
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$16,765 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.

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.
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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
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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!
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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
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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.
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Bourbon Trail | Walk to Dine | Hot Tub * Fire Pit
Couples love the Kentucky Barrel House located on the Bourbon Trail. Walk Downtown for a steak dinner or shop. Hot tub, Fire pit. 10 Miles from Maker’s Mark, 3.2 Miles from Potter Jane Distilling, Limestone Branch Yellowstone Distillery 8 miles + many more including; Willett, Bardstown Bourbon, Heaven Hill, Jim Beam, James B. Beam, Lux Row. A few miles to Cornerstone Acres wedding venue, Lincoln Legacy Museum + golf. Free Itinerary, huge yard, privacy fence, pet friendly, equipped kitchen.
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"Call Me Old-Fashioned"in Derby & Bourbon Country!
Welcome to "Call Me Old-Fashioned" - a unique spin on Bourbon w/ a mix of new & vintage amenities! Located in a QUIET & SAFE neighborhood, this family-friendly home is located close to Downtown Louisville & Churchill Downs (18 min), Expo Center & airport (15 min). Bardstown, the Bourbon capitol, is 35 min away. We are also 5 min from Parklands @ Floyds Fork park system - home to 60 miles of hiking, biking & paddling trails & a big playground. Come make yourself at home in our cozy KY home!
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Lilly's Pad
Relax and unwind in between all your Louisville activities. We are close (4.4miles) from SDF airport ,and I65 and the Gene Snyder Freeway are less than 8miles away. There are a plethora of activities from shopping to entertainment venues such as horse racing at historic Churchill Downs, Louisville Zoo, Kentucky Kingdom amusement park, Muhammad Ali museum and childhood home, Louisville Slugger Museum, Valhalla golf club, and 36 Bourbon Distilleries as well as cave exploring and fishing.
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The Angels Share | Walk to Downtown by 1792
At this spacious bourbon lover’s basecamp, you’ll be close enough to breathe in the angel’s share from the rickhouses at Barton 1792 and secluded enough to sleep soundly after a full day of tastings. Enjoy your coffee before heading to downtown Bardstown for the day (just a mile away). Back home, flip through curated bourbon reads, light the fire pit, pour a flight to enjoy, or play games and dine under the stars. A cozy, comfortable home base for enjoying the best of the Bourbon Trail.
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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!
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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!
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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.
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Popular amenities for Shepherdsville house rentals
House rentals with a pool

Little Slice of Heaven-27
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Top 1%• Yard + Porch • 3BR • Peppermint Cottage
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#18 Kentucky Sunrise - Lakefront Home with spacuio
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Downtown Abode Your home away from home.
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Cozy Neighborhood Home - 10 min to Louisville!
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6 Kings + Hot Tub | Near Expo, Track & Downtown
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Bourbon Trail POOL-ZONE! GameRm! Hottub! 3 acres!
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10 min to Lou~Huge Hot Tub~Fenced Backyard~Games
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Weekly house rentals

Beachfront River Cottage
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Colonel Lou Lou's
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Cozy Retreat: Stocked Pond & Firepit near L'ville
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Bluegrass and Bourbon - Peace on the Bourbon Trail
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The North Mantle House
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Cozy cottage, pets, private, convenient, parking
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Barton House - Long Stays Welcome!
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Cozy Little Home
LocationAccuracyNearby
Private house rentals

Whiskey, Horses, & Hospitals
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The Cabin at Mystic Mountain
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Distillery Overlook Barndo Home
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The Retreat on Whitetail Pond
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3 BED/2 BA on Bourbon Trail - Pet Friendly
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The Cottage @ Mellwood
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King Bed | Walk Downtown | Coffee Bar | Cozy Home
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Unique & Historic Gem on Bourbon Trail ~ Location!
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When is the best time to visit Shepherdsville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$25,148 GYD | G$23,052 GYD | G$22,843 GYD | G$29,339 GYD | G$30,178 GYD | G$23,681 GYD | G$27,034 GYD | G$21,795 GYD | G$31,645 GYD | G$22,424 GYD | G$21,166 GYD | G$26,615 GYD |
| Avg. temp | 2°C | 4°C | 9°C | 15°C | 20°C | 25°C | 27°C | 26°C | 22°C | 16°C | 9°C | 4°C |
Destinations to explore
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- Kentucky Exposition Center
- Buffalo Trace Distillery
- Kentucky Kingdom & Hurricane Bay
- Kentucky Derby Museum
- Churchill Downs
- Louisville Slugger Field
- Waterfront Park
- University of Louisville
- Louisville Slugger Museum & Factory
- Kentucky International Convention Center
- Falls of the Ohio State Park
- Jefferson Memorial Forest
- Muhammad Ali Center
- Angel's Envy Distillery
- Castle & Key Distillery
- Big Four Bridge
- James B Beam Distilling
- Bernheim Arboretum and Research Forest
- Frazier History Museum
- Marengo Cave National Landmark
- Bardstown Bourbon Company
- Four Roses Distillery Llc
- Kentucky Science Center
- Cherokee Park





