Traveling in the South? Check out Matador’s accommodations guides:
We hope you love these Louisville bachelor party Airbnbs! Just so you know, Matador may collect a small commission from the links on this page if you decide to book a stay. Listed prices are accurate as of the time of publication.
The Highball Speakeasy Lounge & Retreat
See more photosThis property, officially named “The Highball Speakeasy Lounge & Retreat” has dubbed itself the “hippest, swankiest, most exclusive spot in town.” The building recently underwent an extensive renovation bringing it into modern times — going above and beyond what a traditional Airbnb would offer. The property features two separate, large, unique homes that are both located in a prime spot and connected by a signature “sky deck.” Immediately upon walking in, guests can feel the sense of opulence this property beholds. Admire the vaulted ceilings, exposed brick detailing, the study barnwood floorboards, vintage furniture, and high-end finishing touches like the unique light fixtures and colorful decor. The courtyard is in-between the two separate houses connected by the deck above, and feature colorful adirondack chairs to relax and a vibrant mural on the wall. Spend time in the speakeasy lounge which features big garage doors that open out onto the street. Sing karaoke, or play a game of pool in the billiard room which boasts a beautiful custom design to mimic the look of bourbon on the rocks. It might be hard to actually go out anywhere while staying here, as there’s a myriad of entertainment to choose from, right in the house.
Sixteen-plus guests, six bedrooms
Price: $1,000 per night
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Historic, Luxurious Home Close to Central Park
See more photosThis
large, historic upscale property is just two miles away from all the action of downtown but tucked away from the chaos on a historic court just steps from Central Park. Outside, the beautiful, preserved brick facade pays homage to an era when horse and buggy carriages would pass this house. It’s surrounded by an abundance of well-manicured, lush landscaping providing privacy but not hindering the amount of natural light indoors. Inside, the decor offers a sense of contemporary masculinity with exposed brick walls, clean gray and white interior coloring, and hardwood floors. There’s a game room downstairs featuring a foosball table, a vintage record player, and a porch with rocking chairs to settle in with a drink and relax or wake up with a morning cup of coffee.
Twelve guests, five bedrooms
Price: $517 per night
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Jockey on Gray
See more photosThis property is centrally located in the heart of Louisville, at the intersection of the city’s trendy Nulu, Highlands, and Paristown neighborhoods. Inside, there’s a large entertainment space with foosball, darts, and even a photo booth. The interior is decorated with classic tones of greens and grays mixed with creamy brown leather couches and jockey-themed decor pulling the design together to feel perfectly representative of its name — “Jockey on Gray.” Outside, spend time on the fenced-in outdoor patio which is adorned with picturesque string lights, sit next to the fire pit in one of the sturdy wooden Adirondack chairs, or lounge in the cozy hot tub.
Nine guests, three bedrooms
Price: $322 per night
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Renovated Victorian Home Walkable to Downtown
See more photosThis regal,
recently renovated Victorian home sits in a historic and walkable neighborhood Old in Louisville. Guests will be able to enjoy nearly 5,000 square feet of charming indoor space, which boasts plenty of natural light and is decorated to feel classic — but with a modern Kentucky flare. Immediately upon entering from the beautiful front patio, visitors will step into an impressive foyer with high ceilings, an original fireplace, and a grand staircase leading up to the bedrooms. Downstairs, the dark leather couches and wooden dining room table create an excellent space for gathering. There’s a neon sign reading “It’s all Gold, Baby Baby,” in the “getting ready room” (a room featuring multiple vanities, mirrors, and great lighting) made for memorializing any stay and serving as a perfect photo backdrop to memorialize the weekend. The kitchen overlooks the fenced-in backyard and is fully stocked with cooking essentials. This room’s stained glass detailing adds an extra touch of elegance, complementing the stainless steel appliances.
Twelve guests, six bedrooms
Price: $406 per night
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The Old Time
See more photosThis fully restored
pre-Civil War Row House gives guests a chance to step back in time while enjoying an upscale experience featuring the modern amenities of today. Before it was a rental property, it’s said to have lived multiple lives as a feed mill, a saloon, a grocery store, a restaurant, and an antique store. It’s located two miles outside downtown and in close proximity to multiple nightlife, and entertainment options, breweries, and dining outposts. Inside, the light blue painted walls contrast with the dark leather couches and deep wooden tones creating an atmosphere of masculine luxury. The exposed brick walls and iron fireplaces add a touch of original character, and the kitchen’s stainless steel appliances and granite countertops feel upscale but approachable. Outside, the enclosed patio space features a hot tub and ample seating, connected to the inside where guests can find games like shuffleboard, darts, and foosball.
