Pet-friendly holiday rentals in Shelby County

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

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 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, fire pit 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.

Countryside On the Bourbon Trail, 22 Quiet Acres

Welcome to Sea Glass Farm. 1900's restored farmhouse with tons of charm! 22 acres of privacy. Cows may be present in pasture. The heart of The Bourbon Trail, the scenery and wildlife will not disappoint. The location is perfect for a rural getaway or relaxing stop on your Bourbon Trail experience. Minutes from shopping and restaurants; situated between I-64 and The Bluegrass Parkway. This place has been a dream of ours and we look forward to sharing it with you. Hosted by the owners.

EastwoodNest

Private 8-Acre Estate in the Heart of Eastwood City – 5 Bed | 5 Bath Experience the perfect blend of space, luxury, and urban convenience with this rare 8-acre private estate, nestled right in the heart of vibrant Eastwood City. Tucked away from the hustle, yet just minutes from top-tier shopping, dining, and entertainment. The expansive residence features 5 generously sized bedrooms and 5 full bathrooms, designed with comfort and functionality in mind. #HotRodShow, #StreetRodShow, #NSRA

*Distilleries close by* Hot tub*Firepit

Welcome to this beautiful, new 4 bedroom, 3.5 bathroom home ready to be the place for your bourbon trail stay! Centrally located just outside of Louisville. This home is less than 30 minutes from downtown Louisville where you can enjoy multiple distilleries, the Louisville Slugger Museum & Factory, Churchill Downs, the Fair & Expo, and just a short drive to Four Roses, Lexington and so much more! Air Hockey, hot tub, Golden Tee and fire pit are all waiting for your group to enjoy!

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.

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!

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

Bourbon & Bluegrass Retreat | Fun & Cozy Stay

Welcome to the Bourbon & Bluegrass Retreat — a fun, thoughtfully designed stay where modern comfort meets Kentucky charm. Each room is full of color, personality, and cozy touches made for relaxing and memory-making. Perfect for couples, friends, or families looking for something unique. Close to local favorites, outdoor adventures, and small-town charm. Come for the stay, leave with memories

Charming 4 Bedroom classic home bourbon trail!

Comfortable, newly furnished home located in downtown Simpsonville. This is brand new to AirBnB. Whether you are going down the Bourbon trail or you just want to be near I64 and Louisville, this home is the place for you. Fun, homey well decorated this place offers family fun with Fire pit, backyard and patio. High speed 300mb internet for those workers on the go.

Bourbon Trail, Hot Tub, Firepit, GameRm

Welcome to Magnolia Bourbon Manor, a beautifully restored historic home nestled in the heart of Kentucky’s bourbon country. Just three minutes from downtown Shelbyville, this charming property offers the perfect blend of vintage elegance and modern comfort, making it an ideal retreat for travelers seeking both relaxation and adventure.