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Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views

Welcome to your Bourbon Trail getaway in Waddy, KY- perfectly located near Lawrenceburg, Shelbyville, Frankfort, and Versailles with easy I-64 access. This charming 3-bedroom, 2-ba home features hardwood floors, a fully equipped kitchen, jacuzzi tub, high-speed Wi-Fi, and self check-in. Relax on the front porch rocking chairs, unwind on the new patio, or enjoy breathtaking sunsets. Ideal for families, couples, or remote workers seeking a peaceful Kentucky escape close to horse country. Book now!

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!

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!

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!

Hot Tub | Airbnb KY Country | Near Wine & Bourbon

🥃TRAILSIDE COUNTRY HAVEN🥃 in Bagdad, KY. ★★★★★ · 3 BR · 5 Beds · 2.5 Baths Welcome to TRAILSIDE COUNTRY HAVEN, A BEAUTIFUL HOME professionally managed by Excellent Vacay Stays. This home is nestled IN THE HEART OF the countryside along THE BOURBON TRAIL in Shelby County. As your host, Iris, I'm excited to share this picturesque haven that offers a serene and private wooded area. Discover why our guests love the multiple decks and patios for outdoor enjoyment!

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!

Charming 4 Bedroom classic home bourbon trail!

Comfortable, newly furnished home located in downtown Simpsonville. This is brand new to AirBnB. Whether you are going down the Bourbon trail or you just want to be near I64 and Louisville, this home is the place for you. Fun, homey well decorated this place offers family fun with Fire pit, backyard and patio. High speed 300mb internet for those workers on the go.

Cozy Cottage | Hot Tub + Holiday Ready

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.