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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.

Historic Downtown~Heart of Bourbon Trail

The Washington Belle is an historic home, freshly renovated with all the modern conveniences, centrally located in Shelbyville, Kentucky. She's the perfect base from which to explore the distilleries of the Bourbon Trail, with easy access to Louisville and Lexington. There are multiple restaurants, cafes, bourbon bars and antique stores in easy walking distance. Boasting two large living areas, three large bedrooms (including a master with ensuite), 2.5 baths, and private off street parking

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!

Farm House - near Bourbon Trail & Pet Friendly

Late 1800's farm house on a 155 acre working family farm located in the heart of the Bourbon Trail. It is a unique experience to stay on our farm where we raise non-GMO corn that goes into producing bourbons here in Kentucky. The farm is rural and private, but convenient to Louisville, distilleries and many other local attractions. We are located only 10 minutes from the Gene Snyder Freeway in Louisville and 10 minutes from the Outlet Shops of the Bluegrass and 15 minutes from Shelbyville.

Countryside On the Bourbon Trail, 22 Quiet Acres

Welcome to Sea Glass Farm. 1900's restored farmhouse with tons of charm! 22 acres of privacy. Cows may be present in pasture. The heart of The Bourbon Trail, the scenery and wildlife will not disappoint. The location is perfect for a rural getaway or relaxing stop on your Bourbon Trail experience. Minutes from shopping and restaurants; situated between I-64 and The Bluegrass Parkway. This place has been a dream of ours and we look forward to sharing it with you. Hosted by the owners.

*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!

Lux Home Near Lou Lex | Hot Tub | Games | Bourbon

Nestled in the heart of Kentucky’s Bourbon Trail, our spacious farmhouse is the perfect sanctuary for large groups to relax. Enjoy stunning sunrises from the front porch, soak in the hot tub, and make memories in the game room. Conveniently located just a short drive from the Bourbon Trail, this home sits in the serene countryside between Louisville and Lexington, offering the perfect blend of convenience and Southern charm. Book For Lasting Memories Bagdad—See Details Below!

Cozy Kentucky Winter, Bourbon Trail, Location!

♡ Meet The Blue Belle: a beautifully restored 1880s cottage ON the Bourbon Trail, nestled on a peaceful block in the heart of Shelbyville. Start your day with a coffee on the back deck, make s'mores by the fire pit, cook dinner in the fully stocked kitchen, & cozy up in the living room for movie night after a long day of exploring & bourbon! A short drive to Louisville, Lexington, & Frankfort and other great areas. Comfortably sleeps 8. Perfect for families & couples!

Central Bourbon Trail Gem | 2 Kings | Fire Pit

Oak is the upper unit of The Copper & Oak, a beautifully restored 1909 home in the heart of Shelbyville. This stylish two-bedroom retreat pairs historic charm with modern comfort, offering a bright living area, fully equipped kitchen, and two thoughtfully designed king suites. Just steps from local shops, restaurants, and the Bourbon Trail, it’s the perfect home base for exploring Shelbyville or enjoying a relaxed weekend getaway.

Cozy Crestwood Cottage w/ Hot Tub – Sleeps 8

Book your holiday escape at Crestwood Cottage! Our cozy retreat features a decorated Christmas tree, festive touches, private hot tub, dedicated workspace, and a fenced backyard perfect for pets or enjoying crisp fall and winter air. Just minutes from Louisville and bourbon distilleries—ideal for holiday gatherings, family trips, or winter getaways.

Bourbon Trail Home with Hot Tub and Speakeasy

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.

Comfortable sleek home bourbon trail

Whether you are going to the racetrack, visiting the bourbon trail, going to a PGA event, or just enjoying the beauty of Kentucky this is a wonderful place to stay. New construction clean contemporary design, in the heart of the bluegrass. Close to Louisville, but located in the low crime feel good community of Simpsonville.