Ten guests, five bedrooms
Price: $623 per night
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The Saddle Inn
See more photosSitting in the heart of the city just steps from some of the best restaurants and bars in town, The Saddle Inn appears quiet and quaint from the outside — but inside, feels like a
vintage Kentucky mansion adorned with all the best modern decor and amenities. Modern marble countertops complement the white cabinets and caramel-colored wooden floorboards, and bourbon barrels line the fence on the walkway out to the back patio area adding a touch of authentic Louisville character. Spend time out on the double-decker patio (the upstairs deck features a bourbon bar area that overlooks the city), lounge in the hot tub, sit around the fire pit, or get competitive with a game of ping pong or shuffleboard. The kitchen is well-stocked with everything needed to create a tasty meal (even condiments, spices, and coffee). Bedrooms feel cozy, bright, and clean but pay homage to the original building with exposed brick walls and purposefully chosen artwork that tells a story.
Eleven guests, three bedrooms
Price: $1,180 per night
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A Modern House With an Unparalleled Patio
See more photosThis property’s best feature might actually be its backyard, which boasts a brand new, seven-person hot tub as well as a BBQ grill, gas fire pit, patio heater, and full-sized outdoor dining table for gathering under the stars. Inside, there’s a full kitchen and bright, clean rooms that offer lots of natural light and subtle touches of color. It’s a short walk to the best restaurants and bars in the Nulu neighborhood and is a great place to set as a home base for exploring the wider city.
Twelve guests, three bedrooms
Price: $639 per night
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The Bourbon House II
See more photosAt the “
Bourbon House,” which is centrally located in the Historic Germantown district, guests can enjoy the property’s over-the-top, luxurious amenities including a gourmet kitchen, spacious bedrooms, and many separate sitting areas to relax. This house started as a charming 1920s-era bungalow and has since been “opened up” and remodeled to create ample group spaces. Admire the high ceilings, ten-person dining room table, hardwood floors, private “game room” with a foosball table, and large outdoor patio out back encircled by a tall fence for privacy. There’s also a fully equipped kitchen and a grill out back for cooking.
Twelve guests, four bedrooms
Price: $499 per night
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Beautiful Blue Queen Anne Victorian
See more photosThis striking, newly remodeled historic Queen Anne Victorian property is
eye-catching on the inside, and outside. Its beautiful, bright blue exterior makes it one of the most photographed houses in Butchertown, and it’s located within walking distance of multiple shops, bars, restaurants, distilleries, and music venues. Boasting 2,000 square feet of space and preserving many of the property’s original design details, the house welcomes guests to enjoy relaxing in spaces like the upstairs lounge — which features two arcade game consoles — and the large outdoor deck next to a backyard with a fire pit. Bright pops of color in each room add hints of character to the storied walls and there’s plenty of natural light filtering in through the windows.
Ten guests, four bedrooms
Price: $485 per night
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The Oak Barrel Lodge
See more photosThis spacious, restored
lodge-style home is located only five minutes from Downtown Louisville and the local distilleries. The property sleeps up to 18 people on nine queen beds with four full bathrooms and two additional half bathrooms — making it a great spot for large groups. This house is located in Jeffersonville Medical District with close access to the airport and attractions like TopGolf, Louisville Slugger Field & Museum, Louisville Zoo, and more. Immediately upon stepping through the front door, guests will encounter a custom 20-foot floor-to-ceiling bourbon barrel stave accent wall paying homage to the distillery culture in the area. There’s even a “photo ready” neon sign for photo opportunities and a large, custom-built kitchen space for groups to make food together. Leather furniture and dark wood accents give the place a sense of ruggedness. Outside, the connected, fully fenced-in, private backyard area features outdoor games and entertainment like a giant Connect Four board, cornhole, and a gas grill for barbecues on the paved patio.
Sixteen-plus guests, six bedrooms
Price: $532 per night
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Head south to Bardstown to really dive into whiskey country at the Bardstown Motor Lodge
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Less than an hour south of Louisville, Bardstown is the heart of Kentucky bourbon country. Within a stone’s throw, you have Jim Beam, Maker’s Mark, Elijah Wood, and other fine spirits producers offering tastings and tours. The town itself is an engaging place to visit with the guys, with a downtown of historic pubs and restaurants including The Old Talbott Tavern, Scout & Scholar Brewing Co., and Mr. Tubbs. The Bardstown Motor Lodge is
the place to stay here, complete with a pool, bar and lounge, and easy access to the hiking and sightseeing of My Old Kentucky Home State Park, one of the most sought-after outdoors destinations in central Kentuckty — the hotel literally abuts the park itself. The icing? Your room will come complete with whiskey samples.
Price: Rooms from $127
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