House holiday rentals in Shelbyville

A dining area features a round wooden table set with glassware and green accents. A striking mural of bourbon barrels lines one wall, illuminated by a modern pendant light, while a doorway leads to other spaces in the home.

5 out of 5 average rating, 107 reviews

*Long Pour: Your Luxury Downtown Bourbon Home*

Welcome to bourbon heaven. Really. 🥃 Long Pour is located in the heart of Frankfort and bourbon country, - walking distances from Buffalo Trace, downtown restaurants, bars, and historic neighborhoods. Our place is a luxury home away from home featuring two bedrooms, an iconic shower, free parking, and not to mention the bourbon features all throughout the home. No matter your reason for visiting Frankfort, this home is the perfect getaway to enjoy the best of Kentucky. Can't wait to host y'all!

4.97 out of 5 average rating, 164 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.

4.99 out of 5 average rating, 109 reviews

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

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.

The exterior of the home features a welcoming porch with rocking chairs framed by neatly trimmed hedges. A manicured lawn with shrubs enhances the inviting approach to the entrance. Surrounding trees provide a natural backdrop, contributing to the overall charm of the property.

4.94 out of 5 average rating, 197 reviews

Wilkinson's Wheated Oasis/ 1.3 Mi to Buffalo Trace

Wake up & smell the mash! Located just steps away from Buffalo Trace Distillery. Enriched with history & tradition is where you will find Wilkinson. This historic home has recently undergone renovations & no expense was spared. Guests will enjoy the walkability to Downtown Frankfort & many of the local attractions. Featuring 2 bedrooms & 2 baths, guests are able to experience life like a local with all the modern-day amenities. We are also only a 7.2-mile drive to Castle & Key Distillery.

4.97 out of 5 average rating, 703 reviews

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

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.

A spacious living area features a plush blue sofa and two vibrant yellow chairs. A flat-screen TV is positioned on a white console. Natural light filters through multiple windows, illuminating a decorative area rug placed on the warm wood flooring.

4.95 out of 5 average rating, 102 reviews

Whiskey Woods: Newly Remodeled w/ HOT TUB!

Discover Whiskey Woods in picturesque Frankfort, KY! This 3-bed, 2-bath retreat on 3.6 acres offers modern amenities. Enjoy open-concept living, a fully equipped kitchen, and outdoor dining. Explore the lush property with grill. Sleep in plush beds, including a king-sized Whiskey Suite. Stay connected with Wi-Fi, laundry, and parking. Only 1.4 miles from Castle and Key Distillery, and 4.9 miles from Woodford Reserve. Minutes from downtown attractions. Book your Frankfort getaway today!

A spacious living area features a comfortable gray sofa adorned with decorative cushions, positioned next to large windows offering expansive water views. A glass coffee table rests on tiled flooring, surrounded by light-colored decor accents. Natural light fills the space, enhancing the serene atmosphere.

4.95 out of 5 average rating, 176 reviews

The River's Edge Oasis, close to downtown

Welcome to your oasis on the water! Relax and unwind at the River's Edge. This home is about as close as you can get to paradise in Louisville Ky (also known as River City)! Perfect getaway for a romantic weekend or the best place to relax after a long day of work! Voted #1 Vacation rental in KY by Dreamy Stays!! This unique home is designer decorated and updated with all the amenities! An 8 minute drive to downtown Louisville, the oasis offers the best of both worlds. Book today!

4.95 out of 5 average rating, 221 reviews

A serene landscape showcases a gravel path winding through lush green grass, framed by wooden fences. A large tree stands prominently, with the sun rising in the background, casting a warm glow across the misty field under a softly clouded sky.

Home in Versailles

Quaint little farm house close to Keeneland/horses

Remodeled beautiful 1900s 2 story house on farm surrounded by Creek and fire pit for your convenience. LOCATION, LOCATION!!! This is the perfect example of having the country in the city! If you are wanting the true feeling of relaxation, this is for you. Amazing views, and close to many famous attractions. 5-10 minutes away... Keeneland The Kentucky Castle Bluegrass Airport Castle Hill Winery Aviation Museum Eckert Orchard also.. Restaurants, Wineries, Breweries, Bourbon Trails

A cozy living room is presented with a dark sofa facing a white-brick fireplace. Above the fireplace, a flat-screen television is mounted. Two armchairs flank the fireplace, while a small ottoman completes the seating arrangement. Light-colored drapes frame the windows, and artwork decorates the walls.

