
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.

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.

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

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!

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

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.

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!

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!

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.

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!

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!

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!

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
House rentals with a pool

Little Slice of Heaven-27

Pool*Pickleball Bldg*HotTub*Speakeasy*BourbonTrail

#18 Kentucky Sunrise - Lakefront Home with spacuio

Cozy Neighborhood Home - 10 min to Louisville!

Bourbon Trail POOL-ZONE! Bourbon Fest! Keeneland!

Top 1%• Yard + Porch • 3BR • Peppermint Cottage

10 min to Lou~Huge Hot Tub~Fenced Backyard~Games

Downtown Abode Your home away from home.
Weekly house rentals

The Angels Share | Walk to Downtown by 1792

"Call Me Old-Fashioned"in Derby & Bourbon Country!

Aviation Elation

502 House @ Progress Park w/ Game Room

Barton House - Long Stays Welcome!

Colonel Lou Lou's

Cozy cottage, pets, private, convenient, parking

Cozy Little Home
Private house rentals

Whiskey, Horses, & Hospitals

Cozy Home Near the Bourbon Trail & KY Derby

Bourbon Trail Retreat | 21 Acres Near Louisville

The Hearthside Haven: A Relaxing Rural Getaway

Sunset Strip

Elizabethtown Sports Park/Bourbon Trail

King Bed | Walk Downtown | Coffee Bar | Cozy Home

The Cabin at Mystic Mountain
When is the best time to visit Shepherdsville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$25,111 GYD | G$23,018 GYD | G$22,809 GYD | G$29,296 GYD | G$30,133 GYD | G$23,646 GYD | G$26,994 GYD | G$21,763 GYD | G$31,598 GYD | G$22,391 GYD | G$21,135 GYD | G$26,576 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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- Knoxville Vacation rentals
- Kentucky Exposition Center
- Buffalo Trace Distillery
- Kentucky Kingdom & Hurricane Bay
- Kentucky Derby Museum
- Churchill Downs
- Louisville Slugger Field
- Waterfront Park
- Kentucky International Convention Center
- University of Louisville
- Louisville Slugger Museum & Factory
- Jefferson Memorial Forest
- Muhammad Ali Center
- Falls of the Ohio State Park
- Castle & Key Distillery
- James B Beam Distilling
- Angel's Envy Distillery
- Marengo Cave National Landmark
- Bernheim Arboretum and Research Forest
- Bardstown Bourbon Company
- Frazier History Museum
- Big Four Bridge
- Four Roses Distillery Llc
- Cherokee Park
- Kentucky Science Center





