Holiday rentals in Shepherdsville

Tiny House Near Louisville

The tiny house is 200 square feet, but has everything you need for a cozy stay! It’s located inside our half acre fenced in backyard which is right off I-65 and is 15 minutes to downtown Louisville. Fast food, restaurants, gas stations, and laundry mat are less than a mile away. The backyard is a shared space with us, so there’s a small chance you see us or our friendly dogs out there. We built the tiny house ourselves, so we take pride in it and hope you choose to experience tiny house living!

Historic Cabin by Bourbon Trail

Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

fenced yard- Bourbon Trail-Derby-driveway parking

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.

Private 1000 sq ft 1-bedroom lower level apartment

Relax in this beautiful wooded setting in Bourbon Country less than 4 miles from I-65. Private entrance into freshly painted 1-bedroom unit with new kitchen and 9' ceilings. Perfectly located near 19 Bourbon Distilleries, 4 Wineries, Bernheim Forest, Knob Creek Gun Range, Churchill Downs and other exciting destinations. Jim Beam Distillery & Forest Edge Winery are 7 min away. There is a seasonal (shared) concrete patio, deck and pool available in the warmer months.

A Little Bit of Kentucky

A unique loft apartment near Louisville, Bardstown and just across the river from Indiana. This is attached to our Wedding venue for the convenience of anyone who is coming in for a wedding. It has its on separate entrance away from the venue so you wont be bothered by anyone. We are more than willing to accommodate you in any way we can. Let us know what you need and we will do our best to meet your needs. Check our guide book for local attractions and mileage

Bourbon Trail 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

Pastel Tiny Home • Romantic Retreat on 15 Acres

💖 Escape to your own pastel paradise—perfect for couples or solo dreamers. This periwinkle 200 sq ft Polly Pocket-inspired tiny home sits on 15 private acres in Louisville. Sip coffee at the bar table, cozy up with AC/heat, and stargaze by the fire pit 🔥 on your private deck with glowing lights ✨ Pet-friendly, peaceful, and totally unique—this is more than a stay. It’s a magical escape made for connection, rest, and unforgettable memories. 🌙🌿

My Old Kentucky Dome

An elevated camping “glamping” experience. This brand-new one of a kind geodesic dome is located on a private road that leads you to an overlook featuring one of the most beautiful countryside views in Kentucky. While this getaway experience is nestled deep in the woods, it is also a close drive to all the conveniences you can imagine. This is an off the grid outdoor experience with a ½ mile gravel road including a steep hill. AWD or 4WD advised.

Cabin at Calico Springs

Welcome to The Cabin at Calico Springs, located on 150 acres with nine natural springs, a stream that runs year round, hiking trails, and beautiful forests. This cozy cabin features a great room with living, dining, and kitchen space. There is a private bathroom. The loft has a queen, a bunk bed (2 twins) and a twin. The downstairs has a wrap around porch with room for dining, swinging, and relaxing.