
House holiday rentals in Shepherdsville
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Top-rated house rentals in Shepherdsville
Guests agree: these houses are highly rated for location, cleanliness and more.

Barton House - Long Stays Welcome!
Welcome to the Barton House - your home away from home near the Bourbon trail, wineries, and more! The Barton house gets its name from its close proximity to the Barton 1792 distillery & view of Barton rickhouses from the front door. The house sits in a quiet neighborhood & is a 5 min. drive to the dinner train and quaint streets of downtown Bardstown. It is a short 10 min. drive to many of the distilleries and wineries. Celebrating something special or a special occasion? Let us know!

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.

The House with the Orange Door
Located near Churchill Downs, UofL, downtown, the Convention Center and Fairgrounds, and a short distance to restaurants, bars and coffee shops. This single family home offers two bedrooms with queen beds and a pull-out couch in the living room. Enjoy coffee or a relaxing evening cocktail on the back deck. The kitchen is fully equipped and the open living space provides a great area for socializing. Locally made art and decor is on display, adding to the uniqueness of the space.

Private EAST END gem, minutes to everything!
Cozy, East End cottage just minutes from Top Golf, shopping malls, restaurants, entertainment, and other amenities. Easy access to the expressway. Home is well appointed with granite countertops, stainless appliances, hardwood floors, and more. A seasonal creek across from the house can be heard giving the impression of a cabin in the woods with privacy and seclusion, with the convenience of city living at your fingertips. There is also a beautiful park steps away from the house.

The Winning Ticket / Track, Concerts and Life
Are you looking for a fun spot to stay in Louisville 2 miles from the SDF airport, KY Kingdom, Mega Caverns, and Expo Center / Fairgrounds for all the FUN Concerts and Events? PRIME location for Derby goers! 10 minutes from the downtown city? Easy access to all hospitals. Complete with all the comforts of home! Pet-friendly! Look no further. 3 beds / 1 bath Sleeps up to 6 Queen Bed in a closed off bedroom (2) Queen Couch (2) Full size Pull Out couch bed (2) Huge yard

✸ Bright, Modern 3BR | Etown Sports Park 1.8 mi✸
Have fun with the whole family at this modern, stylish place! Minutes to downtown Elizabethtown, less than 2 miles to Elizabethtown Sports Park and Bluegrass Sportsplex, convenient to I-65, and an easy drive to Fort Knox make it a desirable location. Luxury latex foam mattresses and smart TVs in the suite rooms, brand new paint and hardwood look flooring throughout, immaculate cleaning, and smart air purifiers will make you never want to leave! 2 car attached garage.

Quaint Highland's Bungalow
Kick back and relax in this calm, stylish space with equal proximity to beautiful Cherokee Park and all the shops and restaurants on Bardstown Road in the popular Highland's neighborhood. Two bedroom, one and a half bath, completely updated one hundred-year-old home. The backyard offers a beautiful firepit with Adirondack chairs, a patio with dining area and Traeger Grill and plenty of room in the landscaped backyard to throw a ball. Three day minimum stay.

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!

"The Brook" - Louisville
Enjoy a stay at this spacious, beautifully decorated ranch home in East Louisville. Blending organic modern decor and intentional functionality, you will feel relaxed and right at home. The home is nestled in a quiet neighborhood and yet only 1 mile from the interstate - conveniently located, a drive anywhere isn't far. Bring your crew to town to experience a day at the horse track, a bourbon tour, or a Kentucky family getaway!

WynDown Spot
Wind down at this centrally located patio home that comes with an attached garage. This wine-themed home is open and airy, and has a screened-in patio for guests to enjoy. Located 0.2 miles from I-65 and minutes away from grocery stores and restaurants. Forest Edge Winery, James Beam Distillery, and MillaNova Winery are a 10-15 minute drive and many other attractions are nearby. You and your pets can "wine down" at Wyandot!

The Caldwell Highlands/Germantown
Welcome to The Caldwell, a Germantown/Highland area home that includes three bedrooms, one and half bathrooms and sleeps up to five people. The home is within walking distance of several restaurants, bars, retail and vintage stores, and entertainment venues including the Germantown Gables, Logan Street Market and Old Forester’s Paristown Hall. The home features a covered deck, a fenced-in yard as well as home gym.

1 mile to Churchill•Expo Center•Fenced Yard
Book a stay in our lovely 2 Bedroom House for 5 in Louisville, Kentucky and enjoy an unforgettable stay near the top iconic attractions! You'll love our convenient location - just a few blocks from Churchill Downs where the world famous Kentucky Derby takes place! Whether you're traveling with friends or family, our property offers plenty of space and comfort for your group.
Popular amenities for house rentals in Shepherdsville
House rentals with a pool

Pool*Pickleball Bldg*HotTub*Speakeasy*BourbonTrail

Peppermint Cottage Norton Commons w Breakfast

Bourbon Trail Pool&Hottub FUN-ZONE! GameRm! Fish!

Happy Goose Hollow

Farmers Market, Brewery, Bardstown 2 Decks & Porch

4BR Hot Tub. Game Room. Near Lake

Kentucky Sunrise 18- Greet the Sun As it Rises

Pool*Hot tub*Bardstown
Weekly house rentals

Colonel Lou Lou's

The Nicholson Guest House

The Coop

Colonial Hideout | Perfect for distillery touring!

Indian Creek Lodge

Long-term Rental: The Derby Duplex

The Old McDonald Lane

The Barrel Proof Bungalow
Private house rentals

Stylish Louisville Home | Near NuLu & Downtown!

*Bourbon Barrel* Close to Louisville and E-town!

Peaceful Modern Retreat • Prime Location!

Cozy Little Home

Western Gothic Escape • Moody + Modern Vibes

Modern Comfort •Bourbon Trail & Derby•Fenced yard

Minutes to Louville Firepit/fenced yard

The Gold Standard Retreat
When is the best time to visit Shepherdsville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $129 SGD | $139 SGD | $156 SGD | $159 SGD | $208 SGD | $140 SGD | $166 SGD | $134 SGD | $195 SGD | $156 SGD | $156 SGD | $160 SGD |
| 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 |
Quick stats about house rentals in Shepherdsville

Total holiday rentals
Explore 20 holiday rentals in Shepherdsville

Nightly prices starting at
Shepherdsville holiday rentals start at $77 SGD per night before taxes and fees

Verified guest reviews
Over 1,090 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Shepherdsville holiday rentals include wifi 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!
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- Buffalo Trace Distillery
- Kentucky Kingdom & Hurricane Bay
- Kentucky Derby Museum
- Churchill Downs
- Kentucky Exposition Center
- Valhalla Golf Club
- Muhammad Ali Center
- Angel's Envy Distillery
- Falls of the Ohio State Park
- Louisville Slugger Museum & Factory
- Louisville Slugger Field
- Big Four Bridge
- Kentucky Science Center
- Waterfront Park
- Evan Williams Bourbon Experience
- Frazier History Museum
- Cherokee Park
- Kentucky International Convention Center
- L&N Federal Credit Union Stadium
- University of Louisville
- Castle & Key Distillery
- Jefferson Memorial Forest
- Marengo Cave National Landmark
- Four Roses Distillery Llc




