Places to stay in Shelbyville

4.91 out of 5 average rating, 207 reviews

The view from the loft features a charming street scene in downtown Bardstown. Two cars are parked along the road, with storefronts visible on either side, showcasing varied architectural styles. Trees line the sidewalk, adding greenery to the bustling atmosphere.

Apartment in Bardstown

Historic Loft in the ❤️️ of Bardstown

Stay in the heart of downtown Bardstown, named one of "the most beautiful small towns in America". Just out your door are numerous restaurants, shops, family activities and nightlife. Located on the Bourbon Trail, you will be a short drive from several popular distilleries. Our loft is perfect for a Bourbon Trail explorer, a couples getaway, families and business travelers. You will also find popular local events such as the Kentucky Bourbon Festival and Arts and Crafts Fair just steps away.

4.83 out of 5 average rating, 126 reviews

A welcoming entrance is highlighted by a set of stone steps leading to a covered porch. Vibrant flowers enhance the greenery, while elegant architectural details are seen on the house. The porch features a decorative railing and a couple of seating areas for relaxation.

Apartment in Louisville

Highlands Harmony House - Near Cherokee Park

Upstairs; full sized Studio Apartment with large bedroom, kitchen, separated bath, private, big screened porch! The PRIVATE bathrooms are in the hall -3 feet from your bedroom/hidden behind privacy screens. "Yes, you can run to the bathroom in your 'all-together!" You'll love the kitchen and comfortable queen bed. Very cozy! Private screened porch overlooks our artistic/wooded backyard! Located on a quiet dead end street. Stroll our shady sidewalks to local bars coffee shops, restaurants etc.

Guest suite in Louisville

A modern entrance is showcased with a sleek black door featuring decorative panels. Lush greenery and blooming hydrangeas frame the stone pathway, which leads towards the door. Subtle outdoor lighting enhances the welcoming atmosphere as the pathway is bordered by neatly arranged stones.

4.97 out of 5 average rating, 136 reviews

Action City! Extravaganza at Bardstown Rd!

In the HEART of the Highlands, this spot sits near the corner of the main strip- just steps to Bardstown Rd. A few minutes drive to anywhere in city limits! And exactly where YOU want to be! Action Packed: Restaurants, Shopping, Bars, Parks, and Church- all walkable. A surprise local GIFT CARD given with each stay! This place is stylish, chic, cozy, and extremely quiet, as double pane windows have been installed. Recently renovated, it houses all the essentials for a weekend or week long stay.

4.84 out of 5 average rating, 108 reviews

A wooden deck is visible through multiple window panes, featuring several lounge chairs arranged for relaxation. Surrounding greenery offers a serene backdrop, and a glimpse of a nearby structure can be seen beyond the deck.

Bungalow in Louisville

Sweet Highlands Victorian 2Blocks off Bardstown Rd

My place is close to nightlife, public transport, parks, and the city center. You’ll love my place because of the high ceilings, the coziness, the comfy bed, the light, and the kitchen. My place is good for couples, solo adventurers, business travelers, families (with kids), and big groups. Nulu and downtown are minutes away. You can stroll down our lovely sidewalks and look at the beautiful Victorian houses and trees, enjoy some great food, with lots of quirky shops just footsteps away. Enjoy!

Superhost

A spacious living area features a circular gold leather couch surrounding a suspended fireplace. Exposed wooden beams and original brick walls enhance the character of the loft. Soft seating and decorative cushions invite relaxation, while the unique patterned wall adds visual interest.

Loft in Shelbyville

4.97 out of 5 average rating, 112 reviews

Bottled in Bond: Close to Buffalo Trace and Others

Best place to stay on the Bourbon Trail FEATURED on HGTV! Swanky! Stunning! Spectacular! You'll be in a top-floor loft overlooking downtown Shelbyville and perfectly situated in the heart of the Bourbon Trail! Incredible place to stay for Derby, Keeneland, PGA or local weddings and events---if you can pry yourself away from here! We specialize in making your stay an over-the-top experience and are happy to arrange chauffeured transportation, private chef accommodations, and dinner reservations.

A coffee maker sits on a granite countertop, featuring a digital display and multiple buttons for brewing settings. The glass carafe is positioned beside the machine, reflecting natural light from the surrounding area.

4.94 out of 5 average rating, 126 reviews

The TEB House, Walk to Downtown

Come stay in our peaceful and centrally-located home in the Most Beautiful Small Town in America. We renovated this home with guests in mind, to make it a clean and comfortable space to come and relax while visiting Bardstown! Located near Saint Joseph Proto Cathedral, you will be in walking distance of all things Downtown Bardstown. We have 3 bedrooms, a living space with basic cable and access to streaming sites, washer/dryer, renovated bathrooms and kitchen. On site parking for 2-3 vehicles.

