Holiday rentals in Shepherdsville

Peaceful Getaway in the Country

Enjoy this rustic, yet cozy, two-story barnhouse located near bourbon country. Perfect for a couple's getaway, it has open lofts with a comfy king-sized bed, a kitchen stocked with all the essentials, laundry room, wood burning stove & two bathrooms: one with a walk-in shower & one with a soaker tub. This listing's interior is ready, however the exterior is still a work in progress as we continue to create comfortable outdoor spaces. Must see all pictures to appreciate what this place offers.

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

Welcome to the Bourbon Barrel house! We are located in the city of Shepherdsville, KY. We are just 15 minutes south of Louisville, KY, 20 minutes north of Elizabethtown, KY and 30 minutes from the Blue Oval Plant in Glendale. This home would be a perfect base for the Bourbon Trail as well since we are only 10 minutes away from the Jim Beam distillery. Shepherdsville is a smaller town but we have a Super Walmart, Kroger, a ton of fast food options, and a 1.5 mile go cart track at Kart Country.

"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!!

Modern Comfort •Bourbon Trail & Derby•Fenced yard

Welcome to your perfect Kentucky retreat! Nestled in a peaceful neighborhood, this spacious home offers everything you need for a comfortable stay. Enjoy a fully fenced backyard—ideal for pets and kids—a large back deck with a grill, and a roomy garage and driveway for convenience. Inside, relax on a super-comfy couch in the living room, cook up a feast in the full kitchen, and take advantage of two full bathrooms and a washer/dryer. It’s perfect for families, groups, and pet owners.

Cozy Studio in Brooks

Step in to a bright and cozy studio apartment with Moroccan flair - only 20minutes from downtown Louisville, Kentucky Kingdom and Churchill Downs, 15 minutes from the SDF airport and Bernheim Forest and 10 minutes from miles of Jefferson Memorial forest trails. Located on a country hillside with a separate entrance and a high outside deck that opens to the treetops, it's the perfect place to relax but still be close to all that Louisville has to offer.

Bourbon Way Cottage

Unique cottage nestled in the woods located along the Bourbon Trail. Centrally located near miles of nature trails in Bernheim Forest & many of the distillery tours. Yet lots of privacy on 10 wooded acers. 8 minutes to Jim Beam Distillery, 8 min to Bernheim Forest, 4 min to Four Roses Bourbon Warehouse & Bottling Tour, 12 min to the City of Bardstown, 30 min to Churchill Downs, 26 min to Louisville International Airport (SDF) NO SMOKING NO PETS

Shot Glass Tiny House, 3 miles to Maker’s Mark

This is what you call glamping! Get away from it all when you stay under the stars at the Shot Glass Tiny House on wheels located at the end of a backroad surrounded by nature with a small stream out front approximately 3 miles from Maker’s Mark. You will be able to observe wildlife through the big picture window out front and surrounding windows throughout while staying comfortable as you glamp in the rustic style tiny house on wheels .

WynDown off the Bourbon Trail

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!

“Crossroads” connecting Louisville and Bardstown

This apartment is good for couples, solo adventurer and business travelers. It is 10 miles south of Louisville, 18 miles north of Bardstown, 18 miles west of Taylorsville Lake and 1 hr away from Lexington. It is close to a very cool park, The Parklands, where you can hike, bike and kayak. The apartment is centrally located in the “crossroads” of several really cool communities in horse country, Kentucky.