House vacation rentals in Shelby County

The exterior of The BarrelWoods showcases a modern farmhouse design with white board-and-batten siding and black trim. Large windows invite natural light, while decorative shutters add character. The lush green lawn is complemented by landscaping, creating a welcoming atmosphere against a clear blue sky.

5 out of 5 average rating, 46 reviews

Bourbon Trail*Hot Tub*Sauna*Mini Golf*WiFi*EVSE

Welcome to The BarrelWoods, the perfect retreat in the heart of the Bourbon Trail. This newly built home blends modern luxury with rustic charm, featuring designer touches throughout.Relax by the outdoor firepit, soak in the hot tub, or rejuvenate in the barrel sauna.Enjoy mini golf, archery, disc golf, and a game room with air hockey, shuffleboard, and more.Ideally located near iconic distilleries, fine dining, and scenic parks, The BarrelWoods is the ultimate base for an unforgettable getaway.

4.98 out of 5 average rating, 162 reviews

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

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.

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.

5 out of 5 average rating, 48 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

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.

5 out of 5 average rating, 33 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!

A charming single-level home is presented with a welcoming front porch featuring rocking chairs. Lush grass and neat landscaping frame the stone pathway leading to the front door. Trees provide shade, creating a serene setting in a quiet neighborhood.

5 out of 5 average rating, 52 reviews

Brown Ave Bourbon Trail & Beds- Shelbyville, KY

Welcome to Brown Avenue Bourbon and Beds, a beautifully renovated 1950's charmer on the Bourbon Trail, near the Shelby County Fairgrounds & just minutes from downtown Shelbyville. Start your day w/ coffee on the front porch swing, enjoy an afternoon snack on the back deck, cook dinner in the fully stocked kitchen & cozy up in the living room for movie night after a long day of exploring! A short drive to Louisville, Lexington, Frankfort, KY Derby and PGA Championship 2024 @ Valhalla! Sleeps 6

4.92 out of 5 average rating, 121 reviews

A charming cabin exterior is featured, showcasing a stone chimney and wooden deck. The deck is surrounded by a low wooden fence, and birds are seen flying overhead against a serene backdrop of trees and grassy areas.

Home in Finchville

Thoroughbred Horse Farm Cabin-located on Lamb Lake

Beautiful cabin located on a working horse farm just miles from Louisville, Frankfort and Lexington! Take in the farm scenery from our porch bed swing, or large patio with fire pit. Play a round of Air hockey, foosball, basketball shootout, corn hole, or bucket golf during your stay! Several Bourbon Distilleries are within a 30 minute drive of the property. The Cabin is 4 miles from the Outlet Shoppes of the Bluegrass, 15 miles from Taylorsville Lake, and 13 miles from Valhalla Golf Course.

A spacious outdoor patio features a round table surrounded by two sturdy, high-backed chairs. The setting is complemented by a vibrant green tree and expansive views of the surrounding countryside, providing a serene space for relaxation.

5 out of 5 average rating, 15 reviews

The Country Pleasure Farm

Welcome to our 50 acre countryside retreat, where rustic charm meets modern comfort. Our spacious 3-bed, 3-bath home offers a cozy living area, a fully equipped kitchen, and stunning views of the surrounding countryside. Conveniently located near town, the Bourbon Trail, Golf Courses, Race Tracks, and Gallrein Farms, it's the perfect getaway for relaxation and adventure. We're a working farm so expect to see tractors and harvesting taking place during your stay at this quaint and cozy farm!

5 out of 5 average rating, 14 reviews

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

Bourbon Trail Country Getaway

Escape to the peaceful countryside and unwind in our beautifully restored farmhouse, nestled on a working farm and 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, or exploring the nearby Bulleit Bourbon Distillery on the Bourbon Trail, you’ll find tranquility and adventure in equal measure.

4.99 out of 5 average rating, 104 reviews

A charming single-story home features red brick and white siding, enhanced by festive bunting along the porch. Lush green grass surrounds the exterior, and large trees provide shade in the background, contributing to a tranquil rural setting.

Home in Pleasureville

Pleasureville - The name says it ALL

This location is a Pleasure! Cozy Kentucky home off the beaten path, but close to attractions. Imagine after a full day on the bourbon trail enjoying your own piece of Kentucky with a drink in your hand. Access to 25+ acres of beautiful farmland and super clean, fully stocked private home. Close to the Outlet Shoppes of the Bluegrass making it a perfect ladies weekend get away. Additional meeting/event space available in the renovated on site barn. Reminder No Pets allowed.

The spacious living room features large circular windows that provide ample natural light. Two comfortable sofas, one in a warm rust color and another in dark upholstery, are arranged around a decorative coffee table. An elegant area rug enhances the warmth, while indoor plants add a touch of greenery.

4.93 out of 5 average rating, 73 reviews

Cozy Kentucky Winter, Bourbon Trail, Location!

♡ Meet The Blue Belle: a beautifully restored 1880s cottage ON the Bourbon Trail, nestled on a peaceful block in the heart of Shelbyville. Start your day with a coffee on the back deck, make s'mores by the fire pit, cook dinner in the fully stocked kitchen, & cozy up in the living room for movie night after a long day of exploring & bourbon! A short drive to Louisville, Lexington, & Frankfort and other great areas. Comfortably sleeps 8. Perfect for families & couples!

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.

4.86 out of 5 average rating, 51 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!

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.