Places to stay in Shelbyville

Guest suite in Shelbyville

A spacious outdoor area features a well-maintained stone pathway leading through lush greenery. Flower beds with vibrant blooms are flanked by manicured grass and a wooden fence, offering a serene rural environment. A covered porch provides a shaded space to relax and enjoy the view.

5 out of 5 average rating, 95 reviews

Comfortable Charm on the Bourbon Trail

You’ll be charmed by this adorable place to stay, close to the interstate, making travel to Valhalla Golf Course, bourbon distilleries, Churchill Downs, and other attractions in nearby Louisville a breeze. We are in a beautiful rural setting, just right for relaxing. Our space has its own private entrance with a comfortable living room and private bathroom downstairs, and features a loft with queen bed and desk. There are a microwave, coffee maker, and fridge available for your convenience.

5 out of 5 average rating, 213 reviews

The exterior of the stone cabin is framed by lush greenery and flowering plants. Sunlight casts soft shadows across the textured stone walls. A decorative statue stands on a pedestal near the entrance, complementing the natural surroundings.

Cabin in Louisville

Historic Cabin by Bourbon Trail

Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

4.91 out of 5 average rating, 122 reviews

A blue sign featuring the name 'Christopher Crossing' in decorative lettering. The sign is framed by white posts, surrounded by green foliage. A gravel path is visible in the background, suggesting a serene entrance to the community.

Condo in Shelbyville

Kentucky bourbon, horses, cozy condo

Welcome to your home away from home! Great place to stay while visiting local establishments, horse shows, bourbon trail, extended work stay or family. Work or Play this adorable condo was recently renovated and has all the comforts of home! King bed in main bedroom with full bath, queen size guest bed and 2nd large bathroom, wifi, fully furnished kitchen along with washer and dryer. Parking at your entrance with no steps! Just minutes from I64, groceries, restaurants and shopping!

4.99 out of 5 average rating, 153 reviews

Barn in Mount Eden

Sweet Hollow Farm

Sweet Hollow Farm is located near Taylorsville Lake. 30 miles from Louisville, 40 miles from Lexington and 25 from Bardstown. We have a small farm with a studio barn apartment. Private entrance with full bath. We also have a beautiful pool that we share with our guests. There is a horseshoe pit, fire pit and multiple outdoor seating areas. Kids and dogs welcome. We even have space for horses and boats. We can offer peace and quiet, a clear view of the stars and hummingbird theatrics.

4.93 out of 5 average rating, 221 reviews

An open space features a large glass garage door adorned with a view of greenery, allowing natural light to fill the area. Two metal stools are positioned at a small wooden bar against the wall, providing a cozy spot for relaxation or meals.

Treehouse in Georgetown

Treehouse with TWO outdoor tubs by the creek!

Welcome to your romantic treehouse getaway! Nestled among the trees, this one-bedroom treehouse is the perfect spot if you're looking for a unique & unforgettable experience. The treehouse features a large glass rolling garage door allowing stunning views of the sunset, but the highlight is undoubtedly the double tubs overlooking the creek. ✔ Queen Bed ✔ Outdoor Deck with Seating ✔ Double Outdoor Bathtubs ✔ Outdoor Shower ✔ Composting Toilet ✔ Creek Access ✔ Indoor Cooking Station

Guesthouse in Shelbyville

A well-defined pathway is illuminated by small lanterns, guiding guests toward the cottage nestled among trees. The gentle glow from the lights contrasts with the surrounding dusk, creating a serene approach to the inviting space.

4.97 out of 5 average rating, 112 reviews

Cottage of Eden. Bourbon Trail Stay in Shelby Co.

Listen to the birds sing as the walkway guides you to your quaint cottage getaway. Take in nature, as you’re surrounded by trees, near our sweet chicken coop and a creek that flows down from the deck - all while only 10min from town. Special touches were added of Kentucky Derby photos, books, kitchenware, Bourbon Trail glasses and bourbon barrel heads with local distilleries. The dining table top is even made of wood from Shelby County’s own Bulleit Distilling Company.

