Vacation rentals in Shelby County

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Top-rated vacation rentals in Shelby County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

A wooden sign reading 'Cottage on Crooked Creek' is prominently displayed, featuring an artful depiction of deer near a cottage by a creek surrounded by trees. Soft greenery and natural scenery provide a serene backdrop, enhancing the connection to nature.

Home in Lawrenceburg

4.98 out of 5 average rating, 142 reviews

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.

Top guest favorite

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.

Guest suite in Shelbyville

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.

Top guest favorite

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

4.91 out of 5 average rating, 123 reviews

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!

Guest favorite

A turquoise Keurig coffee maker is displayed next to a white mug featuring a butterfly and flower design. A carousel holds various coffee pods, showcasing diverse brands and flavors. The coffee station is situated on a light-colored countertop with a modern tile backsplash.

Home in Shelbyville

5 out of 5 average rating, 11 reviews

WelcomeTreatsWaiting| CentralLocation| Comfortable

Cozy 750 sqft home designed for convenience and comfort 1 bdrm w/ comfy queen bed, 1 bath and a pull out couch Stocked w/ snacks, toiletries, and coffee & tea options Outside enjoy the fire pit (wood provided) or fire up the grill for a burgers or steak Located across from the fairgrounds in safe, charming downtown Shelbyville, you'll have easy access to local events, dining, and shopping Whether you're here to explore the Bourbon Trail or just unwind this spot offers everything

Guest favorite

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.

Guesthouse in Shelbyville

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.

Top guest favorite

A well-appointed kitchen features dark wooden cabinetry and modern stainless steel appliances. Natural light filters through large windows, illuminating the white countertops. Exposed brick accents impart a rustic charm, while elegant details are found in the coffered ceiling and wood paneling along the walls.

Loft in Shelbyville

5 out of 5 average rating, 24 reviews

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.

Guest favorite

Loft in Shelbyville

4.98 out of 5 average rating, 106 reviews

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

Top guest favorite

Cabin in Lawrenceburg

4.99 out of 5 average rating, 85 reviews

Hidden View Cabin

Welcome to Hidden View Cabin, a delightful cabin where seeing wildlife and listening to the sounds of nature are yours to enjoy! Take the scenic drive down the gravel lane to this private and peaceful place located among pine trees and overlooking a one acre pond. Whether you have come to relax and get away from it all or want to visit the many attractions throughout central Kentucky this is the place for you. Only 20 minutes from Lawrenceburg.

Top guest favorite

Home in Shelbyville

5 out of 5 average rating, 29 reviews

The Back 40 ~ Modern*Bourbon*Scenic*Private

The Back 40...where rural charm meets the modern amenities you expect. Overlooking the Jeptha Creek and situated in a serene Kentucky cattle pasture, this piece of country gold is your gateway to Kentucky's lauded Bourbon Trail and the Saddlebred Capital of the World. The Back 40 is perfect for Bourbon Trail adventurers, those seeking a little retail therapy, or folks simply aiming to escape to a slower pace of life for just a spell.

Top guest favorite

A circular seating area features six Adirondack chairs arranged around a stone fire pit. The surrounding grassy space is dotted with trees, with a vibrant sunset illuminating the sky in the background.

Home in Finchville

5 out of 5 average rating, 40 reviews

Country Retreat on Bourbon Trail - Fire Pit - King

Surrounded by farmland, but close to Louisville, Frankfort, distilleries, and shopping! Start your morning on the front porch with a cup of coffee or tea and watch the horses across the way. Hop over to Louisville for the day, and afterwards, your tranquil country oasis awaits! Grill out and chill by the fire pit. Do some star gazing. Or just enjoy the peace of Kentucky’s countryside.

Guest favorite

The exterior of the home features a welcoming front porch supported by white pillars. Lush green bushes frame the entrance, while red flowers add a touch of color to the landscaping. Light blue accents are visible near the door, set against a clear sky.

Home in Simpsonville

4.87 out of 5 average rating, 152 reviews

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.

Top guest favorite

A bright studio space features exposed brick walls and large windows that allow ample natural light. Modern furniture includes a red bed and two vibrant seating areas in green and blue. A minimalistic dining table is positioned near the seating, creating an open and inviting atmosphere.

Loft in Shelbyville

5 out of 5 average rating, 21 reviews

Ideal Location + Futuristic Decor | Galaxy Getaway

Welcome to Galaxy Getaway! This cosmic-themed studio on 6th Street in Shelbyville, KY, offers unique, out-of-this-world amenities for an unforgettable getaway. Whether you’re here to relax or embark on an adventure, your galactic escape starts here! 📍Prime Location 👾 Variety of fun games 🚀 Out of this world decor ✨ Modern amenities