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

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

Cozy Lakeview Home, family, friends, bourbon trail

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.

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!

The Back 40 ~ Modern*Scenic*Private*EV Charger

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.

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.

Bourbon Trail Getaway~Hot Tub, Pets OK, Game Room

✨Welcome to Bourbon Barrel Escape — your perfect launch pad for exploring Kentucky’s legendary Bourbon Trail! Located in charming Shelbyville, our stylish, fully furnished home is minutes from two local distilleries and less than an hour from 30+ more. Whether you’re sipping bourbon, soaking in the hot tub, or playing a game of pool, this retreat has everything you need for a fun and relaxing getaway