Holiday rentals with outdoor seating in Bardstown

A bright living area features a beige couch, complemented by a striking pink wall adorned with a bird mural. A wooden table sits atop a bold red rug, while large windows allow natural light to illuminate the space, enhancing the clean, open layout.

4.99 out of 5 average rating, 173 reviews

Historic Home with Secret Speakeasy right Downtown

The best that Bardstown has to offer! This beautiful, historic, art deco gem is right, smack dab, downtown. The coolest part? Somewhere in the house, behind a hidden bookcase door, you’ll find a secret speakeasy with a beautiful bar setup. One block from the best food, two blocks from the Museum of Whiskey History, and around the corner from all the best bars. Easily the most memorable spot in Bardstown. 10+ distilleries within 10-20 min including Heaven Hill, Bardstown Bourbon and Jim Beam.

4.98 out of 5 average rating, 251 reviews

A rustic cabin is nestled among trees, featuring a well-lit entryway and a front deck with two wooden lounge chairs. Soft evening light spills through the windows, creating a welcoming atmosphere. Stone stepping stones lead towards the doorway, enhancing the natural setting.

Cabin in Lawrenceburg

Romantic Cozy Cabin Getaway w/ Firepit & Hot Tub

Privately nestled on over 5 wooded acres & intentionally curated for your stay. Gain access to quiet, immerse yourself in nature, support your rejuvenation, & to tap into your creative flow. Amenities include on-site hiking trail, artist work space, wood burning stove, covered porch, hammocks, outdoor dining, fire pit, moon garden, salt-water hot tub, & outdoor shower. Close to Beaver Lake & located along the Bourbon Trail, just minutes from Wild Turkey & Four Roses distilleries. (Note:18+only)

4.9 out of 5 average rating, 122 reviews

An outdoor living space features a hot tub beneath a wooden pergola, with water cascading gently. Comfortable seating is arranged nearby, facing a cozy firepit. Bright orange doors lead to the interior, surrounded by lush greenery and a privacy fence.

Home in Coxs Creek

The Barrel Proof Bungalow

This stylish 3 bedroom 2 bathroom home on the "Kentucky Bourbon Trail" has been a labor of love and full remodel down to the studs. The Barrel Strength Bungalow is centrally located between Interstate 65 (Jim Beam) and Bardstown's city center. A unique outdoor living space with one of a few hot tubs in Bardstown area Airbnb's. Also offers a firepit, outdoor grill and patio area. More than 15 distilleries within an hour's drive and approximately 30-35m to Downtown Louisville and Churchill Downs.

4.98 out of 5 average rating, 148 reviews

The exterior of the home features a charming white façade with black accents, complemented by a small set of steps leading to the front door. Lush green grass surrounds the property, and a gravel pathway is lined with decorative stones and small shrubs.

Home in Springfield

Bourbon Trail Schoolhouse

Enjoy staying in a piece of history within this old one room schoolhouse converted to a two bedroom home. Sit out on the swing or by the firepit as you enjoy peaceful sounds of the country and the creek adjacent to the property. Located right on the Bourbon Trail with only a 5 min drive to Maker’s Mark, 17 min to Limestone, and 20 min to Log Still Distillery. Venture in to the city of Springfield to learn about Abe Lincoln and his parents, married in the courthouse, still being used to this day!

The image collage features various spaces of a stylish home. A cozy lounge area with a fireplace is shown, alongside an outdoor hot tub surrounded by greenery. The dining area is connected to a deck, and a game room with a bar creates an inviting entertainment space.

4.96 out of 5 average rating, 121 reviews

StillHill: HotTub GameRoom Whiskey Lounge Acreage

Stylish 3 bedroom home located in the Bourbon Capital is a perfect getaway to be still or tour the best Kentucky bourbon from a local whiskey still. Centrally located within 25 miles of 10 distilleries! Close to the Old Kentucky dinner train, the Derby, and a short drive to Louisville & Lexington. Enjoy 5 private acres where you can soak in the hot tub, swing on the patio, sit by the fire and watch the birds and deer. Then relax in our indoor lounge or garage game room after a day of adventures

A cozy living area features dark leather sofas and a rustic wooden coffee table. The room is softly illuminated by decorative lamps and small Christmas trees, while framed artwork and wooden accents adorn the walls, creating a warm and inviting space.

