House vacation rentals in Shepherdsville

Find and book unique houses on Airbnb

Quick stats about house rentals in Shepherdsville

  • Total vacation rentals

    Explore 20 vacation rentals in Shepherdsville

  • Nightly prices starting at

    Shepherdsville vacation rentals start at G$16,741 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,170 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Wi-Fi availability

    20 of Shepherdsville vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Shepherdsville rentals

  • 4.8 Average rating

    Shepherdsville stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated house rentals in Shepherdsville

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Guest favorite
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
4.9 out of 5 average rating, 125 reviews

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.

Top guest favorite
A spacious living room features a large sectional sofa adorned with light-colored cushions, complemented by a round coffee table. A decorative area rug lies on the floor beneath, enhancing the warmth of the space. Soft lighting is provided by a ceiling fan with lights, and wall mirrors add depth.
Home in Coxs Creek
5.0 out of 5 average rating, 101 reviews

The Bourbon Charm Homestay BourbonTrail Derby PGA

This cozy 3 bedroom house is located only 7 minutes from downtown Bardstown along the Bourbon Trail! Our residence includes three bedrooms (one king size and two queen size beds), a private patio with a grill, a large living room with a huge sectional sofa, and a fully stocked kitchen. We also include a guidebook full of suggestions if you decide you want to go out! We look forward to hosting you while you explore the Bourbon Trail and our unique small town of Bardstown! Smoke-free residence

Top guest favorite
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
4.98 out of 5 average rating, 156 reviews

Bourbon Country 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!

Top guest favorite
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.
Home in Bardstown
4.96 out of 5 average rating, 127 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

Guest favorite
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
4.98 out of 5 average rating, 154 reviews

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.

Top guest favorite
Home in Springfield
4.99 out of 5 average rating, 115 reviews

Last Min Deal | Bourbon Trail | Walk to Dine |

Explore 10+ distilleries from one Bourbon home base in Kentucky! The Kentucky Barrel House is an upscale boutique retreat perfectly positioned between Maker's Mark & Bardstown. Soak in the private hot tub, enjoy the fire pit, or walk downtown for dining. Full kitchen, large fenced yard & pet friendly. NEW Potter Jane 3.2 mi, Limestone Branch/Yellowstone 8 mi, Maker's Mark 10 mi & Bardstown Distilleries including; Lux Row, Heaven Hill, Bardstown Bourbon Co. Custom itinerary included!

Guest favorite
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.
Home in Louisville
4.96 out of 5 average rating, 179 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!

Guest favorite
The exterior of a charming single-story house is shown, featuring a covered porch and stone columns. Lush green bushes frame the entrance, and two seats are visible on the porch. A modest yard surrounds the house, with a clear sky above.
Home in Louisville
4.9 out of 5 average rating, 344 reviews

Quiet Neighborhood Home With Outstanding Location

Situated on a quiet hilltop neighborhood in Clifton Heights, this is the perfect location for a professional or personal visit to Louisville and very animal friendly. It is within 10 minutes of Downtown, Waterfront Park, Nulu, Frankfort Avenue, the Highlands, the Convention Center, and just 15 minutes from historic Churchill Downs. These neighborhoods feature the best dining and entertainment in the city. Just a block away is the Mellwood Arts Center complex with shops and dining.

Top guest favorite
Home in Elizabeth
4.98 out of 5 average rating, 163 reviews

Cabin in the Woods on Lake Close to Louisville Ky

Escape to Little Cedar Lodge, a secluded lakefront cabin just 20 minutes from downtown Louisville. Enjoy beautiful lake views from the huge screened porch, a guest favorite for relaxing among the trees and watching abundant wildlife. This warm, wood-filled A-frame sleeps up to 10 with 2 queen bedrooms plus a spacious loft. Enjoy 2 full baths, a fully stocked kitchen, open living area, fireplace (electric) and plenty of parking. Peaceful, private and close to everything!

Top guest favorite
A spacious living area features a comfortable brown sofa and a wooden coffee table, complemented by a ceiling fan. A dining set occupies one corner, while equestrian-themed artwork adorns the walls. Natural light enters through sliding glass doors, enhancing the overall ambience.
Home in Radcliff
5.0 out of 5 average rating, 102 reviews

Cozy, 3 bedroom home 4 miles from Fort Knox

Discover a cozy home just 4 miles from Fort Knox, offering a personal driveway and high-speed fiber Wi-Fi. With three comfortable bedrooms accommodating up to 6 guests, including a queen, a twin trundle, and two full-size beds. Plus, you're conveniently situated 4.6 miles from the Patton Museum and 4.4 miles from the Chaffee gate/Visitor Center. Experience comfort, convenience, and proximity to local attractions. Your perfect Fort Knox getaway awaits!

Superhost
A comfortable living area is presented with a spacious grey sofa and an armchair positioned on a patterned rug. Natural light streams through the framed windows, and a stone fireplace serves as a focal point, complemented by a wall-mounted television.
Home in Louisville
4.86 out of 5 average rating, 140 reviews

Cute, Cozy, & Clean Home in Louisville

Welcome to this gem that is 20 minutes from Churchill Downs and Downtown Louisville. 15 minutes from the airport and Jim Beam! With parking galore, plenty of bedrooms, and a huge backyard, this is the ideal space for family and friends to reunite and connect. This is the perfect spot to stay to explore Louisville and surrounding areas - close enough to the excitement but far enough away to rest and relax! We would be happy to host you!

Top guest favorite
An open living space features a wall-mounted TV opposite a sectional sofa. A bar-height dining table with seating for four is positioned beside the sofa. Light walls and large windows contribute to a bright atmosphere, while decorative wall art adds visual interest.
Home in Louisville
4.94 out of 5 average rating, 321 reviews

Parkside Pad - Iroquois Park

Central Location! One bedroom & One Bath Home. This home offers a 5 minute walk to wonderful Iroquois Park and the charming Beechmont Neighborhood. Short 5 minute drives to Churchill Downs and the University of Louisville, 10 minute drives to the Airport and Fairgrounds/Exposition Center, and 15 minute drives to trendy NuLu, Highlands, and Germantown neighborhoods. This space will offer the best of what Louisville has to offer.

Popular amenities for Shepherdsville house rentals

When is the best time to visit Shepherdsville?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$25,111 GYDG$23,018 GYDG$22,809 GYDG$29,296 GYDG$30,133 GYDG$23,646 GYDG$26,994 GYDG$21,763 GYDG$31,598 GYDG$22,391 GYDG$21,135 GYDG$26,576 GYD
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