House vacation rentals in Shelby County

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Top-rated house rentals in Shelby County

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Top guest favorite

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.

Home in Shelbyville

5 out of 5 average rating, 29 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.

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

4.98 out of 5 average rating, 146 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

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 out of 5 average rating, 38 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

Guest favorite

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

5 out of 5 average rating, 20 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!

Superhost

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

4.91 out of 5 average rating, 116 reviews

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.

Top guest favorite

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.

Home in Shelbyville

5 out of 5 average rating, 13 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!

Guest favorite

A modern farmhouse with a welcoming façade features a spacious porch supported by dark columns. Lush green grass surrounds the home, and potted plants are placed neatly along the entryway. Large windows reflect bright natural light, creating an inviting appearance.

Home in Shelbyville

4.93 out of 5 average rating, 14 reviews

Kentucky Bourbon Trail Farmhouse-Serene Views-Pool

Come enjoy this incredible modern farmhouse and serene views, all while only being less than 10 minutes from all of Shelbyville’s amenities. We have done our best to take comfort to the next level with our memory foam beds and top of the line linens, decor, & furnishings. Start your days enjoying our bean to cup coffee overlooking the sunset rocking on the front porch, the heated saltwater pool in the afternoon, and your nights by the fire pit in the backyard enjoying the beautiful views.

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, 13 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 single-story home with a welcoming front porch is surrounded by well-maintained lawns and shrubs. The structure features multiple windows and a gabled roof, with warm evening light illuminating the exterior. A paved path leads to the entrance, enhancing accessibility.

Home in Simpsonville

5 out of 5 average rating, 14 reviews

The Haven Simpsonville* Bourbon Trail* 3 bed/3bath

Welcome to the Haven in the heart of Simpsonville, KY, the Saddlebred capital of the world. Located within walking distant of local eateries, shopping, & coffee. The Haven is close to local Distilleries, centrally located between Louisville and Lexington, on the Bourbon Trail, and less than 2 miles from The Outlet Shoppes of the Bluegrass. This spacious 3 bedroom, 3 bath home was designed to be a place of peace & comfort and is perfect for both families and group trips alike.

Superhost

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

4.82 out of 5 average rating, 34 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!

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, 32 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.

Superhost

An aerial view captures a spacious property surrounded by lush greenery. A large pool is situated in the backyard, with a fenced area visible. The home, featuring a combination of roof styles, is nestled in a semi-rural setting with nearby residential structures.

Home in Shelbyville

4.7 out of 5 average rating, 61 reviews

Pool*HOT TUB*Bourbon Trail

Are you looking for location? Look no further! This stunning home has everything your group could want! Centrally located with easy access to Louisville, Frankfort, Lexington, & so much more! In the summer the pool will be refreshing & all year long the hot tub will serve as a treat after a long day exploring! Let's not forget about the incredible game room with shuffleboard and pool table!