Holiday rentals in Shelby County

Close to Buffalo Trace/Transpo available-Must See

Best place to stay on the Bourbon Trail FEATURED on HGTV! Swanky! Stunning! Spectacular! You'll be in a top-floor loft overlooking downtown Shelbyville and perfectly situated in the heart of the Bourbon Trail! Incredible place to stay for Derby, Keeneland, PGA or local weddings and events---if you can pry yourself away from here! We specialize in making your stay an over-the-top experience and are happy to arrange chauffeured transportation, private chef accommodations, and dinner reservations.

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!

6 Private Acres! HotTub/Theater | Gamerm | Arcade

Minutes from Kentucky’s iconic bourbon distilleries, Oak & Mash is a private six-acre log cabin retreat made for memorable group getaways. Relax in the covered hot tub, enjoy the home theater and bourbon lounge, or challenge your crew to pool, shuffleboard, arcade games, and a private 4-hole disc golf course. End the day gathered around the fire pit under the stars. With indoor and outdoor entertainment for every season, Oak & Mash is the perfect home base for your Kentucky Bourbon Trail getaway

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

The Rec Farm-Log Cabin, Private Lake & Arcade

Previously one of Shelbyville’s favorite with 4.95 rating and 80+ reviews — now refreshed under new ownership, same great experience! The Rec Farm—a private 13 acre pet friendly retreat with a renovated log cabin, serene lake views, hot tub, campsite and game-packed Rec Barn featuring ping pong, ski ball, and more. This hidden retreat combines rustic charm and modern comfort just minutes from I-64. Perfect for families, friends, and bourbon explorers looking to relax, reconnect, and unwind.

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.

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.

Annola Farm Guest House

Stay and be delighted with this newly renovated two-story guest house which adjoins our 11-stall horse barn. Framed by covered porches and shade trees, our guest house is a wonderful place to unwind and relax during your stay in beautiful central Kentucky. The best of both worlds--a lovely rural setting situated only minutes from the interstate, making travel to Churchill Downs, Valhalla Golf Course, and other attractions in nearby Louisville and Frankfort a breeze.

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.

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.

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.