Vacation rentals in Shelby County

4.98 out of 5 average rating, 124 reviews

The spacious living area showcases original wooden beams and exposed brick walls. A round plush couch surrounds a glass coffee table, while a projector hangs above for movie nights. The vibrant area rug adds a cozy touch to the open layout.

Loft in Shelbyville

Close to Buffalo Trace/Transpo available-Must See

Best place to stay on the Bourbon Trail FEATURED on HGTV! Swanky! Stunning! Spectacular! You'll be in a top-floor loft overlooking downtown Shelbyville and perfectly situated in the heart of the Bourbon Trail! Incredible place to stay for Derby, Keeneland, PGA or local weddings and events---if you can pry yourself away from here! We specialize in making your stay an over-the-top experience and are happy to arrange chauffeured transportation, private chef accommodations, and dinner reservations.

5.0 out of 5 average rating, 25 reviews

Bourbon, Bridles & Birdies Retreat

We would LOVE to welcome you to Bourbon, Bridles & Birdies Retreat! Nestled in a quiet & peaceful neighborhood in the historic district of downtown Shelbyville, this FAMILY-FRIENDLY home offers unique dining experiences, seriously good shopping & the fairgrounds less than a mile walk away. Do you have plans in the big city?This thoughtfully laid out, detail-packed home will be your perfect retreat to relax. Please see "The Space" section for all the amazing attractions Shelbyville has to offer!

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!

4.97 out of 5 average rating, 29 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

5.0 out of 5 average rating, 31 reviews

A light-filled living area features warm wood flooring and a decorative area rug. A cozy seating arrangement is centered around a coffee table, with a fireplace made of exposed brick as a focal point. Natural light streams through the windows, illuminating the inviting space.

Home in Pleasureville

Bourbon Trail Country Getaway

Escape to the peaceful countryside and unwind in our restored farmhouse surrounded by rolling farmland. This secluded retreat with three gas fireplaces is ideal for romantic getaways, bourbon enthusiasts, or family-friendly stays. Whether you’re sipping morning coffee on the porch, gathering around the firepit, enjoying some friendly competition in the game barn, or exploring the nearby Bulleit Bourbon Distillery on the Bourbon Trail, you’ll find tranquility and adventure in equal measure.

4.99 out of 5 average rating, 67 reviews

Farm stay in Shelbyville

Beautiful Farm Stay on the bourbon trail!

This memorable place is anything but ordinary. Enjoy the picturesque views from the farmhouse of the pastures. Watch as the sheep and horses graze. On the hour you can hear the sound of church bells. When the wind is right, the smell of mash from local distilleries wafts through the air. Make one of a kind memories on our beautiful farm. Included in your stay are fresh farm eggs (when available), enough coffee, creamer, sugar for the first morning, and 6 bottles of water and farm tour.

A bright living area features two white sofas, accented with colorful throw pillows. A rustic wooden coffee table sits centrally, displaying drinks. Two plaid armchairs are positioned across from the sofa, and vibrant artwork of cows adorns the wall, enhancing the inviting decor.

5.0 out of 5 average rating, 13 reviews

Hitching Post on the Bourbon Trl

The Hitching Post on the Bourbon Trail – Spacious Shelbyville retreat near charming downtown & walkable to the famous Horse Show. Minutes from Louisville & centrally located to top distilleries. Enjoy a man cave with poker, darts, shuffleboard & big screen TV, plus a screened porch for coffee or bourbon. Kids will love the playhouse over a stream in a fenced yard. Located in a safe, scenic community in the Saddlebred Capital of the World—your perfect base for bourbon & horse country!

5.0 out of 5 average rating, 33 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.

4.98 out of 5 average rating, 62 reviews

A two-story guest house is situated amid lush green grass and shade trees. The exterior features a combination of light siding and dark accents, with a covered porch furnished with chairs. Windows allow natural light to engage the interior, enhancing the peaceful rural setting.

Farm stay in Shelbyville

Annola Farm Guest House

Stay and be delighted with this newly renovated two-story guest house which adjoins our 11-stall horse barn. Framed by covered porches and shade trees, our guest house is a wonderful place to unwind and relax during your stay in beautiful central Kentucky. The best of both worlds--a lovely rural setting situated only minutes from the interstate, making travel to Churchill Downs, Valhalla Golf Course, and other attractions in nearby Louisville and Frankfort a breeze.

4.91 out of 5 average rating, 56 reviews

The spacious living area features large windows allowing ample natural light. Elegant details include high ceilings and exposed brick walls. A plush sofa is arranged around a coffee table, while a dining area with a wooden table is visible in the background.

Loft in Shelbyville

The Lucky Penny Downtown Loft - Central Location!

Experience timeless charm in this beautifully renovated mid-19th century Airbnb in the heart of Shelbyville. With soaring 14 ft ceilings, this historic gem combines classic architecture with modern amenities. Centrally located, it offers convenient access to local attractions, dining, and shopping. Enjoy a blend of elegance and comfort in a space that honors its rich heritage while providing all the contemporary conveniences you need for a memorable stay.

An aerial view showcases a spacious estate with bright outdoor lighting highlighting the landscaped grounds. A recreational area featuring basketball courts and seating is visible, offering ample space for outdoor activities, while the elegant façade of the home provides an inviting presence.

4.99 out of 5 average rating, 69 reviews

Kentucky Estate: Speakeasy, Theater & Sleeps 20

Oak & Ember Estate is an 8-bedroom Kentucky retreat sleeping up to 20 on 5 private acres. Hidden speakeasy with poker table, private cinema, converted garage game room with putting green and billiards, hot tub, pickleball court, and a gourmet kitchen built for groups. 30 minutes from Churchill Downs. The perfect home base for bourbon trail adventures, Derby weekend, family reunions, and corporate retreats. Guests say they never wanted to leave.