Pet-friendly holiday rentals in Shelby County

5.0 out of 5 average rating, 21 reviews

Home in Waddy

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.

An outdoor fire pit area is featured, surrounded by several adirondack chairs arranged on a gravel surface. String lights illuminate the space, creating a warm ambiance. In the background, the house is partially visible, with an inviting seating area under a canopy.

4.98 out of 5 average rating, 64 reviews

Bourbon Trail! Game Room Hot Tub Speakeasy FirePit

Gather your crew for an unforgettable stay in Kentucky bourbon country. Magnolia Bourbon Manor is a beautifully restored historic home that sleeps 10, featuring a private speakeasy, covered hot tub, fire pit, and pool-table game room. Just 3 minutes from downtown Shelbyville, 12 minutes from Jeptha Creed and Bulleit, and 35 minutes from Louisville, it’s the perfect home base for Bourbon Trail adventures, weekends with friends, family getaways, and celebrations. Proudly hosted by a Superhost and

The exterior of a single-story brick house is shown under a clear blue sky. A driveway leads to a two-car garage, and a landscaped front yard features green grass and shrubs. A large window above the entrance highlights the architectural design.

4.97 out of 5 average rating, 68 reviews

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!

4.96 out of 5 average rating, 28 reviews

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

Farm stay in Simpsonville

The farmhouse is set against a vibrant sunset, illuminating the sky with shades of orange and pink. The white two-story structure features a welcoming porch, surrounded by lush green grass and a rural landscape.

Farm House - near Bourbon Trail & Pet Friendly

Late 1800's farm house on a 155 acre working family farm located in the heart of the Bourbon Trail. It is a unique experience to stay on our farm where we raise non-GMO corn that goes into producing bourbons here in Kentucky. The farm is rural and private, but convenient to Louisville, distilleries and many other local attractions. We are located only 10 minutes from the Gene Snyder Freeway in Louisville and 10 minutes from the Outlet Shops of the Bluegrass and 15 minutes from Shelbyville.

4.89 out of 5 average rating, 102 reviews

4.96 out of 5 average rating, 246 reviews

A restored farmhouse is shown with a charming white exterior and a black roof. The front porch features white railings, while the surrounding lawn is well-maintained with a grassy area and some trees in the background.

Chalet in Lawrenceburg

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.

4.91 out of 5 average rating, 79 reviews

A hot tub filled with water sits invitingly, surrounded by greenery and a clear sky. A glass of whiskey rests on the edge, complementing the tranquil setting. The bubbles within the hot tub suggest relaxation awaits in this outdoor space.

Home in Simpsonville

*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!

5.0 out of 5 average rating, 32 reviews

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.

5.0 out of 5 average rating, 9 reviews

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.

4.87 out of 5 average rating, 31 reviews

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