House holiday rentals in Shepherdsville

4.98 out of 5 average rating, 117 reviews

Home in Springfield

Bourbon Trail 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!

4.99 out of 5 average rating, 201 reviews

"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!!

4.95 out of 5 average rating, 222 reviews

Home in Bardstown

Goldenrod Cottage

The Goldenrod Cottage is a cozy one-bedroom, one-bath retreat located on a quiet corner lot with green space next door and peaceful woods across the street. Inside, you’ll enjoy warm hardwood floors, a stocked coffee bar, and all the comforts of home. You are within walking distance of downtown Bardstown, where you can browse unique shops, enjoy live music, and dine at local restaurants. Nearby, you can tour legendary bourbon distilleries, ride the Dinner Train and explore Bernheim Forest.

4.88 out of 5 average rating, 201 reviews

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.

4.96 out of 5 average rating, 237 reviews

502 House @ Progress Park w/ Game Room

Welcome to Progress Park! A true getaway for fun! Located on a 12 acre Airstream Glamping resort w/ a 2 acre swimming pond. Sleeps 8 comfortably in the beds with 2 leather futons. Enjoy all the luxuries of home w/ added amenities such as a custom game room & luxurious backyard with TV, firepit & grill. Relax, unplug and reconnect in our little slice of heaven. Progress Park has 8 total units on site. 2 houses, 5 airstreams & a bunk house. *DERBY IS A MIN THURS-SUN REQUIRED

4.95 out of 5 average rating, 151 reviews

Lumos Stays: 65" 4K TV, memory foam, kid-friendly

Michael and Ashley (Lumos Stays) welcome you to Louisville, home of bourbon! Centrally located, minutes from the interstate, and close to downtown and the bourbon trail, this is your home base for adventure. Enjoy the 65" 4K Roku TV, fast wifi (~317mbps), green tea memory foam mattresses, modern kitchen, kid-friendly amenities… and did you see that outdoor space? Solo Stove fire pit, hammock, propane grill, and games. Enjoy the private fenced-in backyard and large driveway!

4.99 out of 5 average rating, 163 reviews

Two Bedrooms walking to Expo Center & KY Kingdom!

Spacious private two bedroom in charming Louisville neighborhood. Perfect location is close to everything! Bus Stop and Multiple Restaurants (short walk) Interstate 264 (1 mile) KY Expo Center (1.1) Norton Hospital (1.2) Interstate 65 (1.4) UofL (1.5) Kentucky Kingdom (1.5) Louisville Zoo (2.1) Airport (2.3) Mega Cavern (2.6) Churchhill Downs (2.8) Bardstown Road (3.0) Derby City Gaming (3.4) 4th Street Live (4.3) Waterfront Park (4.5) Yum! Center (4.6) Slugger Museum (5.0)

4.93 out of 5 average rating, 220 reviews

Home in Iroquois

Parkside Pad - Iroquois Park

Central Location! One bedroom & One Bath Home. This newly updated 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.

Superhost

4.89 out of 5 average rating, 215 reviews

*Walk to Churchill Downs!*Close to Expo, UL, YUM!

This house just went under a full renovation! Everything is new and awaits your stay. This property is only .4 miles away from the historic Churchill Downs! A quick Uber or cab ride will get you to 4th Street Live, the Highlands, Frankfort Ave, and many more attractions. We are also only 1.9 miles away from the Kentucky Fair and Expo Center which hosts events every week, concerts, Kentucky Kingdom amusement park, and the state fair.

4.99 out of 5 average rating, 167 reviews

"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!

4.96 out of 5 average rating, 104 reviews

Home in Shepherdsville

WynDown Spot - Long Stays Welcome!

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!