Holiday rentals with a hot tub in Shelby County

Bourbon Trail*Hot Tub*Sauna*Mini Golf*WiFi*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.

Luxury modern barn home on a Kentucky horse farm

One-of-a-kind Kentucky barn home nestled on 43 rolling acres. The modern design of this black barn is restful and sophisticated. Wake up and enjoy your coffee overlooking the pastures with all the modern amenities one would expect—2 King beds, 2 twins, 1 Bath with soaking tub and double walk in rain shower, full kitchen, & laundry. Enjoy beautiful mornings watching the sunrise with a hot cup of coffee in your hand on the porch. Soak in the hot tub or delight in a cozy fireside conversation

Private Estate on Bourbon Trail : KY Derby : Pool

Welcome! Bring the whole family to Horse & Bourbon Country with plenty of room for fun. Enjoy a day at any of the local Distilleries with Bulleit, Wild Turkey, Buffalo Trace and many more within a 25 minute drive and then come back to a relaxing sunset on a spacious back deck with a view of the pool, hot tub and fully stocked 1 acre pond. You can enjoy a night of Billiards, Shuffleboard or a movie inside the Theatre room. Situated between Churchill and Keeneland there is something for everyone!

Red Bridge Retreat

Red Bridge Retreat sits on 5 beautiful tranquil acres in a suburb of Louisville KY but within 30 min to most major local events. Elegant & stylish decor throughout. This 4 Bedroom 3 full bath private home has, deck off kitchen w/ Blackstone & gas grill, covered patio w/ HOT TUB, covered fire pit area, beautiful & fully equipped kitchen, game room w/ bumper pool & Pac man. Tree lined driveway w/ lovely landscaping all around. This home even has a bourbon themed lounge to hang out & relax.

Cabin with spectacular views, creek, & hot tub

Located on beautiful Brashears Creek in the heart of Bourbon Country, this loft style cedar cabin makes a great central location to visit some local distilleries and wineries. It is also a great place to stay for anyone who might be in the area for a horse show or interested in antique shopping along Shelbyville's historical Main Street. My personal favorite thing to do at the cabin is enjoy the creek. The water level fluctuates significantly depending on the amount of rainfall received.

2025 KY Derby 30 min Away ~ Bourbon Trail ~ Hot Tu

Step into the gorgeous and unique Shelbyville 3BR, 3Bath home, offering a perfect base for everyone coming to see the exciting saddle-horse farms, horse shows, or stopping by along the Bourbon Trail. If all Shelbyville attractions aren't enough for you, the private, in-house art gallery featuring the artwork of renowned local artists will leave you mesmerized. ✔ 3 Comfortable Bedrooms ✔ Private Art Gallery ✔ Gourmet Kitchen ✔ Backyard ✔Smart TVs ✔High-Speed Wi-Fi Learn more below!

Kentucky Bourbon Log Cabin

Are you ready to get away from it all? Experience KY Country Living right on the Bourbon Trail! Our beautiful log home on a working farm is a perfect retreat! Featuring exposed logs, vaulted ceilings, fully equipped kitchen, large outdoor areas, fire pit, gas grill, game room with pool table and hot tub. This is a working farm with horse, cattle, and amazing views!! Close to several distilleries, local restaurants, horse farms, orchards and more.

4BR Buffalo Trace -Hot Tub •Firepit •Sunsets

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

Hot Tub, 10 min to Bulleit

Escape to our serene haven nestled in the heart of the Kentucky Bourbon Trail. This inviting property offers the perfect home base for your bourbon tasting adventures. The Bourbon Bungalow is located in a rural/residential area across the street from Guist Creek Lake in the charming town of Shelbyville. We are midway between Louisville and Lexington and perfectly situated for visits to a plethora of distilleries.