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

Downtown Elizabethtown Mid-Century Charm Home
Cozy 2BR/2BA mid-century modern home, great for tournament families or working travelers. This is also my personal home when I’m not traveling & I share it with guests while I’m away. Sleeping setup: 1 king, 1 full, futon sofa bed and two queen air mattresses. Minutes from Etown Sports Park, downtown, Freeman Lake & the hospital. Fully equipped kitchen plus a Pac-Man arcade game that kids love. Backyard opens to a large community field with baseball and soccer space, plus a grill and fire pit

Bardstown Bourbon Bnb - near My Old KY Home
Welcome to our charming Airbnb in Bardstown, Kentucky, the bourbon capital of the world! Situated in the heart of downtown, our spacious and beautifully decorated home is the perfect retreat for bourbon enthusiasts, history buffs, and nature lovers alike. Boasting of three comfortable bedrooms, each furnished with plush bedding. The living area is bright and airy, with large windows and comfortable seating for you to relax. The fully-equipped kitchen is perfect for cooking up delicious meals.

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.

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.

Cheerful, centrally located 2 bedroom shotgun home
This welcoming home is central to Louisville's most popular and lively neighborhoods, walking distance to many favorite spots. Natural light and unique art fill the home. There is a large deck that overlooks a beautiful cemetery behind the home, and is a perfect place enjoy morning coffee or sunset dinner. A coffee/tea bar is located in the fully equipped kitchen. Charging stations and white noise machines are found in both bedrooms. 2 workstations and a smart TV are also available.

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.

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.

The Highlands Condo/Roof Deck
Our brand new renovated 1 BR condo is located in a famous Highlands’ neighborhood. Conveniently located about 5-8 minutes from Churchill Downs, KFC Yum Center, Cardinal Stadium, Convention Center, Center for the Arts, Downtown Distilleries, Nulu& Germantown area, 12 minutes from the airport. Walking distance to many great restaurants, bars, shops , and parks.

Downtown Louisville 2.5 mi to DERBY
Completely renovated 2 bedroom, 2 baths ( sleeps 6 ) in historic Old Louisville at Central Park (tennis courts and playground). DERBY ready! 2.5 miles to Churchill Downs, Yum Center, Nulu and Waterfront Park (Forecastle). 1 block to St James Court. I mi to UofL. 3.5 mi to Ky Exposition Center. Great walking and biking neighborhood !
Popular amenities for house rentals in Shepherdsville
House rentals with a pool

Pool*Pickleball Bldg*HotTub*Speakeasy*BourbonTrail

5 Baths• King Beds• Hot Tub • Expo & Bourbon Trail

Peppermint Cottage Norton Commons w Breakfast

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

Happy Goose Hollow

4BR Hot Tub. Game Room. Near Lake

Kentucky Sunrise 18- Greet the Sun As it Rises

Pool*Hot tub*Bardstown
Weekly house rentals

2BR Home Near Zoo & Fairgrounds – Family-Friendly!

✸ Bright, Modern 3BR | Etown Sports Park 1.8 mi✸

Sugar Maple Corner: 5min to KY Expo Center and Zoo

Bluegrass and Bourbon - Peace on the Bourbon Trail

Camp Taylor Hideaway Close to Audubon Hospital

Cozy Little Home

Shotgun Rye is ready for Kentucky Derby 2026!

The Barrel Proof Bungalow
Private house rentals

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

Country Retreat on Bourbon Trail - Fire Pit - King

Elizabethtown Sports Park/Bourbon Trail

Last Minute Booking for 1 or 2!

Minutes to Louville Firepit/fenced yard

Modern Comfort •Bourbon Trail & Derby•Fenced yard

The Gold Standard Retreat

3 BED/2 BA on Bourbon Trail - Pet Friendly
When is the best time to visit Shepherdsville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £75 | £80 | £90 | £92 | £120 | £81 | £96 | £78 | £113 | £90 | £90 | £92 |
| 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 £45 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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- Louisville Holiday rentals
- 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
- Louisville Slugger Museum & Factory
- Falls of the Ohio State Park
- Louisville Slugger Field
- Big Four Bridge
- Kentucky Science Center
- Waterfront Park
- Evan Williams Bourbon Experience
- Frazier History Museum
- Cherokee Park
- Kentucky International Convention Center
- Abraham Lincoln Birthplace National Historical Park
- L&N Federal Credit Union Stadium
- University of Louisville
- Marengo Cave National Landmark
- Jefferson Memorial Forest
- Bernheim Arboretum and Research Forest




