House holiday rentals in Shelbyville

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Top-rated house rentals in Shelbyville

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

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Top guest favourite
The exterior of Deerview Cabin features a wooden porch with a welcome sign, surrounded by hanging plants and potted greenery. A rustic metal roof contrasts with the natural wood siding. Chairs are placed on the porch, inviting relaxation in a serene rural setting.
Home in La Grange
5 out of 5 average rating, 257 reviews

Romantic country getaway with hot tub

This cabin is a completely renovated 1940's farm house 10 minutes from historic downtown LaGrange. Guests have the entire home with front and back porch overlooking the big backyard. The master bedroom has a queen bed and the second bedroom has a full bed. The kitchen is fully equipped and ready for some country cooking. The fire pit is located in the back yard ready for you or you can use the gas fire pit just steps from the hot tub. The hot tub is ready for guests with a view of stars!

Guest favourite
Home in Germantown
4.9 out of 5 average rating, 172 reviews

Bourbon Trail Spacious Backyard NEW HotTub Grill!

The Burnt Barrel, discover your vibrant Louisville getaway! Perfect for couples, business travelers, or event visitors, this cozy home offers high-speed Wi-Fi and a dedicated workspace, fully equipped kitchen, and a NEW hot tub and grill for you to enjoy! Guests rave about its comfort, walkable location, and modern amenities. Enjoy nearby bars and restaurants all just minutes from downtown, UofL Health, and the Convention Center. Experience true Louisville charm and convenience! Book a stay now!

Guest favourite
The exterior of the remodeled house is framed by lush trees, showcasing a welcoming deck with ambient lighting. A traditional barrel sauna is positioned nearby, blending with the natural surroundings. The inviting façade reflects warm tones, enhanced by the soft glow of the setting sun.
Home in Frankfort
4.99 out of 5 average rating, 107 reviews

Bourbon Trail*River Views*Hot Tub*Sauna*EVSE*WiFi

Welcome to River Whisper. The remodeled riverfront house offers the perfect blend of organic modern decor and unparalleled comfort. Experience luxury with top-of-the-line features, a hot tub, and a barrel sauna, all overlooking the beautiful Kentucky River. Located in the heart of Bourbon Trail, with easy access to many renowned distilleries, including Buffalo Trace and Woodford Reserve. Explore historic downtown Frankfort, Cove Spring Park, river boat tours, kayaking, fishing, hiking and more.

Top 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, 166 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 favourite
The exterior of a brick home is shown, featuring a welcoming front door in a light teal shade. Surrounding landscaping includes neatly trimmed shrubs and flowering plants, with a concrete pathway leading to the entrance. A well-maintained lawn stretches out in front.
Home in Frankfort
4.99 out of 5 average rating, 105 reviews

Backyard Bourbon Retreat

Your family will be close to everything when you stay at this centrally-located place. This is a beautiful two bedroom two full bath home packed with a ton of amenities! Only minutes from several distilleries such as Buffalo Trace, Jim Beam, Woodford Reserve, Ancient Age and Four Roses just to name a few! There is a fully fenced in yard with a deck looking into a 1/4 acre landscaped backyard. Great for sitting back and relaxing with a Kentucky beverage. Welcome to the Backyard Bourbon Retreat!

Guest favourite
A welcoming exterior view of a stylish house features a covered front porch with seating and decorative elements. The spacious interior showcases a cozy living area with comfortable seating and art on the walls. A well-maintained outdoor space includes a putting green. Natural light brightens the rooms.
Home in Jeffersonville
4.99 out of 5 average rating, 123 reviews

Walking Bridge, Putt Putt House

NEW LISTING: Welcome to our walking bridge home on Pearl St. We have a hot tub, putt putt, and all the fun you can think of in one home. Steps away from restaurants, shopping, and bars, as well as the walking bridge to Louisville. This home is closer to the fun in Louisville than most neighborhoods in Louisville itself. Go out or stay in, you're guaranteed to have a great time in this newly renovated gem. We have high quality mattresses, and smart TV's in both bedrooms and the living room.

