Accommodations in Shepherdsville

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.

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.

A fully-equipped kitchen is presented with modern appliances, including a stainless steel refrigerator and dishwasher. Light wood cabinets complement the countertop, while overhead lighting enhances the workspace. An archway leads to a hallway, suggesting easy access to other areas of the home.

4.95 out of 5 average rating, 186 reviews

Bardstown Bourbon Bnb - near My Old KY Home

Welcome to our charming Airbnb in Bardstown, Kentucky, the bourbon capital of the world! Situated in the heart of downtown, our spacious and beautifully decorated home is the perfect retreat for bourbon enthusiasts, history buffs, and nature lovers alike. Boasting of three comfortable bedrooms, each furnished with plush bedding. The living area is bright and airy, with large windows and comfortable seating for you to relax. The fully-equipped kitchen is perfect for cooking up delicious meals.

4.95 out of 5 average rating, 126 reviews

The exterior of the home showcases a brick facade with a well-maintained lawn. Colorful flower beds with various flowers and decorative pumpkins enhance the welcoming entrance. A car is parked in the driveway, and a bright blue sky provides a clear backdrop.

Home in Elizabethtown

Applewood Cottage Welcome Home

You'll experience all the comforts of home. A level entrance and easy access to every room. There is a walk-in shower located in the master bath, helpful for anyone with limited mobility. Bedrooms are separated, which allow privacy. Washer and dryer for your laundry needs, large kitchen fully equipped. A private, covered outdoor space provided with a grill and propane heat that allows extra room for dining. Minutes to all attractions. 1m music festival 15m Blue Oval 20m Fort Knox 8 m Ball Park

A visitor guide to Bourbon Country is displayed on a rustic surface. The cover features a classic car adorned with a large barrel, set against a scenic backdrop of rolling hills and quaint buildings. The title is prominently emphasized in gold lettering.

4.88 out of 5 average rating, 287 reviews

Bardstown Bourbon Trail House ❤️

Bourbon trail getaway in historic downtown Bardstown. Enjoy this entire home during your stay in the "Most Beautiful Small Town in America." Cottage located on a quiet side street. Walking distance to My Old Kentucky Home Dinner Train, Restaurants, Bars, Coffee and Fabulous Boutique Shops. Parking for 3 vehicles. 1 queen bed downstairs. 1 queen bed upstairs & 1 full-size bed upstairs. Brand new renovated bathroom downstairs AND renovated bathroom upstairs. Home is not handicap accessible.

4.99 out of 5 average rating, 405 reviews

The front porch is framed by two white columns and features a welcoming door adorned with a yellow wreath. Lush greenery is positioned beside the entryway, enhancing the cozy exterior with a wooden floor and natural light filtering in.

Cottage in Bardstown

The Cottage Circa 1898 Downtown Location

Charming 1800's cottage listed on the National Register of Historic Places in Bardstown. Voted Most Beautiful Small Town in America. Walking distance from downtown shopping, nightlife, dining, and local attractions. Located along the Kentucky Bourbon Trail. I love Bardstown and wanted my cottage to look and feel like what is best about the town- historical charm mixed with modern amenities. Clean, cozy and comfortable; it is a space that I hope you find enjoyable while visiting Bardstown.

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, 295 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.

4.92 out of 5 average rating, 106 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.

5 out of 5 average rating, 120 reviews

An open living area is characterized by exposed brick walls and wooden ceiling beams. A modern kitchen with high stools faces a spacious island, while a large screen TV is mounted on a feature wall. A colorful area rug adds warmth to the seating area.

Loft in Lebanon

Sunny Side Up

Sunny Side Up is situated on the second floor of the Sunny Side Saloon, a historic building with a rich past. Originally serving as a Union Army Commissary during the Civil War, it later transformed into a cherished local establishment known as the Sunny Side Saloon. Here, JH Kearns once sold his own pre-prohibition whisky, often packaged in ceramic jugs. Located in downtown Lebanon, in the heart of Kentucky, Sunny Side stands proudly on the historic Bourbon Trail.

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What guests are saying

Derby House with Hot tub and King Bed

5 out of 5 average rating, 10 reviews1 month ago

We really enjoyed our time here. It’s very convenient to all the Louisville attractions. Check and process was very easy and the house was very clean. There were great restaurants nearby. In a very friendly neighborhood. Johlandi was very responsive, she is an excellent host.

Home in Louisville

What guests are saying

The Full Proof Penthouse (Bourbon Trail)

5 out of 5 average rating, 32 reviews1 week ago

We absolutely loved our stay in Bardstown and wish all our Airbnb's were on this level. The penthouse is so easy to get to and spacious. It's right near everything, which makes exploring so easy. The decor is fabulous and it's just a great place. If you are on the fence, book this - you won't regret it!

Apartment in Bardstown

What guests are saying

Historic Nulu Loft| Downtown | Bourbon Trail

4.93 out of 5 average rating, 90 reviewstoday

Great stay!! The hosts were very responsive and helpful. It was a great area to get to fun places in Nulu and super convenient to walk to Whiskey Row. Big city with a small town feel and felt very safe where we were. The back courtyard was a cute area to privately relax outside ! I ❤️Louisville!!!

Loft in Central Business District

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

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Popular amenities for Shepherdsville accommodations

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Other great vacation rentals in Shepherdsville

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

4.94 out of 5 average rating, 66 reviews

Home in Shelbyville

B on the Bourbon Trail with pub, pool and hot tub

5 out of 5 average rating, 11 reviews

An outdoor living area features a comfortable green sectional sofa positioned around a wooden coffee table. A wall-mounted TV is visible, and ceiling fans are installed for airflow. Large windows allow for natural views of the surrounding greenery.

Home in Elizabethtown

Large Home with Entertainment Options Galore

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