House holiday rentals 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.

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!

The Ridge: 6BR • 100" TV • Hot Tub • Speakeasy

Cat Ridge Resort is a modern, professionally designed private retreat in the heart of Kentucky bourbon country, perfect for unforgettable group getaways. Explore iconic distilleries by day, then return to luxury amenities and warm Southern hospitality—from a private speakeasy and relaxing wellness spaces to games, a firepit, outdoor lounges, chipping green, and more. 🥃 5 top distilleries within 25 minutes ✈️ Conveniently located between LEX & SDF 📍 Shelbyville & Lawrenceburg w/in 25 minutes

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.

Luxury Manor 8BR 16 Beds HeatedPool~Sauna~ HotTubs

🏠 EMINENCE DOWNS 🏠—KY luxury reimagined for big groups! Step into our recognized estate, explore our unrivaled amenities, and get ready to book your ultimate Bluegrass getaway. 🥃 HIGHLIGHTS: 🏊 Heated Pool & 2 Hot Tubs 🚿 outdoor shower 🧖 Barrel sauna 🔥Fire pit 🛏️ no bunks 🍿Cinema 🎤Karaoke 🎮Poker , Arcade & PS5 lounge 💅 Glam Suite 🧺3 dishwashers, dual laundry, and Starlink The ultimate home base for Bourbon Trail tours, reunions & retreats.

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!

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!

Bourbon Country Farm Stay | 6BR | Updated 2026

Recently Updated 2026! Bring the whole family to this spacious retreat on 5 acres with plenty of room to relax and have fun. Enjoy a pond, swimming pool, fire pit, pool table, ping pong, and multiple gathering spaces—too much to list! The pool opens on Memorial Day. A private, lighted pickleball or basketball court with nearby access. Less than 5 minutes from town and local winery and bourbon distillery. Newly remodeled, updated wifi.