4.9 out of 5 average rating, 146 reviews

A welcoming front porch showcases a bright, inviting entrance with a swing and potted plants. The porch is framed by tall windows and adorned with climbing greenery. Steps lead to a well-kept pathway surrounded by low shrubbery.

Home in Highlands

The Highland Fling - restaurant row, walk to all!

- ABSOLUTE BEST LOCATION!! LOUISVILLE'S RESTAURANT ROW!! - Sterilized Property - Superhost Property! - Charming house in Historic Highlands - 1 Block from Bardstown Rd - Restaurant Row - Walk to local shops and the BEST restaurants - Great backyard -1 full bath on first floor, one up -living room with sleeper sofa - Street parking for this residence - Fully stocked kitchen - 6.3 Miles to Churchill Downs - 2.8 Miles to Downtown/Convention Center - >1 Mile to Cherokee Park *NO locals*

A bustling downtown scene is captured, featuring colorful storefront signs, including 'The Cozy Cottage' and 'Artists Barrel.' The sidewalk is busy with pedestrians, and cars line the street under a clear blue sky, suggesting a lively atmosphere in Bardstown.

4.92 out of 5 average rating, 294 reviews

The Nicholson Guest House

Stay in a historic cottage, dating back to the 1830's. Conveniently located in the heart of downtown Bardstown, within walking distance to restaurants, shopping, markets, events, and nightlife. Bardstown is the Bourbon Capital of the World! Don’t hesitate to visit some local distilleries to experience some truly amazing Bourbon. Farm fresh eggs, homemade pancake mix, snacks, and water are provided to all guests. We also offer Electric Bicycles. Contact me directly for info.

4.87 out of 5 average rating, 171 reviews

A charming house features a classic facade with tall white columns and a wide staircase leading to the entrance. Large windows are framed with flowing curtains, allowing natural light to enhance the inviting atmosphere under the leafy canopy of surrounding trees.

Home in Louisville

Prime Highlands Location - 500ft fro. Midcity Mall

Formerly known as Breslin House, this well-loved Airbnb (126 five stars reviews) is under a new host. We are confident you'll love it as much as everyone did before! Our house is located on a quiet street, but steps away from restaurants, bars, boutiques, and cafes on Bardstown Rd. It's perfectly situated in the heart of the Highlands so you can walk to almost everywhere. Our home is very spacious with 3 large bedrooms, so you'll have plenty of privacy even with a large group.

4.93 out of 5 average rating, 105 reviews

The image shows a hot tub on a covered deck, with bubbling water and a view of a backyard fire pit area below. Four blue Adirondack chairs surround the fire pit, which is under a canopy of string lights amidst lush greenery.

Home in La Grange

Hot Tub-King Bed-Coffee Bar-Arcade-Fire Pit!

Centrally located in La Grange, the Kindness Capital of Kentucky. Welcome to the hallmark of small towns where the train rolls down Main Street over 30 times each day. Walk to locally owned donut and coffee shops, Farmer’s market, playground with splash pad, and restaurants. Spend your day on the Bourbon Trail or Churchill Downs before relaxing in the Hot Tub. Driving distance to the Creation Museum and Ark Encounter, The Slugger Museum, Falls of the Ohio, and Mega Caverns.

4.94 out of 5 average rating, 512 reviews

The charming exterior of the cottage is highlighted by two symmetrical windows and a central door framed with dark wood. Lush greenery properties a potted plant atop a rustic barrel and vibrant flowers adorn the window boxes, enhancing the inviting entrance.

Guesthouse in Lexington

The Bourbon House- Downtown Lex’s Premier Air B&B

Welcome to "The Bourbon House" Downtown Lexington's Premier spot to stay for an authentic Kentucky experience. This cottage was built by me from the ground up with no details spared to immerse my guests in the finest things Kentucky has to offer- Fully stocked bourbon bar mixers! (You supply bourbon) Hand crafted house and furnishing from reclaimed wood and bourbon barrels, private hot tub, bathrobes, garden, fire pit, and walking distance to downtown and Rupp arena

4.98 out of 5 average rating, 100 reviews

A modern entertainment area features a classic arcade game machine alongside a cozy seating arrangement. Dark cabinetry contrasts with lighter walls, while a decorative wall piece adds visual interest. The space is illuminated by natural light streaming in from a round window.