4.96 out of 5 average rating, 241 reviews

Bourbon City Retreat

Escape to a Bourbon City retreat In historic Bardstown Ky named “Most Beautiful Small Town In America”. Experience the Bourbon Trail starting where bourbon was born. Visit Jim Beam American Still House, Heaven Hill Bourbon Heritage Center & Four Roses Warehouse just to name a few. Be sure to visit My Old KY Home and My Old KY Dinner Train. Enjoy southern cuisine at Mammy’s Kitchen, Stephen Foster Restaurant & The Rick house. Enjoy your stay in a quiet, clean & cozy home in Bourbon City Decor.

4.93 out of 5 average rating, 132 reviews

Call Me Old Fashioned! *Heart of Bardstown Square*

Your one-stop shop for where you want to be when visiting Bardstown, Kentucky. A few minutes from amazing restaurants, bars, shops, golf and all the local events for downtown Bardstown. Are you here to see the distilleries? All of the distilleries are just a short drive from this beautiful modern, rustic-styled home. Seeing most or all of them is very doable with this very central location. Finally, we are less than half a mile away from "My Old Kentucky Dinner Train." Hope to see you soon!

4.92 out of 5 average rating, 159 reviews

The cottage features a charming exterior with gray siding and white accents. Two columns frame the welcoming entrance, complemented by a well-maintained lawn and landscaping. Mature trees provide shade, enhancing the outdoor ambiance while the pathway leads to the front door.

Cottage in Bardstown

Historic Bardstown Cottage

Stay with us in Bardstown, named one of "the most beautiful small towns in America." Our cottage is located just three blocks from downtown restaurants, shops, family activities and nightlife. Located on the Bourbon Trail, you are steps from Barton's Distillery and a short drive from several other popular distilleries. Churchill Downs, Keeneland, Mammoth Cave National Park and other popular attractions are within an hours drive making this cottage the perfect base for exploring Kentucky.

A serene outdoor space is illuminated by string lights, creating a warm ambiance at night. Adirondack chairs surround a circular fire pit, with a charcoal grill nearby, set against a backdrop of greenery. The screened-in porch can be seen in the background.

5 out of 5 average rating, 118 reviews

Bluegrass and Bourbon - Peace on the Bourbon Trail

Retreat to your peaceful hangout after a day of exploring all that Bardstown and KY have to offer! Relax by the fireplace and stream a movie on the 75" TV, cook a full meal in the well-stocked kitchen, create a unique cocktail with all the tools you could wish for, breathe fresh air on the screened-in porch that borders greenspace, challenge friends to poker in the game room, grill dinner on our charcoal grill, or roast hot dogs and s'mores on the firepit area. This must be the place.

4.94 out of 5 average rating, 112 reviews

Sunset Porch Sittin'-GameRoom/Bar, 4bedroom

Top off your glass and enjoy a peaceful retreat at the Willett Home. We offer 4 Bedrooms and two full bathrooms, and everything you need to have an enjoyable stay! Relax on the front porch, enjoy the view of the golf course and listen to the bells from My Old Kentucky Home State Park. Located less than one mile to Downtown Bardstown with its many restaurants, festivals and shops. Centrally located on the Bourbon Trail, close to many distilleries!

4.98 out of 5 average rating, 250 reviews

Dome in Mount Washington

My Old Kentucky Dome

An elevated camping “glamping” experience. This brand-new one of a kind geodesic dome is located on a private road that leads you to an overlook featuring one of the most beautiful countryside views in Kentucky. While this getaway experience is nestled deep in the woods, it is also a close drive to all the conveniences you can imagine. This is an off the grid outdoor experience with a ½ mile gravel road including a steep hill. AWD or 4WD advised.