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

The exterior of a modern cottage is displayed, featuring a gray wood-paneled facade, a sloped roof, and a welcoming front entrance. A wooden staircase leads up to the porch, where inviting seating arrangements can be seen. Lush greenery surrounds the home, enhancing the tranquil setting.

Home in Lawrenceburg

4.97 out of 5 average rating, 152 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.

Guest favorite

A spacious living area is showcased with a large sectional couch in brown leather, complemented by decorative cushions. A round, patterned coffee table sits in front, while soft light filters through the window blinds, providing a cozy ambiance. Wall artwork adds character to the room.

Guest suite in Shelbyville

4.94 out of 5 average rating, 17 reviews

Bourbon& Beyond ready! Bourbon trail close by.

Welcome to Kentucky! We have the perfect newly renovated guest suite for visitors whether you are headed to our famous Kentucky Derby, Bourbon Trail tours, or more. You will have your private entrance, a comfortable living area, a fully stocked kitchenette, a full bath, one bedroom with a queen bed, and a living room with a large sectional couch and TV. WiFi is available, and we are a short drive to Frankfort, Louisville, and Bardstown. #distillerytours#bourbon #bourbontrail #derby#railfest

Top guest favorite

A charming exterior features a house with large windows and red front doors, set against a backdrop of colorful autumn foliage. The ground is blanketed with fallen leaves, and sunlight casts long shadows across the landscaped area, providing a serene atmosphere.

Guest suite in Shelbyville

5 out of 5 average rating, 99 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

An aerial view showcases a spacious estate with bright outdoor lighting highlighting the landscaped grounds. A recreational area featuring basketball courts and seating is visible, offering ample space for outdoor activities, while the elegant façade of the home provides an inviting presence.

Home in Shelbyville

5 out of 5 average rating, 16 reviews

Speakeasy|Hot Tub|Theater|Pickle Ball|Sleeps 20

Experience luxury at Oak & Ember Estate—an elegant 8-bedroom retreat (20 guest maximum) in the heart of bourbon country. This estate is situated on 5 private acres featuring designer rooms, private theater, hidden speakeasy, hot tub, and dual living spaces. Perfect for bourbon enthusiasts, families, and discerning travelers. Ideal location for distillery tours with exceptional entertainment spaces and thoughtful luxury touches throughout. Your unforgettable Kentucky experience awaits!

Guest favorite

A restored farmhouse is shown with a charming white exterior and a black roof. The front porch features white railings, while the surrounding lawn is well-maintained with a grassy area and some trees in the background.

Chalet in Lawrenceburg

4.96 out of 5 average rating, 211 reviews

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.

Top guest favorite

The exterior of the home presents a charming facade with white siding and brown shutters framing two windows. A green door welcomes guests, flanked by small evergreen shrubs. Stone steps lead to the entrance, surrounded by seasonal foliage.

Home in Shelbyville

5 out of 5 average rating, 15 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

Top guest favorite

A comfortable living area features a neutral-colored sofa and a wooden coffee table. A ceiling fan hangs above, while a television is mounted on the wall above a decorative fireplace. Natural light enters through two windows, complemented by rustic wall accents.

Guesthouse in Shelbyville

4.97 out of 5 average rating, 117 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.

Guest favorite

The spacious living area features large windows allowing ample natural light. Elegant details include high ceilings and exposed brick walls. A plush sofa is arranged around a coffee table, while a dining area with a wooden table is visible in the background.

Loft in Shelbyville

4.87 out of 5 average rating, 30 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

The open-concept living area features exposed brick walls and wooden beams, creating a blend of historical charm and modern design. A plush sectional sofa is positioned near a wall-mounted television, with a dining table set for six nearby. Large windows provide views of Main Street.

Loft in Shelbyville

4.98 out of 5 average rating, 107 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

Condo in Shelbyville

4.94 out of 5 average rating, 142 reviews

Work, Play or Bourbon $99 nights thru 8/31

2-bedroom, 2 full bathroom condo offers a one level floor plan and a private entrance with parking at your door. Just a few minutes to Bulleit Distillery, you will be located in the center of the Bourbon Trail. Here for work? Grocery, shopping, interstate are within a few minutes. In town for a festival? Let us help you plan with local recommendations and hidden gems! All the essentials are provided and a few extra special touches too.

Top guest favorite

A modern rural structure is showcased with a spacious wooden deck that extends across the front. String lights are suspended above, adding a soft glow. The surrounding landscape features a grassy area and a black wooden fence, with trees in the background.

Home in Shelbyville

5 out of 5 average rating, 36 reviews

The Back 40 ~ Modern*Scenic*Private*EV Charging

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, 48 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.