Holiday rentals in Shelby County

6 Private Acres! HotTub/Theater | Gamerm | Arcade

Minutes from Kentucky’s iconic bourbon distilleries, Oak & Mash is a private six-acre log cabin retreat made for memorable group getaways. Relax in the covered hot tub, enjoy the home theater and bourbon lounge, or challenge your crew to pool, shuffleboard, arcade games, and a private 4-hole disc golf course. End the day gathered around the fire pit under the stars. With indoor and outdoor entertainment for every season, Oak & Mash is the perfect home base for your Kentucky Bourbon Trail getaway

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!

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!

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

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.

High Rollers' Retreat w/pool and Pond

Experience an unforgettable stay at our exquisite 8BR, 8BA Speakeasy retreat, nestled in 14 acres of private, fenced-off tranquility. This adult-only haven for 16 guests, is accentuated by a dark academia aesthetic, our property channels a masculine, speakeasy vibe, peppering your stay with an irresistible dash of intrigue and sophistication. Take a moment to unwind, pour a glass of your preferred bourbon or wine and disconnect from the world. Your euphoric getaway starts here.

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.

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.

Cottage of Eden. Bourbon Trail Stay in Shelby Co.

Listen to the birds sing as the walkway guides you to your quaint cottage getaway. Take in nature, as you’re surrounded by trees, near our sweet chicken coop and a creek down from the deck - all while only 10min from town. Special touches were added of Kentucky Derby photos, books, kitchenware, Bourbon Trail glasses and bourbon barrel heads with local distilleries. The dining table top is even made of wood from Shelby County’s own Bulleit Distilling Company.

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 Country Farm Stay | 6BR | Updated 2026

Recently Updated 2026! Bring the whole family to this spacious retreat on 5 acres with plenty of room to relax and have fun. Enjoy a pond, swimming pool, fire pit, pool table, ping pong, and multiple gathering spaces—too much to list! The pool opens on Memorial Day. A private, lighted pickleball or basketball court with nearby access. Less than 5 minutes from town and local winery and bourbon distillery. Newly remodeled, updated wifi.