House holiday rentals in Shelby County

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Top-rated house rentals in Shelby County

Guests agree: These houses are highly rated for location, cleanliness and more.

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Top Guest favourite

Home in Shelbyville

5.0 out of 5 average rating, 22 reviews

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!

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Guest favourite

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, 189 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.

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Top Guest favourite

The exterior of a single-story brick house is shown under a clear blue sky. A driveway leads to a two-car garage, and a landscaped front yard features green grass and shrubs. A large window above the entrance highlights the architectural design.

Home in Shelbyville

4.97 out of 5 average rating, 64 reviews

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!

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Top Guest favourite

An inviting historic home with a vibrant blue exterior is showcased against a clear sky. The front door, adorned with multiple panes of glass, complements the white trim and large windows. Lush greenery surrounds the entrance, enhancing the charm of this property.

Home in Shelbyville

5.0 out of 5 average rating, 64 reviews

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

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Top Guest favourite

Home in Waddy

4.96 out of 5 average rating, 28 reviews

The Ridge: 6BR • 100" TV • Hot Tub • Speakeasy

Cat Ridge Resort is a modern, professionally designed private retreat in the heart of Kentucky bourbon country, perfect for unforgettable group getaways. Explore iconic distilleries by day, then return to luxury amenities and warm Southern hospitality—from a private speakeasy and relaxing wellness spaces to games, a firepit, outdoor lounges, chipping green, and more. 🥃 5 top distilleries within 25 minutes ✈️ Conveniently located between LEX & SDF 📍 Shelbyville & Lawrenceburg w/in 25 minutes

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Top Guest favourite

A light-filled living area features warm wood flooring and a decorative area rug. A cozy seating arrangement is centered around a coffee table, with a fireplace made of exposed brick as a focal point. Natural light streams through the windows, illuminating the inviting space.

Home in Pleasureville

5.0 out of 5 average rating, 29 reviews

Bourbon Trail Country Getaway

Escape to the peaceful countryside and unwind in our restored farmhouse surrounded by rolling farmland. This secluded retreat with three gas fireplaces is ideal for romantic getaways, bourbon enthusiasts, or family-friendly stays. Whether you’re sipping morning coffee on the porch, gathering around the firepit, enjoying some friendly competition in the game barn, or exploring the nearby Bulleit Bourbon Distillery on the Bourbon Trail, you’ll find tranquility and adventure in equal measure.

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Guest favourite

A bright living area features two white sofas, accented with colorful throw pillows. A rustic wooden coffee table sits centrally, displaying drinks. Two plaid armchairs are positioned across from the sofa, and vibrant artwork of cows adorns the wall, enhancing the inviting decor.

Home in Shelbyville

5.0 out of 5 average rating, 12 reviews

Hitching Post on the Bourbon Trl

The Hitching Post on the Bourbon Trail – Spacious Shelbyville retreat near charming downtown & walkable to the famous Horse Show. Minutes from Louisville & centrally located to top distilleries. Enjoy a man cave with poker, darts, shuffleboard & big screen TV, plus a screened porch for coffee or bourbon. Kids will love the playhouse over a stream in a fenced yard. Located in a safe, scenic community in the Saddlebred Capital of the World—your perfect base for bourbon & horse country!

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Top Guest favourite

Home in Shelbyville

5.0 out of 5 average rating, 15 reviews

High Rollers' Retreat w/pool and Pond

Experience an unforgettable stay at our exquisite 8BR, 8BA Speakeasy retreat, nestled in 14 acres of private, fenced-off tranquility. This adult-only haven for 16 guests, is accentuated by a dark academia aesthetic, our property channels a masculine, speakeasy vibe, peppering your stay with an irresistible dash of intrigue and sophistication. Take a moment to unwind, pour a glass of your preferred bourbon or wine and disconnect from the world. Your euphoric getaway starts here.

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Superhost

A spacious cabin is set within a landscaped area, surrounded by neatly trimmed bushes and tall trees. Morning light casts a soft glow over the scene, enhancing the natural beauty of the surrounding greenery.

Home in Finchville

4.92 out of 5 average rating, 132 reviews

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.

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Top Guest favourite

Home in Shelbyville

5.0 out of 5 average rating, 31 reviews

Jeptha Crest-Bourbon Trail, Hot Tub, Sauna, Dog OK

Jeptha Crest is a designer-built and thoughtfully decorated home, perfectly placed in the heart of the Bourbon Trail yet hidden among trees and nature views. Though centrally located, it feels like a private forest escape, offering rare privacy and calm. A spacious two-level deck, fire pit, hot tub, and sauna invite you outdoors, while inside, clean modern design blends seamlessly with warm, cozy comfort — a refined retreat created for slowing down and truly unwinding.

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Guest favourite

An open-plan kitchen and living area features modern appliances, including a sleek stove under a black hood. A round wooden dining table is surrounded by four upholstered chairs. A green couch is positioned near a textured area rug, with natural light illuminating the space through large windows.

Home in Shelbyville

4.89 out of 5 average rating, 79 reviews

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!

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Top Guest favourite

Home in Bagdad

4.98 out of 5 average rating, 159 reviews

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!

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