4.99 out of 5 average rating, 571 reviews

Cabin in Lawrenceburg

Bourbon Trail Cabin on the Farm

Recognized by AirBnB as the “2021 Top New AirBnB in the State of KY”!Overlooking rolling hay fields, and surrounded by wooded farm land, this cabin features barn wood walls, hardwood floors, handcrafted bourbon barrel sink, king bed, leather sleeper sofa, and custom built kitchenette. Located on a working cattle farm, see cows, goats, a donkey and horse, & our pet free-range pig! In the heart of the Bourbon Trail in the home of Wild Turkey and Four Roses.

5 out of 5 average rating, 23 reviews

Loft in Shelbyville

The Lucky Penny Downtown Loft - Central Location!

Experience timeless charm in this beautifully renovated mid-19th century Airbnb in the heart of Shelbyville. With soaring 14 ft ceilings, this historic gem combines classic architecture with modern amenities. Centrally located, it offers convenient access to local attractions, dining, and shopping. Enjoy a blend of elegance and comfort in a space that honors its rich heritage while providing all the contemporary conveniences you need for a memorable stay.

4.98 out of 5 average rating, 106 reviews

Loft in Shelbyville

LeCoop Loft close to all the popular distilleries

Ultra Luxury downtown 2 BR loft, spacious enough for 5 adults. Located in quaint Downtown Shelbyville, KY, you are in the heart of the bluegrass near major distilleries and race tracks and close to coffee shops, restaurants and bars right on the same block. You can't go wrong with this unique loft for its decor and proximity to everything. Close to all distilleries on the eastern part of the Trail and centrally located to all distilleries in the state

Superhost

A graciously restored house features a distinctive green exterior with white trim and a covered porch. Columns support the balcony above, while the entryway is framed by a symmetrical arrangement of windows. Lush greenery surrounds the entrance, enhancing the inviting appearance.

4.75 out of 5 average rating, 112 reviews

2 Bed/2.5 Bath Restored Beauty - Pistachio Palace

Built 1904 and recently lovingly restored. Just 2 blocks off historical Main Street in Shelbyville with great antique and coffee shops, as well as some favorite pubs and restaurants. In the middle of the Bourbon trail and Horse country, short drive to the new Convention Center and the Outlet Mall. This neighborhood is in the midst of gentrification. 2 Queen Beds, one Roll-away, pack-n-play & high chair. Absolutely no pets, including service dogs.

4.98 out of 5 average rating, 166 reviews

Dome in Mount Washington

My Old Kentucky Dome

An elevated camping “glamping” experience. This brand-new one of a kind geodesic dome is located on a private road that leads you to an overlook featuring one of the most beautiful countryside views in Kentucky. While this getaway experience is nestled deep in the woods, it is also a close drive to all the conveniences you can imagine. This is an off the grid outdoor experience with a ½ mile gravel road including a steep hill. AWD or 4WD advised.

4.96 out of 5 average rating, 405 reviews

A charming log cabin is surrounded by lush greenery, featuring a porch with rustic wooden railings. A brick chimney rises from the side, complementing the gabled roof. The outdoor area includes a pathway leading to the cabin, set amidst the serene woodland landscape.

Cabin in Mount Eden

Bourbon Country Cabin

Nestled in the Heart of Bourbon Country sitting on 80 acres of Kentucky woodlands this charming loft style cabin makes a great central location to visit all the local distilleries on the Kentucky Bourbon Trail! Enjoy exploring the walking trails, creek, and the property while you stay in a peaceful cabin in the woods! Check out our other listing too if you have a large group and would like to book both rentals. Bourbon Country Cottage

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4.91 out of 5 average rating, 11 reviews

Home in Simpsonville

Eastern Sky

ChloeRating, 5 stars2 weeks ago

We were in town for the Kentucky Ren Faire and it was a great location! Beautiful and peaceful location.

