Vacation 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.

Private Estate on Bourbon Trail w/ Beautiful 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!

The Miles Around Kentucky Cottage| Hot Tub

Welcome to The Miles Around Kentucky Cottage! Relax and rejuvenate in our cozy cottage nestled in a private area yet still close to stores, restaurants and many tourist attractions including 1.5 miles to the Bluegrass Outlet Mall. Only one mile from small town businesses including Little Mount Lavender, Brick and Mortar Coffee, Weathered Oak, The Lovely Fig, Dos Mundos and El Nopal. 25 miles to Buffalo Trace and downtown Louisville attractions. Centrally located to Louisville & Lexington.

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!

*Distilleries close by* Hot tub*Firepit

Welcome to this beautiful, new 4 bedroom, 3.5 bathroom home ready to be the place for your bourbon trail stay! Centrally located just outside of Louisville. This home is less than 30 minutes from downtown Louisville where you can enjoy multiple distilleries, the Louisville Slugger Museum & Factory, Churchill Downs, the Fair & Expo, and just a short drive to Four Roses, Lexington and so much more! Air Hockey, hot tub, Golden Tee and fire pit are all waiting for your group to enjoy!

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.

Bourbon Trail Getaway~Hot Tub, Pets OK, Game Room

✨Welcome to Bourbon Barrel Escape — your perfect launch pad for exploring Kentucky’s legendary Bourbon Trail! Located in charming Shelbyville, our stylish, fully furnished home is minutes from two local distilleries and less than an hour from 30+ more. Whether you’re sipping bourbon, soaking in the hot tub, or playing a game of pool, this retreat has everything you need for a fun and relaxing getaway

Arcade | Fishing Pond | Cabin on Farm | Slps 12+

Reconnect and recharge at The Rec Farm—a private 12+ acre retreat with a cozy 3BR log cabin, lake views 🌅, hot tub ♨️, fire pit 🔥, and game-filled Rec Barn. Sleeps up to 13 with room to spread out and play. Enjoy an arcade, ping pong, ski ball, and more in the ultimate game barn. Just minutes off I-64 but worlds away from everyday life—perfect for family getaways, friend trips, or team retreats!