Vacation rentals with a patio in Shelby County

4.98 out of 5 average rating, 145 reviews

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.

5 out of 5 average rating, 20 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!

4.91 out of 5 average rating, 64 reviews

100 Proof Hideaway

The 100 Proof Hideaway is the perfect Kentucky get away for you. Conveniently located in Shelby County Kentucky along the Bourbon Trail. The 100 Proof Hideaway is the perfect hideaway if you’re visiting bourbon country, attending a wedding at Silo Farms, or just wanting to enjoy the gorgeous Kentucky bluegrass. This spacious and serene hideaway is conveniently located centrally to Louisville and Lexington. The gorgeous farmhouse is within miles of Jeptha Creed Distillery and Taylorsville Lake.

Guest suite in Shelbyville

5 out of 5 average rating, 14 reviews

Bourbon trail, Bourbon& Beyond countryside suite

Welcome to Kentucky! We have the perfect newly renovated guest suite for visitors whether you are headed to our famous Kentucky Derby, Bourbon Trail tours, or more. You will have your private entrance, a comfortable living area, a fully stocked kitchenette, a full bath, one bedroom with a queen bed, and a living room with a large sectional couch and TV. WiFi is available, and we are a short drive to Frankfort, Louisville, and Bardstown. #distillerytours#bourbon #bourbontrail #derby#railfest

Farm stay in Simpsonville

4.87 out of 5 average rating, 71 reviews

Horse Farm 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

5 out of 5 average rating, 13 reviews

The Country Pleasure Farm

Welcome to our 50 acre countryside retreat, where rustic charm meets modern comfort. Our spacious 3-bed, 3-bath home offers a cozy living area, a fully equipped kitchen, and stunning views of the surrounding countryside. Conveniently located near town, the Bourbon Trail, Golf Courses, Race Tracks, and Gallrein Farms, it's the perfect getaway for relaxation and adventure. We're a working farm so expect to see tractors and harvesting taking place during your stay at this quaint and cozy farm!

Guest suite in Shelbyville

4.98 out of 5 average rating, 63 reviews

Spacious suite, country views, pool table, firepit

Escape to the tranquility of the countryside at Marshalls Creekside Haven. Our lower-level walkout guest suite, with own driveway and entrance, offers the perfect retreat, providing comfort and relaxation. Enjoy the warm glow of the fire pit or sway gently on the porch swing, taking in the breathtaking country views that surround you. Indoors enjoy a game of pool, darts or board games. Convenient to bourbon trail, wineries and quaint towns. Cell service is AT&T. Wi-Fi provided by Starlink.

4.93 out of 5 average rating, 14 reviews

Kentucky Bourbon Trail Farmhouse-Serene Views-Pool

Come enjoy this incredible modern farmhouse and serene views, all while only being less than 10 minutes from all of Shelbyville’s amenities. We have done our best to take comfort to the next level with our memory foam beds and top of the line linens, decor, & furnishings. Start your days enjoying our bean to cup coffee overlooking the sunset rocking on the front porch, the heated saltwater pool in the afternoon, and your nights by the fire pit in the backyard enjoying the beautiful views.

4.98 out of 5 average rating, 42 reviews

Farm stay in Shelbyville

Beautiful Farm Stay on the bourbon trail!

This memorable place is anything but ordinary. Enjoy the picturesque views from the farmhouse of the pastures. Watch as the sheep and horses graze. On the hour you can hear the sound of church bells. When the wind is right, the smell of mash from local distilleries wafts through the air. Make one of a kind memories on our beautiful farm. Included in your stay are fresh farm eggs (when available), enough coffee, creamer, sugar for the first morning, and 6 bottles of water and farm tour.

5 out of 5 average rating, 32 reviews

The Back 40 ~ Modern*Bourbon*Scenic*Private

The Back 40...where rural charm meets the modern amenities you expect. Overlooking the Jeptha Creek and situated in a serene Kentucky cattle pasture, this piece of country gold is your gateway to Kentucky's lauded Bourbon Trail and the Saddlebred Capital of the World. The Back 40 is perfect for Bourbon Trail adventurers, those seeking a little retail therapy, or folks simply aiming to escape to a slower pace of life for just a spell.

4.97 out of 5 average rating, 34 reviews

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.