Pet-friendly holiday rentals in Shelby County

Bourbon Trail Estate | Theater, Games & Hot Tub

✨ Escape to The Bourbon Barrel Retreat ✨ Designed for bourbon trail weekends, family gatherings, and group getaways, this modern 6-bedroom retreat sleeps 16 and is built for making memories. Relax in the hot tub after the distilleries, challenge friends in the game room, enjoy movie nights in the private theater, or gather around the firepit. Next door is a cozy farm with horses! Located just minutes from Kentucky's most popular distilleries. 🌟 BOOK YOUR STAY TODAY! 🌟 Please note: No weddings.

Bourbon Trail*Firepit*Hot Tub*Gameroom*Speakeasy

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

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!

Parris on Main St - Downtown, Bourbon and Derby!

Close to everything when you stay at this centrally-located place. Parris on Main Street is the perfect location to enjoy the historic town of Shelbyville, a few blocks walking distance to many antique shops, local coffee houses and great locations to grab a bite. Newly renovated, built in 1942, this house is perfect for a family or group of friends wanting to experience the wonderful places Kentucky has to offer. Right in the middle the Bourbon Trail and about 30 minutes from Churchill Downs

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.

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!

1909 BourbonTrail Gem | 4 King Beds | Fire Pit

Discover The Copper & Oak, a beautifully restored 1909 home in downtown Shelbyville. This spacious 4-bedroom, 4-bath property features two full living spaces connected by a speakeasy-style door, fully stocked kitchens, king bedrooms, and cozy gathering areas. Enjoy shuffleboard, the covered patio, and walkable access to shops, dining, and the Kentucky Bourbon Trail. Perfect for groups seeking comfort and charm.

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

Comfortable sleek home bourbon trail

Whether you are going to the racetrack, visiting the bourbon trail, going to a PGA event, or just enjoying the beauty of Kentucky this is a wonderful place to stay. New construction clean contemporary design, in the heart of the bluegrass. Close to Louisville, but located in the low crime feel good community of Simpsonville.