Holiday houses in Shelby County

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.

Cottage On Crooked Creek

A tranquil cottage nestled in the lush countryside and situated right along the Bourbon Trail, this completely renovated rare find is located center of Lawrenceburg, Frankfort and Shelbyville and only 12 min to I-64. With five main bourbon distilleries just 30 min, local wineries within a stone's throw, Churchill Downs and Keeneland Racecourse equidistant and Taylorsville Lake nearby there is little left to be desired when staying here. This is the perfect spot to relax with family and friends.

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.

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 that flows 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.

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.

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.

Hidden View Cabin

Welcome to Hidden View Cabin, a delightful cabin where seeing wildlife and listening to the sounds of nature are yours to enjoy! Take the scenic drive down the gravel lane to this private and peaceful place located among pine trees and overlooking a one acre pond. Whether you have come to relax and get away from it all or want to visit the many attractions throughout central Kentucky this is the place for you. Only 20 minutes from Lawrenceburg.

6 Private Acres! HotTub/Theater | Gamerm | Arcade

Minutes from Kentucky's most iconic distilleries, Oak & Mash is a private six-acre log cabin retreat designed for unforgettable group getaways. Relax in the covered hot tub, enjoy movie nights in the home theater, gather in the bourbon lounge, challenge friends to pool, shuffleboard, or arcade games, and unwind around the fire pit beneath the stars. With indoor and outdoor entertainment for every season, there's something for everyone to enjoy.

Sip on bourbon in the hot tub! +hiking & game shed

A charmingly unique taste of KY waits for you at this peaceful log cabin! Perfect for those wanting to explore the 🥃Bourbon Trail🥃 or other nearby tourist attractions, While still featuring plentiful amenities on site, such as: - A hot tub - Private 1/4 mile hiking trail - Game shed - Fire pit - Covered porch - Wooded picnic area And more! Your next adventure is just a peaceful countryside drive away at the Kentucky Bourbon Den!

Private A-frame Cabin | Hot tub, Firepit & Views

Welcome to Peletah Escape — our family’s cherished retreat nestled in Kentucky’s rolling hills. This cozy cabin offers sweeping views, a wraparound porch, hot tub, fire pit, game room, and plenty of space to relax. Inside, you’ll find rustic charm with modern comforts, from a fully stocked kitchen to comfy beds and a bourbon bar. Whether you're here to unwind or explore, Peletah Escape is your perfect Bluegrass getaway.

Country Retreat on Bourbon Trail - Fire Pit - King

Surrounded by farmland, but close to Louisville, Frankfort, distilleries, and shopping! Start your morning on the front porch with a cup of coffee or tea and watch the horses across the way. Hop over to Louisville for the day, and afterwards, your tranquil country oasis awaits! Grill out and chill by the fire pit. Do some star gazing. Or just enjoy the peace of Kentucky’s countryside.