Vacation 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

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!

Private Farm studio apartment on the bourbon trail

Enjoy this conveniently located working farm after a day of hiking, visiting the local distillery's, fishing nearby Guist Lake or Keenland and Churchill downs. You can sit on the deck of the beautiful pond and enjoy the sunset or the moon, wonder the property and pet the horses, goats, dairy cows and calves. Enjoy the banter of the chickens wondering around, watch the milking of the dairy cows or the daily farm chores. Fresh milk and eggs available during your stay if desired. *no cleaning fee

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.

Country guest suite. Bourbon trail close by.

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

Family, Friends, Bourbon & Lakeview Home

This unique new home is located on Guist Creek Lake in Shelbyville, KY. Enjoy time spent with family and friends in our beautiful open kitchen, living / dining room floor plan. The master bedroom features a queen size bed, large closet space and a full bath. Guest Room/Office offers a private area with twin fold out convertible couch to bed. Enjoy the beautiful view of lake from our covered deck, or stroll to the back of the property and down the stairs to enjoy a shaded view of the lake.

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.

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.