4.87 out of 5 average rating, 221 reviews

Private EAST END gem, minutes to everything!

Cozy, East End cottage just minutes from Top Golf, shopping malls, restaurants, entertainment, and other amenities. Easy access to the expressway. Home is well appointed with granite countertops, stainless appliances, hardwood floors, and more. A seasonal creek across from the house can be heard giving the impression of a cabin in the woods with privacy and seclusion, with the convenience of city living at your fingertips. There is also a beautiful park steps away from the house.

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.

A fenced backyard features a circular stone fire pit surrounded by four Adirondack chairs. A hammock hangs invitingly between two trees, with string lights softly illuminating the area. The lush grass complements the warm ambiance created as the sun sets in the background.

4.95 out of 5 average rating, 160 reviews

Lumos Stays: 65" 4K TV, memory foam, kid-friendly

Michael and Ashley (Lumos Stays) welcome you to Louisville, home of bourbon! Centrally located, minutes from the interstate, and close to downtown and the bourbon trail, this is your home base for adventure. Enjoy the 65" 4K Roku TV, fast wifi (~317mbps), green tea memory foam mattresses, modern kitchen, kid-friendly amenities… and did you see that outdoor space? Solo Stove fire pit, hammock, propane grill, and games. Enjoy the private fenced-in backyard and large driveway!

A charming two-story house features a blue exterior with stone accents and a welcoming front porch. Green grass and well-maintained landscaping frame the walkway, while blooming flowers add a touch of color. The home is situated in a peaceful neighborhood.

4.98 out of 5 average rating, 246 reviews

Blue’s Bourbon Bungalow

A bourbon lover’s paradise. Located minutes from the worlds best Bourbon distilleries and within walking distance of several dining establishments. Enjoy walking the grounds of the state capital and touring several of Kentucky’s historical museums. Centrally located between the thriving cities Lexington and Louisville, Frankfort is the perfect home base to explore everything Kentucky has to offer.

Popular amenities for house rentals in Shelbyville

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 71 reviews

Home in La Grange

Winter Escape, Hot Tub, Game Rooms, 20 min to Lou

4.91 out of 5 average rating, 55 reviews

A charming cottage is positioned on a wooded ridge, featuring a welcoming front porch. Lush landscaping includes well-maintained bushes and small shrubs. Large windows provide ample natural light. The tranquil surroundings complement the serene atmosphere of the property.

Home in Taylorsville

Bourbon Trail Lake Home w/ Hot tub & King Bed

An aerial view reveals the Kentucky Country Manor, showcasing the main house and guest house. The landscaped outdoor area features a heated in-ground pool surrounded by lounge chairs and vibrant umbrellas, with expansive green lawns and trees enhancing the tranquil setting.

5 out of 5 average rating, 33 reviews

Louisville Country Manor - Pool & Pickleball!

4.9 out of 5 average rating, 48 reviews

Hot Tub, 10 min to Bulleit

An aerial view of the rustic country home showcases a spacious outdoor area. A round above-ground pool is situated prominently among the green lawn, surrounded by wooden decking. Nearby, several tables and a picnic space are visible, inviting relaxation and gatherings in a tranquil setting.

4.99 out of 5 average rating, 83 reviews

MacAttie Acres

4.97 out of 5 average rating, 260 reviews

A spacious backyard is illuminated by string lights at dusk, featuring a hot tub and multiple seating areas around a fire pit. The well-maintained lawn and patio area create a welcoming outdoor space for relaxation and gatherings.

Home in Schnitzelburg

5 Baths• King Beds• Hot Tub • Expo & Bourbon Trail

5 out of 5 average rating, 119 reviews

A cozy living area is highlighted by a fireplace and large windows allowing natural light. A round coffee table is positioned at the center of a comfortable seating arrangement that includes a sectional sofa and armchairs. Potted plants add a touch of greenery.

