Vacation rentals in Shelby County

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

Comfortable Charm on the Bourbon Trail

You’ll be charmed by this adorable place to stay, close to the interstate, making travel to Valhalla Golf Course, bourbon distilleries, Churchill Downs, and other attractions in nearby Louisville a breeze. We are in a beautiful rural setting, just right for relaxing. Our space has its own private entrance with a comfortable living room and private bathroom downstairs, and features a loft with queen bed and desk. There are a microwave, coffee maker, and fridge available for your convenience.

Kentucky bourbon, horses, cozy condo

Welcome to your home away from home! Great place to stay while visiting local establishments, horse shows, bourbon trail, extended work stay or family. Work or Play this adorable condo was recently renovated and has all the comforts of home! King bed in main bedroom with full bath, queen size guest bed and 2nd large bathroom, wifi, fully furnished kitchen along with washer and dryer. Parking at your entrance with no steps! Just minutes from I64, groceries, restaurants and shopping!

The Haven Simpsonville* Bourbon Trail* 3 bed/3bath

Welcome to the Haven in the heart of Simpsonville, KY, the Saddlebred capital of the world. Located within walking distant of local eateries, shopping, & coffee. The Haven is close to local Distilleries, centrally located between Louisville and Lexington, on the Bourbon Trail, and less than 2 miles from The Outlet Shoppes of the Bluegrass. This spacious 3 bedroom, 3 bath home was designed to be a place of peace & comfort and is perfect for both families and group trips alike.

Cottage of Eden. Bourbon Trail Stay in Shelby Co.

Listen to the birds sing as the walkway guides you to your quaint cottage getaway. Take in nature, as you’re surrounded by trees, near our sweet chicken coop and a creek that flows down from the deck - all while only 10min from town. Special touches were added of Kentucky Derby photos, books, kitchenware, Bourbon Trail glasses and bourbon barrel heads with local distilleries. The dining table top is even made of wood from Shelby County’s own Bulleit Distilling Company.

The Lucky Penny Downtown Loft - Central Location!

Experience timeless charm in this beautifully renovated mid-19th century Airbnb in the heart of Shelbyville. With soaring 14 ft ceilings, this historic gem combines classic architecture with modern amenities. Centrally located, it offers convenient access to local attractions, dining, and shopping. Enjoy a blend of elegance and comfort in a space that honors its rich heritage while providing all the contemporary conveniences you need for a memorable stay.

Hidden View Cabin

Welcome to Hidden View Cabin, a delightful cabin where seeing wildlife and listening to the sounds of nature are yours to enjoy! Take the scenic drive down the gravel lane to this private and peaceful place located among pine trees and overlooking a one acre pond. Whether you have come to relax and get away from it all or want to visit the many attractions throughout central Kentucky this is the place for you. Only 20 minutes from Lawrenceburg.

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.

Ideal Location + Futuristic Decor | Galaxy Getaway

Welcome to Galaxy Getaway! This cosmic-themed studio on 6th Street in Shelbyville, KY, offers unique, out-of-this-world amenities for an unforgettable getaway. Whether you’re here to relax or embark on an adventure, your galactic escape starts here! 📍Prime Location 👾 Variety of fun games 🚀 Out of this world decor ✨ Modern amenities