Superhost

The kitchen features modern stainless steel appliances, including a refrigerator and microwave. Elegant pendant lights hang above an island with a granite countertop. White cabinetry complements the light wooden flooring, creating a bright and functional cooking space. A door leads to an outdoor area.

4.82 out of 5 average rating, 17 reviews

Charming Home in Historic Downtown Shelbyville

AnitaRating, 5 stars5 days ago

The place was beautiful—peaceful, clean, and exactly as described. Shannon was an amazing host—kind, responsive, and easy to communicate with. I appreciated how welcoming everything felt. Would absolutely stay here again!

4.95 out of 5 average rating, 58 reviews

A contemporary exterior view of a charming building featuring a dark roof and light-colored walls. Four Adirondack chairs are arranged around a fire pit situated on a gravel area, set against a backdrop of lush greenery and a cloudy sky.

Home in Lawrenceburg

Bourbon Crossing II

ChristineRating, 5 stars1 day ago

What a wonderful, cozy place! My husband and I and our dog stayed at Brads place for 2 nights as we were traveling through and spending some time on the Bourbon Trail. Brad was very accommodating to allow us early check in. The house was so cute and had everything we needed, and more! The home was spotless and in a great location to explore the surrounding area.

5 out of 5 average rating, 15 reviews

A wooden swing hangs from a large tree, offering a serene spot for relaxation. The swing faces a lush green landscape, complete with rolling hills and a clear sky. A winding brick path leads toward the tree, surrounded by vibrant grass.

Farm stay in Shelbyville

Charming Bourbon Country Retreat on Beautiful Farm

Dina NicholeRating, 5 stars7 months ago

Chickapoo Farm is a hidden Gem in Kentucky! My mother, myself, and my two daughters had a wonderful stay at The Horse and The Hound. The views of the sunrise and sunset were perfect. The home is right next to the flower farm. We loved seeing all the flowers. There are great trails to walk on, delicious grass fed beef for purchase, a stocked pond for fishing, and the option to pick your own flower arrangement. The hosts were unbelievably kind and quick to respond to any questions and concerns. We will definitely be planning another visit.

4.97 out of 5 average rating, 33 reviews

oasis 522

DaveRating, 5 stars2 days ago

An absolute gem of a place right in the heart of Shelbyville. Lovely walk around town and a great Mexican restaurant right at your back door. An absolute highlight was the large vinyl collection and sound system that allowed you to play on the upstairs or downstairs speakers - amazing! Lewis also left a guitar which we enjoyed having a jam on while we stayed. The places looked even better in person than the photos and was very spacious. A wonderful stay in a beautiful small town with a lot of character

Superhost

An outdoor space is presented with a circular fire pit area surrounded by multiple Adirondack chairs. A gazebo with string lights is visible above, and a hot tub can be seen in the background. The yard is surrounded by green grass, creating a relaxed atmosphere.

Home in Versailles

5 out of 5 average rating, 4 reviews

Luxe Bourbon Trl~Game Rm~Golf Sim~Hot Tub~Fire Pit

WilliamRating, 5 stars1 week ago

Absolutely wonderful stay, easy to town, property is exquisitely done. Awesome touches!! Loved the hot tub! Game room is phenomenal. Property had wildlife daily to photograph with deer, squirrels, and birds.

A bright bathroom features a white pedestal sink and a toilet, with neatly stacked gray towels placed on top. The shower area is enclosed by a floral-patterned curtain, and a textured bath mat sits on the floor. A small mirror is mounted above the sink.

4.93 out of 5 average rating, 14 reviews

Shelbyville, KY - Bourbon Trail and Horse Country.

KerstinRating, 5 stars2 weeks ago

We enjoyed the spacious home with plenty of indoor and outdoor space to relax. The linens, bathrooms, and kitchen were very clean. We appreciated that the home is pet friendly and it was easy to walk our small dogs around the neighborhood. Angus was very responsive to our booking and request. We would stay here again and conveniently located near Shelbyville Country Club.