Family-friendly holiday rentals in Shepherdsville

Fort 5400

Rustic 1 bedroom unit on 6 acres. Beautiful creek a couple hundred yards from your door with lovely sunsets. Vaulted living room, dual reclining sofa, 50 inch ROKU TV & dinette. Kitchenette with full size refrigerator, microwave, and Keurig coffee maker. King size bed, cozy electric fireplace, 32 inch ROKU TV and closet with washer/dryer. The grounds are shared with one other tenant. FT Knox-6.2 Miles Elizabethtown Sports Park-15 miles Church Hill Downs-36 miles Boundary Oak Distillary-7 miles

Mini Cow Cottage! Peaceful Farm Getaway

Come enjoy this peaceful private getaway in a beautiful country setting that is still close to town and the bourbon trail. The cottage offers two bedrooms (one king, one queen) and one bath with an open floor plan, fully stocked kitchen, W/D, front and back covered porches, and don't forget the animals! We have mini Highland and High Park cattle, a horse, friendly barn cats, and spacious natural surroundings. There is also a walking trail along the woods, and a beautiful pond. Dogs welcome too!

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

🏆 Featured as one of “5 Unique Stays in Marion County, Kentucky”, January 30, 2026. This is glamping at its best! Stay under the stars at the Shot Glass Tiny House on wheels, tucked at the end of a quiet backroad on the bourbon trail just 3 miles from Maker’s Mark. Enjoy rustic comfort while observing wildlife through the large front picture window and surrounding windows. Explore the Bourbon Trail by day, then return to relax by the fire pit, gazing at the stars in this cozy nature retreat.

Stella Airstream at Progress Park in Derby City

This gorgeous silver bullet is our Stella Airstream, lovingly named after Wally Byam's wife Stella! She is a 1983 Airstream Classic. She's loaded with all the modern amenities! Stella can sleep 6 comfortably with 2 king beds and 2 bunk beds. There's a private toilet/shower with 2 add'l nearby. You'll have a kitchen & covered patio with grill & firepit. There are 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.

Cottage at the Hundred Acre Wood

Escape to the country and take it easy at this unique and tranquil getaway. This beautiful cottage shares the yard and scenery with the owner’s residence, but is a very peaceful & nice space to relax and sleep at the end of your day. You’ll be out in the country but still conveniently located, only about 15 min from everything. 16 minutes from Glendale - Ford Blue Oval plant 14 minutes from Etown Sports Park 16 minutes from downtown Etown & all the great restaurants and stores

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

The City Cottage…quiet, peaceful, and convenient!

A quaint, cozy, and private space close to everything Louisville has to offer. Located on the Northeast side of Louisville, The City Cottage is near the highways for quick access to destinations in and around Louisville. This newly completed space is fresh, clean and created for guests in mind. Are you a couple traveling or a business person wanting more room and comfort than a typical hotel? The City Cottage is for you! (Three night minimum during Derby time.)

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

The Cabin- private,cozy, firepit, hammock, pacman

Take a break and unwind at this peaceful oasis. Blurring the lines between structure and nature, this cabin retreat inspires a feeling of tranquility. The footprint compacts everything one could need- living, kitchen, bed, bathroom, washer/dryer, games and more. Enjoy the peaceful sounds of nature while napping in the hammock. Cook dinner over an open flame in the firepit. Test your skills to beat the high score on PacMan arcade or the foosball table.

Hidden View Cabin

Welcome to Hidden View Cabin, a delightful cabin where seeing wildlife and listening to the sounds of nature are yours to enjoy! Take the scenic drive down the gravel lane to this private and peaceful place located among pine trees and overlooking a one acre pond. Whether you have come to relax and get away from it all or want to visit the many attractions throughout central Kentucky this is the place for you. Only 20 minutes from Lawrenceburg.

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.

Cute, Cozy, & Clean Home in Louisville

Welcome to this gem that is 20 minutes from Churchill Downs and Downtown Louisville. 15 minutes from the airport and Jim Beam! With parking galore, plenty of bedrooms, and a huge backyard, this is the ideal space for family and friends to reunite and connect. This is the perfect spot to stay to explore Louisville and surrounding areas - close enough to the excitement but far enough away to rest and relax! We would be happy to host you!