating features in this historical home, along with the beautiful landscape are sure to make your stay a memorable experience. Fall back to a simpler time and feel the stress melt away at Chickapoo Farm in Shelbyville, KY.

Pool is Open! + 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.

Pool*HOT TUB*Bourbon Trail

Are you looking for location? Look no further! This stunning home has everything your group could want! Centrally located with easy access to Louisville, Frankfort, Lexington, & so much more! In the summer the pool will be refreshing & all year long the hot tub will serve as a treat after a long day exploring! Let's not forget about the incredible game room with shuffleboard and pool table!

Country Retreat on Bourbon Trail - Fire Pit - King

Surrounded by farmland, but close to Louisville, Frankfort, distilleries, and shopping! Start your morning on the front porch with a cup of coffee or tea and watch the horses across the way. Hop over to Louisville for the day, and afterwards, your tranquil country oasis awaits! Grill out and chill by the fire pit. Do some star gazing. Or just enjoy the peace of Kentucky’s countryside.