Home in Highlands

Highlands Lookout

Welcome to Highlands Lookout, your ultimate spot for a good time on Bardstown Road in the lively Highlands of Louisville! Perfect for guys' or girls' weekends, concerts, and conventions. Immerse yourself in the vibrant atmosphere of "Keeping It Weird." Unwind on our balcony or chill out on the lower porch. Close to distilleries, bars with rare bourbons, downtown, racetrack, and the airport. Your gateway to a thrilling Louisville adventure!

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What guests are saying

Vintage 99 bed and breakfast

4.86 out of 5 average rating, 14 reviews1 month ago

In terms of value for what you pay here, this place is a steal! Great for a quick weekend place to stay! The home is exactly as described and looks pretty much identical to the pictures. I highly recommend! The only downside is that it feels a little cramped when you have 5+ people. But, if you only intend to stay the night here and clean up after a long day, I can’t say there are any downsides at all! Great place! Host responds quickly and the place was clean.

Home in Louisville

What guests are saying

Not Everything is Black &White Rooftop Penthouse

5 out of 5 average rating, 11 reviews1 month ago

Place was beautiful! I booked this air bnb for my best friends bachelorette she really loved the place. Air bnb was walkable to a lot of restaurants, bars, shops and activities. Host was very nice,talked to us about the place and gave us a run down of everything about the place and let us enjoy it for the rest of the stay! Place was really clean and nicely decorated. One of the bathrooms had a bidet with a warming seat which was super cool! 10/10 would recommend!!

Apartment in Central Business District

What guests are saying

Kentucky Horse Farm Barndo On The Bourbon Trail

4.93 out of 5 average rating, 246 reviews3 weeks ago

3rd time we have stayed here. It is a very beautiful and peaceful place. The mornings and evenings on the deck with coffee or a drink are amazing. Alona makes this place what it is. She is very attentive and helpful, always ready to help you make your stay a memorable one.

Home in Harrodsburg

What guests are saying

1920s Highlands Gem – Kentucky Derby & Bourbon

4.79 out of 5 average rating, 39 reviews1 week ago

If I could give it six starts I would. We had a wonderful stay!!! The home was not only well decorated but inviting and great for relaxing. The neighborhood was cute and safe. The beds were comfortable and the showers were awesome. I can’t say enough nice things about this place.

Home in Louisville

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Stay near Shelbyville's top sights

Jeptha Creed Distillery36 locals recommend

Bell House Restaurant17 locals recommend

Claudia Sanders Dinner House16 locals recommend

Talon Winery Tasting Room14 locals recommend

La Cocina de Mama12 locals recommend

The Red Lion8 locals recommend

Other great vacation rentals in Shelbyville

A covered patio is illuminated by string lights, offering a cozy space with a round table and four chairs. A patterned rug enhances the area, while a grassy backyard is visible through the railing. A shed can be seen in the background.

4.97 out of 5 average rating, 33 reviews

*Sweet Southern Comfort* 3 Qn bd 2+bth sleeps 6

4.98 out of 5 average rating, 143 reviews

An outdoor patio features two black lounge chairs positioned around a small white table. A fire pit with flames adds warmth to the setting, surrounded by a grassy area and scenic views of distant trees and hills, with a colorful sky at sunset.

Cabin in Mount Eden

Bourbon Country Cottage

4.89 out of 5 average rating, 122 reviews

Cottage in Taylorsville

Best view of the lake two bed two bath cottage #4

An outdoor patio area features a round table surrounded by six mesh chairs. A grill is positioned nearby, and flower pots add greenery to the wooden deck, which overlooks a spacious lawn dotted with trees.

4.92 out of 5 average rating, 138 reviews

McIntyre’s Country Getaway

4.91 out of 5 average rating, 118 reviews

The exterior of a charming cabin is displayed, featuring a wooden facade and a metal roof. A welcoming yellow door is centered, flanked by large windows. A stone chimney rises beside the building, while a grassy area is visible in the foreground.

Home in Harrodsburg

Private Cabin on Bourbon Trail with Hot Tub

Cottage in Spencer County

Aerial view captures Taylorsville Lake, surrounded by lush greenery and autumn foliage. The winding shoreline is visible alongside the marina with several boat docks. The community road runs beside the scenic landscape, providing a clear view of the serene water and rolling hills.

4.91 out of 5 average rating, 151 reviews

Peaceful Cottage Minutes from Lake Access

Superhost

An exterior view of a modern patio area features stacked stone benches surrounding a fire pit. A black metal staircase leads to an upper level, framed by textured brick walls and lush greenery. Paved pathways extend through the outdoor space.

Apartment in Lexington

4.84 out of 5 average rating, 37 reviews

Count Fleet @ 3Forty /2BR Apt/ Walk to Rupp Arena