Häuser als Ferienunterkünfte in Shelby County

Bourbon, Bridles & 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!

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.

Hot Tub Speakeasy Game Room FirePit Bourbon Trail

Gather your crew for an unforgettable bourbon-country escape. This restored historic home in downtown Shelbyville sleeps 10, with a private speakeasy, covered hot tub, fire pit, and pool-table game room — everything you need to celebrate under one roof. Just 3 min to downtown, ~12 to Jeptha Creed & Bulleit, 35 to Louisville. Superhost-hosted Guest Favorite, stocked to the last detail. Whether you're here for a bourbon tour, a weekend getaway with friends, or a family trip, the home is set up to

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

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

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.

Hitching Post on the Bourbon Trl

The Hitching Post on the Bourbon Trail – Spacious Shelbyville retreat near charming downtown & walkable to the famous Horse Show. Minutes from Louisville & centrally located to top distilleries. Enjoy a man cave with poker, darts, shuffleboard & big screen TV, plus a screened porch for coffee or bourbon. Kids will love the playhouse over a stream in a fenced yard. Located in a safe, scenic community in the Saddlebred Capital of the World—your perfect base for bourbon & horse country!

Lakefront Horse Farm | Sleeps 12 | Bourbon Trail

Experience Kentucky horse country from your own private lakefront retreat. Nestled on a working Thoroughbred farm and sleeping up to 12 guests, this spacious home is perfect for Bourbon Trail weekends, family gatherings, golf trips, and peaceful escapes in the Bluegrass. Conveniently located between Louisville, Lexington, and Frankfort. Relax on the porch bed swing, gather around the fire pit, or enjoy air hockey, foosball, cornhole, bucket golf, and a basketball shootout.

Jeptha Crest-Bourbon Trail, Hot Tub, Sauna, Dog OK

Jeptha Crest is a designer-built and thoughtfully decorated home, perfectly placed in the heart of the Bourbon Trail yet hidden among trees and nature views. Though centrally located, it feels like a private forest escape, offering rare privacy and calm. A spacious two-level deck, fire pit, hot tub, and sauna invite you outdoors, while inside, clean modern design blends seamlessly with warm, cozy comfort — a refined retreat created for slowing down and truly unwinding.

Quiet Downtown Maple Cottage Gem

Welcome to our charming Maple Cottage in the heart of a peaceful downtown neighborhood. This 3-bedroom, 1-bathroom home has undergone a complete remodel, ensuring a cozy and comfortable stay in Shelbyville. Whether you're here for a weekend getaway or an extended stay, this cottage offers all the amenities you need. The fully fenced backyard offers privacy and space for relaxation and smores over the fire pit. Your Shelbyville adventure begins here!

Bourbon Trail Retreat: Pool, Hot tub & Game Room

Welcome to The Shelby Stop where comfort & style awaits you! This 4 bedroom, 2.5 bath home offers space for everyone. 2 bedrooms are on the main floor; 1 of which is the luxury primary bedroom with en-suite bathroom. 1/2 bathroom just off the kitchen. The primary bedroom is a beautiful room with king size bed, luxury mattress, linens, large smart TV, sitting chair, & full size mirror. The attached en-suite bathroom is newly renovated in 2023

LUX Farmhouse | HotTub | Firepit | GameRm | 5 Acre

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!