Orlofseignir í Shelbyville

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!

On The Rocks

Ultimate in privacy, yet two minutes from downtown Frankfort! This cabin-style home (think Gatlinburg!) sits on three wooded acres. Long, rambling decks on three sides (one covered, one fully screened, one open air). Our adjacent farm surrounds the property, making it even more private. This home sits high on a bluff above downtown Frankfort & the Kentucky River (our farm borders on the river). Just three miles to Buffalo Trace Distillery (if you could fly, it's way closer than that!)

Lux HorseFarm*Pklball*SwimSpa*Sauna*Golf*Speakeasy

Escape to your own private 5 acre horse farm, surrounded by rolling hills and amazing views for a rare one-of-a-kind-getaway. This newly renovated 7-bed, 4 full bath estate blends luxury living with endless amenities to provide a Kentucky experience like no other. Enjoy the Golf and Pickleball Sports Lounge or slow down to sip and savor in our authentic Speakeasy. Unwind and relax however you would like! An ideal location where you are a short drive to Louisville, Frankfort, Lexington and more.

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!

Brown Ave Bourbon Trail & Beds- Shelbyville, KY

Welcome to Brown Avenue Bourbon and Beds, a beautifully renovated 1950's charmer on the Bourbon Trail, near the Shelby County Fairgrounds & just minutes from downtown Shelbyville. Start your day w/ coffee on the front porch swing, enjoy an afternoon snack on the back deck, cook dinner in the fully stocked kitchen & cozy up in the living room for movie night after a long day of exploring! A short drive to Louisville, Lexington, Frankfort, KY Derby and PGA Championship 2024 @ Valhalla! Sleeps 6

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

Hot Tub ~ Art Gallery ~ Bourbon Trail ~ KY Derby

Soak in your private hot tub, step into a one-of-a-kind art gallery, and wake up 30 minutes from the Kentucky Derby. This renovated Victorian cottage blends spa-level comfort with local artistry, the perfect base for Bourbon Trail adventures, horse show weekends, or a group getaway nobody will forget. Three ensuite bedrooms, a gourmet kitchen, and a covered porch await. ✔ Hot Tub · Art Gallery ✔ 3BR/3BA Ensuite · Bourbon Trail ✔ KY Derby 30 min · BBQ Porch ✔ Wi-Fi · Smart TVs · Self Check-In

Close to all the popular distilleries Perfect Spot

Ultra Luxury downtown 2 BR loft, spacious enough for 5 adults. Located in quaint Downtown Shelbyville, KY, you are in the heart of the bluegrass near major distilleries and race tracks and close to coffee shops, restaurants and bars right on the same block. You can't go wrong with this unique loft for its decor and proximity to everything. Close to all distilleries on the eastern part of the Trail and centrally located to all distilleries in the state. Come see what this space has to offer

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.

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.

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