Pet-friendly vacation rentals in Shelby County

The exterior of The BarrelWoods showcases a modern farmhouse design with white board-and-batten siding and black trim. Large windows invite natural light, while decorative shutters add character. The lush green lawn is complemented by landscaping, creating a welcoming atmosphere against a clear blue sky.

5 out of 5 average rating, 57 reviews

Bourbon Trail*Hot Tub*Sauna*Mini Golf*Wi-Fi*EVSE

Welcome to The BarrelWoods, the perfect retreat in the heart of the Bourbon Trail. This newly built home blends modern luxury with rustic charm, featuring designer touches throughout.Relax by the outdoor firepit, soak in the hot tub, or rejuvenate in the barrel sauna.Enjoy mini golf, archery, disc golf, and a game room with air hockey, shuffleboard, and more.Ideally located near iconic distilleries, fine dining, and scenic parks, The BarrelWoods is the ultimate base for an unforgettable getaway.

An inviting historic home with a vibrant blue exterior is showcased against a clear sky. The front door, adorned with multiple panes of glass, complements the white trim and large windows. Lush greenery surrounds the entrance, enhancing the charm of this property.

5 out of 5 average rating, 54 reviews

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

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.

4.98 out of 5 average rating, 42 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!

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.

4.88 out of 5 average rating, 80 reviews

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.

4.96 out of 5 average rating, 228 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.

4.94 out of 5 average rating, 53 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!

Superhost

The spacious living room features large circular windows that provide ample natural light. Two comfortable sofas, one in a warm rust color and another in dark upholstery, are arranged around a decorative coffee table. An elegant area rug enhances the warmth, while indoor plants add a touch of greenery.

4.92 out of 5 average rating, 79 reviews

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!

4.95 out of 5 average rating, 60 reviews

A modern farmhouse is depicted, showcasing a wraparound porch with rocking chairs. Lush greenery surrounds the property, which rests on a spacious lawn. The sky displays a gradient of vibrant colors during sunset, enhancing the peaceful setting.

Home in Frankfort

4BR Retreat•Hot tub•FirePit•Near Buffalo Trace

Bourbon Hills Retreat is a newly renovated 4BR, 2.5BA farmhouse on 13 private acres with stunning hilltop views. View the hollers of KY. Sleeps 8 comfortably. Enjoy the hot tub, porch rocking chairs, starry nights, and peaceful surroundings. Minutes from Buffalo Trace & Bulleit, horse tracks, wineries, and Bourbon Trail favorites. Centrally located between Louisville & Lexington—perfect for family getaways, couples, or group trips exploring Kentucky’s best!

4.85 out of 5 average rating, 185 reviews

A charming home is shown with a light-colored exterior, framed by dark shutters and manicured shrubs. A concrete path leads to the welcoming red front door. Lush greenery and flower beds enhance the outdoor space, complemented by a peaceful sky.

Home in Simpsonville

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.

A speakeasy-style room features a circular table surrounded by folding chairs, offering ample seating for games. A fireplace with a dark brick surround adds warmth, while green walls complement the unique wall art displaying vintage images. A bar area is positioned alongside for refreshments.

4.98 out of 5 average rating, 44 reviews

Bourbon Trail, Hot Tub, Speakeasy, 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.

The exterior of a spacious two-story home is presented at dusk, featuring a welcoming porch with ample seating. Lush greenery frames the property, and soft lighting emanates from the windows, inviting guests to enjoy the charm of Southern hospitality.

4.94 out of 5 average rating, 16 reviews

Historic Centrally Located Gem •Hot Tub •Sleeps 10

Enjoy this beautifully renovated 4 bedroom (5 beds) 3 full bathroom home. It is your gateway to the best of Kentucky Bourbon Country. Nestled between Louisville, Lexington, Lawrenceburg, and Frankfort, you'll be minutes from legendary distilleries like Jeptha Creed, Bulleit, Four Roses, Wild Turkey, and Buffalo Trace.