House holiday rentals in Shepherdsville

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!

Bourbon City Retreat

Escape to a Bourbon City retreat In historic Bardstown Ky named “Most Beautiful Small Town In America”. Experience the Bourbon Trail starting where bourbon was born. Visit Jim Beam American Still House, Heaven Hill Bourbon Heritage Center & Four Roses Warehouse just to name a few. Be sure to visit My Old KY Home and My Old KY Dinner Train. Enjoy southern cuisine at Mammy’s Kitchen, Stephen Foster Restaurant & The Rick house. Enjoy your stay in a quiet, clean & cozy home in Bourbon City Decor.

"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!!

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.

The Lakehouse at Progress Park in Derby City

A hidden piece of paradise on 12 acres within city limits of Louisville. The Lakehouse sits on a 2 acre pond, perfect for boating & fishing. Boats & lifejackets are provided. 3BR/1BA, sleeps 8 comfortably in the bedrooms with 2 twin murphy beds in the living room. The back yard has a covered tent & patio has a firepit & gas grill. Progress Park has 11 total units on site. 2 houses, 8 airstreams & a bunk house. *DERBY IS A 3 NIGHT MIN OF THURS-SUN. NO CHECKINS ON FRI OR SAT.

Pickleball*Hot tub*Speakeasy*Bourbon*Pet-Friendly

The Bourbon Skyline is your passport to an unforgettable Kentucky experience. This newly renovated 4-bed, 3 full bath ranch sitting on 8 acres is the epitome of comfort and Kentucky charm. The Bourbon Skyline's hilltop location offers beautiful views over Kentucky landscapes. It's the best of both worlds; countryside, & close to everything! Outdoor dining, fire table & hot tub, corn hole and Pickleball! Just a short drive to Louisville, Lexington, Mammoth Cave & so much more!

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.

"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!

Pinehurst Ranch

Pinehurst Ranch is a remodeled home in a quiet neighborhood. The perfect location to all Southern Indiana and Louisville has to offer, just 7 miles from downtown Louisville and 10 minutes from any dining you could imagine; this location offers the best of both worlds. Conveniently located on a dead end street, this quit neighborhood offers maximum privacy and safety for our guests.