Pet-friendly holiday rentals in Shelby County

Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views

Welcome to your Bourbon Trail getaway in Waddy, KY- perfectly located near Lawrenceburg, Shelbyville, Frankfort, and Versailles with easy I-64 access. This charming 3-bedroom, 2-ba home features hardwood floors, a fully equipped kitchen, jacuzzi tub, high-speed Wi-Fi, and self check-in. Relax on the front porch rocking chairs, unwind on the new patio, or enjoy breathtaking sunsets. Ideal for families, couples, or remote workers seeking a peaceful Kentucky escape close to horse country. Book now!

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.

Charming suite in Bourbon Country

A great base for bourbon tours, the Derby, Louisville and Central KY attractions. Easy access to I-71, 25 minutes from downtown Louisville. 5 minutes from distillery, brewery, and botanical gardens in scenic Oldham County. A beautiful spot off the beaten path to relax and recharge. Private two bedroom basement suite with natural light, dedicated entrance, and privacy. Shared outside covered deck and yard with mature trees. 1 queen, 2 twin beds, 1 queen air mattress.

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!

2 Bed/2.5 Bath Restored Beauty - Pistachio Palace

Built 1904 and recently lovingly restored. Just 2 blocks off historical Main Street in Shelbyville with great antique and coffee shops, as well as some favorite pubs and restaurants. In the middle of the Bourbon trail and Horse country, short drive to the new Convention Center and the Outlet Mall. This neighborhood is in the midst of gentrification. 2 Queen Beds, one Roll-away, pack-n-play & high chair. Absolutely no pets, including service dogs.

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

Downtown House with Hot Tub and Speakeasy

Unwind in the hot tub under string lights, sip bourbon by the fire pit, and gather in your own private speakeasy—this downtown Shelbyville home is perfect for unforgettable group getaways just minutes from the Bourbon Trail. A beautifully restored historic home, it blends classic charm with modern comfort and offers plenty of space to relax, connect, and make lasting memories.