Vakantiewoningen in Shelbyville

Bourbon Trail*River Views*Hot Tub*Sauna*EVSE*WiFi

Welcome to River Whisper. The remodeled riverfront house offers the perfect blend of organic modern decor and unparalleled comfort. Experience luxury with top-of-the-line features, a hot tub, and a barrel sauna, all overlooking the beautiful Kentucky River. Located in the heart of Bourbon Trail, with easy access to many renowned distilleries, including Buffalo Trace and Woodford Reserve. Explore historic downtown Frankfort, Cove Spring Park, river boat tours, kayaking, fishing, hiking and more.

Bourbon, Bridles & Birdies Retreat

We would LOVE to welcome you to Bourbon, Bridles & Birdies Retreat! Nestled in a quiet & peaceful neighborhood in the historic district of downtown Shelbyville, this FAMILY-FRIENDLY home offers unique dining experiences, seriously good shopping & the fairgrounds less than a mile walk away. Do you have plans in the big city?This thoughtfully laid out, detail-packed home will be your perfect retreat to relax. Please see "The Space" section for all the amazing attractions Shelbyville has to offer!

Cottage On Crooked Creek

A tranquil cottage nestled in the lush countryside and situated right along the Bourbon Trail, this completely renovated rare find is located center of Lawrenceburg, Frankfort and Shelbyville and only 12 min to I-64. With five main bourbon distilleries just 30 min, local wineries within a stone's throw, Churchill Downs and Keeneland Racecourse equidistant and Taylorsville Lake nearby there is little left to be desired when staying here. This is the perfect spot to relax with family and friends.

Home near the Highways

Comfortable, clean home in a quiet neighborhood Garage and driveway parking 3 Kings, 2 Queens, 2 Full beds, 2 Futons, 1 Loveseat Sleeper Sofa, 1 Couch Individual coffee makers in rooms with complementary coffee Peaceful front porch. Back and patio with gas & charcoal grills and green view Pet Friendly. Scroll down to "Other Things to Note" for more info. 2.5 miles to I-265. 3 miles to I-64. 20-30 minutes to most places in Louisville. 1 mi to a fuel, groceries, restaurants & banking

Backyard Bourbon Retreat

Your family will be close to everything when you stay at this centrally-located place. This is a beautiful two bedroom two full bath home packed with a ton of amenities! Only minutes from several distilleries such as Buffalo Trace, Jim Beam, Woodford Reserve, Ancient Age and Four Roses just to name a few! There is a fully fenced in yard with a deck looking into a 1/4 acre landscaped backyard. Great for sitting back and relaxing with a Kentucky beverage. Welcome to the Backyard Bourbon Retreat!

Pool*Pickleball Bldg*HotTub*Speakeasy*BourbonTrail

Welcome to the "Bourbon Barrel Retreat" where this truly unique property offers a one-of-a-kind getaway. This newly renovated 5-bed, 3 full bath ranch boasts two additional buildings on the property to provide a Kentucky experience like no other. Immerse yourself in the ambiance of the Bourbon Speakeasy or spend time at the Pickleball Sports Lounge. Unwind and relax however you would like! An ideal location where you are a short drive to Bardstown, Louisville, Lexington, Mammoth Cave and more!

Heart of the Trails

Relax with the whole family at this New peaceful place to stay. At the Heart of the Trails you are right in the middle of all the bourbon trails & Wineries In Frankfort & min. to Lawrenceburg & Versailles. We are right next to the highway can be at any surrounding towns in a few! You also have Juniper Hills water park with playground barbecueing & golfing. We also have the game farm educational center to visit all the animals & fishing. Also bourbon tours everywhere. All one level home.

The Lady Jinx Home - 3 BR/2.5 Bath - Entire Home

“The Lady Jinx” is a renovated 3 BR/2.5 Bath, Princess Anne-style Home built in 1895. This 2-story has tons of character from the detailed wood trim to the stain glass windows to the original interior doors to the gorgeous wood floors. The home is located in downtown La Grange, the only town in America that has an active train running along it’s Main Street, & is within walking distance to restaurants, shopping boutiques, museums, parks and entertainment with being only one block away!

Bourbon Speakeasy 6BR Estate · Hot Tub · Sleeps 14

Bourbon Trail Hideaway – Where Luxury Meets Fun Gather your favorite people and settle into this stunning 6-bedroom, 4.5-bath modern farmhouse, built for connection, comfort, and fun. With room for up to 14 guests, enjoy spacious living areas, relaxing spa amenities, and entertainment everyone will love. Whether you’re here for the Bourbon Trail or simply to unwind together, this home delivers an unforgettable stay. 🥃 Reserve your dates today and make it a trip to remember.

Lakefront Horse Farm | Sleeps 12 | Bourbon Trail

Experience Kentucky horse country from your own private lakefront retreat. Nestled on a working Thoroughbred farm and sleeping up to 12 guests, this spacious home is perfect for Bourbon Trail weekends, family gatherings, golf trips, and peaceful escapes in the Bluegrass. Conveniently located between Louisville, Lexington, and Frankfort. Relax on the porch bed swing, gather around the fire pit, or enjoy air hockey, foosball, cornhole, bucket golf, and a basketball shootout.

Quiet Downtown Maple Cottage Gem

Welcome to our charming Maple Cottage in the heart of a peaceful downtown neighborhood. This 3-bedroom, 1-bathroom home has undergone a complete remodel, ensuring a cozy and comfortable stay in Shelbyville. Whether you're here for a weekend getaway or an extended stay, this cottage offers all the amenities you need. The fully fenced backyard offers privacy and space for relaxation and smores over the fire pit. Your Shelbyville adventure begins here!

LUX Farmhouse | HotTub | Firepit | GameRm | 5 Acre

Brand-new luxury farmhouse on 5 private acres in the heart of Kentucky bourbon country. This 4BR retreat sleeps 12 and is built for unforgettable group getaways, with a massive game room, full bar, pool table, shuffleboard, foosball, poker table, 85” TV, covered 6-person hot tub, huge firepit, outdoor games, and a fully stocked chef’s kitchen. Minutes from Buffalo Trace, Bulleit, and Jeptha Creed. Send us a message with any questions!