House holiday rentals in Shelby County

5 out of 5 average rating, 10 reviews

Bourbon, Bridles and 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!

The exterior of The BarrelWoods showcases a modern farmhouse design with white board-and-batten siding and black trim. Large windows invite natural light, while decorative shutters add character. The lush green lawn is complemented by landscaping, creating a welcoming atmosphere against a clear blue sky.

5 out of 5 average rating, 72 reviews

Bourbon Trail*Hot Tub*Sauna*Mini Golf*Wi-Fi*EVSE

Welcome to The BarrelWoods, the perfect retreat in the heart of the Bourbon Trail. This newly built home blends modern luxury with rustic charm, featuring designer touches throughout.Relax by the outdoor firepit, soak in the hot tub, or rejuvenate in the barrel sauna.Enjoy mini golf, archery, disc golf, and a game room with air hockey, shuffleboard, and more.Ideally located near iconic distilleries, fine dining, and scenic parks, The BarrelWoods is the ultimate base for an unforgettable getaway.

4.97 out of 5 average rating, 177 reviews

The exterior of a modern cottage is displayed, featuring a gray wood-paneled facade, a sloped roof, and a welcoming front entrance. A wooden staircase leads up to the porch, where inviting seating arrangements can be seen. Lush greenery surrounds the home, enhancing the tranquil setting.

Home in Lawrenceburg

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.

The exterior of a single-story brick house is shown under a clear blue sky. A driveway leads to a two-car garage, and a landscaped front yard features green grass and shrubs. A large window above the entrance highlights the architectural design.

4.96 out of 5 average rating, 53 reviews

Bourbon Trail*4BR*Dog Friendly*6beds (3king)*Patio

A great centrally located 4 BR 2.5 Bath (6 beds) dog-friendly house near downtown Shelbyville! Located in a cul-de-sac on a quiet street in a family friendly neighborhood 6 miles from Bulleit Bourbon, 3 miles to Jeptha Creed Distillery, and 1 mile from the Shelbyville Horse Show. Fully updated & stocked, coffee pot (K-cups or ground), washer/dryer, & 5 smart TVs. This rental has everything you need and proximity to Churchill Downs, multiple Bourbon Trail distilleries, Louisville, and Frankfort!

A charming single-level home is presented with a welcoming front porch featuring rocking chairs. Lush grass and neat landscaping frame the stone pathway leading to the front door. Trees provide shade, creating a serene setting in a quiet neighborhood.

5 out of 5 average rating, 59 reviews

Brown Ave Bourbon Trail & Beds- Shelbyville, KY

Welcome to Brown Avenue Bourbon and Beds, a beautifully renovated 1950's charmer on the Bourbon Trail, near the Shelby County Fairgrounds & just minutes from downtown Shelbyville. Start your day w/ coffee on the front porch swing, enjoy an afternoon snack on the back deck, cook dinner in the fully stocked kitchen & cozy up in the living room for movie night after a long day of exploring! A short drive to Louisville, Lexington, Frankfort, KY Derby and PGA Championship 2024 @ Valhalla! Sleeps 6

4.92 out of 5 average rating, 130 reviews

Home in Finchville

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.

5 out of 5 average rating, 22 reviews

A light-filled living area features warm wood flooring and a decorative area rug. A cozy seating arrangement is centered around a coffee table, with a fireplace made of exposed brick as a focal point. Natural light streams through the windows, illuminating the inviting space.

Home in Pleasureville

Bourbon Trail Country Getaway

Escape to the peaceful countryside and unwind in our restored farmhouse surrounded by rolling farmland. This secluded retreat with three gas fireplaces is ideal for romantic getaways, bourbon enthusiasts, or family-friendly stays. Whether you’re sipping morning coffee on the porch, gathering around the firepit, enjoying some friendly competition in the game barn, or exploring the nearby Bulleit Bourbon Distillery on the Bourbon Trail, you’ll find tranquility and adventure in equal measure.

5 out of 5 average rating, 26 reviews

A charming outdoor area features a multi-level deck with a bright umbrella over a seating area. Red Adirondack chairs are surrounded by lush greenery and flowering plants. A gazebo with string lights offers a cozy space for relaxation, while a pathway connects various sections of the garden.

Home in Louisville

Red Bridge Retreat

Red Bridge Retreat is your perfect Christmas getaway! Set on 5 serene acres just outside Louisville, you’re only 30 minutes from major holiday events. Elegant, stylish décor throughout. This 4-bed, 3-bath private home features a kitchen deck with a Blackstone & gas grill, a covered patio with HOT TUB, a covered fire-pit area, a fully equipped kitchen, a game room with bumper pool & Pac-Man, and a tree-lined drive. It even includes a bourbon-themed lounge to unwind and relax.

4.98 out of 5 average rating, 150 reviews

Home in Bagdad

Lux Farmhouse | HotTub | Firepit | GameRm |5 acres

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!

4.93 out of 5 average rating, 80 reviews

Bourbon Country Farm Stay | 6BR | Updated 2026

Recently Updated 2026! Bring the whole family to this spacious retreat on 5 acres with plenty of room to relax and have fun. Enjoy a pond, swimming pool, fire pit, pool table, ping pong, and multiple gathering spaces—too much to list! The pool opens on Memorial Day. A private, lighted pickleball or basketball court with nearby access. Less than 5 minutes from town and local winery and bourbon distillery. Newly remodeled, updated wifi.

5 out of 5 average rating, 33 reviews

The cabin's exterior is shown at dusk, featuring a striking A-frame design with large windows and a dark roof. Warm lights illuminate the wraparound porch, enhancing the architectural details. The surrounding grassy area slopes gently, with a gravel drive leading up to the entrance.

Home in Waddy

Private A-frame Cabin | Hot tub, Firepit & Views

Welcome to Peletah Escape — our family’s cherished retreat nestled in Kentucky’s rolling hills. This cozy cabin offers sweeping views, a wraparound porch, hot tub, fire pit, game room, and plenty of space to relax. Inside, you’ll find rustic charm with modern comforts, from a fully stocked kitchen to comfy beds and a bourbon bar. Whether you're here to unwind or explore, Peletah Escape is your perfect Bluegrass getaway.

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