Guest favourite
Home in Finchville
4.92 out of 5 average rating, 125 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.

Guest favourite
A welcoming view of The Spencer cottage is presented, showcasing lush greenery and carefully tended landscaping. A sign is positioned in the foreground, displaying the name of the property. The brick exterior of the cottage is framed by trees, enhancing its charming appeal.
Home in Frankfort
4.9 out of 5 average rating, 132 reviews

Frankfort’s Capitol view cottage

Frankfort's Capitol View Cottage Named for architect Spencer Cryer, the Spencer offers a unique charm with the comforts of home on your central Kentucky travels. An off the beaten path yet still downtown cottage with a seasonal view of the Capitol, the home offers both inside and outside amenities. Steps from the Capitol grounds and 20 miles to Lexington 50 miles to Louisville and within an hour drive of at least 10 distilleries on the Bourbon Trail including Buffalo Trace a local favorite!

Top guest favourite
The entrance to the historic Buffalo Springs Distilling Company is showcased, featuring sturdy stonework and a wooden door. A sign hangs above the entrance, indicating the building's name. Nearby, green grass is visible, hinting at the surrounding area.
Home in Stamping Ground
4.97 out of 5 average rating, 712 reviews

Buffalo Springs Distilling Company

It’s recently been brought to our attention about Airbnb scams! Please reserve with us or someone else that has a history! The Bourbon Trail The Buffalo Springs Distilling Company got it's start in 1868. It closed and it's warehouses were emptied out by the 1970's. This building is one of the last structures left on the site. This historic building was the main office and gatehouse for visitors to the distillery, so we can offer one Queen sized bedroom due to the size of the structure.

Top guest favourite
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
4.99 out of 5 average rating, 105 reviews

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.

Top guest favourite
A bright living area features a comfortable gray sofa adorned with colorful throw pillows. A round coffee table sits atop a soft area rug, complemented by wooden chairs nearby. Natural light streams through multiple windows, creating a welcoming atmosphere in this open space.
Home in Frankfort
4.99 out of 5 average rating, 185 reviews

Limestone Landing - Cozy Luxury Retreat w/ HOT TUB

Limestone Landing is a modern, peaceful home, thoughtfully designed with comfort and style in mind. This cozy haven offers a relaxing place to unwind after a day of exploring bourbon country. Just minutes from Castle and Key and Woodford Reserve and only ½ mile from the highly rated restaurant and bourbon bar, The Stave. Whether you’re here for tastings, scenic drives, or quiet evenings in, Limestone Landing puts you right where you want to be!

Guest favourite
The exterior of the home features a light beige facade with a metal roof and a vibrant red front door. Two shrubs frame the entrance, and the porch is accessed by three steps, providing a welcoming approach. Clear skies and lush greenery enhance the setting.
Home in Middletown
4.93 out of 5 average rating, 156 reviews

HOUSE ON HERRICK

Fully renovated home in the heart of Historic Middletown. Hardwood and tile floors throughout. Queen size memory foam mattresses in both bedrooms and a full-size blowup mattress can be used in the living room if needed. 3 blocks from Main Street where you will find restaurants, shopping, and antiques! 15 minutes from Churchill Downs! Less than 1 mile to Interstate 64 with a quick Uber ride to downtown, Crescent Hill, and the Highlands.

Popular amenities for house rentals in Shelbyville

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Quick stats about house rentals in Shelbyville

  • Total holiday rentals

    Explore 30 holiday rentals in Shelbyville

  • Nightly prices starting at

    Shelbyville holiday rentals start at £60 per night before taxes and fees

  • Verified guest reviews

    Over 1,040 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Shelbyville holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Shelbyville rentals

  • 4.9 Average rating

    Shelbyville stays are highly rated by guests – averaging 4.9 out of 5!

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