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.

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.

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.

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.

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!

Hot Tub | Bourbon Trail | Poker Room | Game Rm

Welcome to Magnolia Bourbon Manor, a beautifully restored historic home nestled in the heart of Kentucky’s bourbon country. Just three minutes from downtown Shelbyville, this charming property offers the perfect blend of vintage elegance and modern comfort, making it an ideal retreat for travelers seeking both relaxation and adventure.