Home in Prospect

Peppermint Cottage Norton Commons w Breakfast

4.88 out of 5 average rating, 125 reviews

A welcoming front porch is presented, featuring two blue rocking chairs flanking a small table. Lush green bushes and colorful plants are visible. The porch leads to a red door, surrounded by large windows that reflect natural light and the scenic surroundings.

Home in Taylorsville

Kentucky Sunrise 18- Greet the Sun As it Rises

Weekly house rentals

A new six-seater hot tub is showcased, illuminated by soft blue lights. A small platter rests on the edge, accompanied by two wine glasses. In the background, warm light spills from an inviting seating area visible through the glass doors.

4.98 out of 5 average rating, 63 reviews

Hot Tub > 3 King Beds > 7 mins to Buffalo Trace

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, 16 reviews

The Country Pleasure Farm

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, 49 reviews

Historic Downtown~Heart of Bourbon Trail

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, 36 reviews

Bourbon Trail*4BR*Dog Friendly*6beds (3king)*Patio

5 out of 5 average rating, 21 reviews

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

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

5 out of 5 average rating, 18 reviews

Home in Douglass Hills

SuperHost ~ Beautiful NEW Modern Condo w/ 75" TV

A bright and spacious living area is furnished with a large sectional sofa and two comfortable armchairs. Natural light floods in through several windows adorned with light curtains. A neutral area rug anchors the seating arrangement, creating an inviting space for relaxation.

4.91 out of 5 average rating, 79 reviews

100 Proof Hideaway

A cozy living room features a light-colored sofa set with stylish details, positioned around a central wooden coffee table. Large windows allow natural light to fill the space, while decorative mirrors and plants add visual interest to the warm, inviting atmosphere.

5 out of 5 average rating, 34 reviews

Hot Tub Fire Pit Game Room and EV Charger

Private house rentals

A charming exterior view of a two-story bungalow features blue-green siding and a welcoming front porch. American flags are displayed, while flower beds with various plants enhance the landscaped front yard. The stone walkway leads to the entrance, inviting visitors to approach the home.

4.97 out of 5 average rating, 79 reviews

The Crafty Bourbon Bungalow Apartment

5 out of 5 average rating, 74 reviews

An open-concept living area features a cozy sofa and armchair, with light-colored walls and wooden beams above. The modern kitchen, equipped with stainless steel appliances and a spacious island, is complemented by bar seating and a view of the outdoors through a window.

Home in Crestwood

Briar Creek Cottage

4.96 out of 5 average rating, 55 reviews

A spacious living area features a light brown leather sofa adorned with decorative pillows and a plush throw blanket. A marble coffee table sits in front, complemented by a round decorative vase. Soft natural light enters through a nearby window, enhancing the relaxed ambiance.

Home in Jeffersonville

Peaceful Modern Retreat • Prime Location!

A spacious great room features a large sectional sofa with soft cushions and a coffee table placed on a vibrant area rug. A wall-mounted smart TV displays a selection of apps, while a modern kitchen with bar seating is visible in the background. Ambient lighting adds warmth.

5 out of 5 average rating, 88 reviews

Bourbon Central Waterfront Luxe near Buffalo Trace

5 out of 5 average rating, 48 reviews

A calming bedroom features a spacious bed with light bedding and decorative pillows. Natural light enters through two sheer curtains, illuminating the room. A cozy armchair sits beside a bedside table with a lamp, while artwork adds a subtle touch to the decor.

Home in Jeffersontown

Louisville Private Suite

4.91 out of 5 average rating, 55 reviews

An outdoor seating area features plush, wicker couches and a wooden coffee table, situated under a covered deck. A hot tub bubbles nearby, with peaceful lake views in the background. String lights create a soft illumination, enhancing the inviting atmosphere of the space.

Home in Lawrenceburg

Lakefront. Boat Dock. Private Bar. Hot Tub

4.99 out of 5 average rating, 93 reviews

A serene sunset is captured over rolling hills, where the sun casts warm orange and yellow tones across the sky. Wispy clouds are visible, enhancing the natural beauty of the horizon. The foreground features lush greenery, creating a peaceful ambiance.

Home in Floyds Knobs

Home with Breathtaking View

An aerial view captures the scenic setting of the mid-century retreat, surrounded by vibrant autumn foliage. The layout of the neighborhood and the winding river is visible, showcasing the home's proximity to both natural beauty and urban areas.