Family-friendly holiday rentals in Shepherdsville

Hot Tub + Bourbon Trail | Free Custom Itinerary

Hot tub, Fire pit , Bourbon Trail Location, 10 Miles from Maker’s Mark and many more distilleries. Boutique style. Customized Complimentary Itinerary , Walkable restaurants, Fenced dog yard. The Kentucky Barrel House a unique retreat on the Bourbon Trail. Equipped kitchen, walk to downtown restaurants. Minutes to: Maker’s Mark, Willett, Bardstown Bourbon, Heaven Hill, Beam and many more. Near Cornerstone Acres Events, The Grove At Silverton Hill, My Old KY Home. Fast WIFI, Fireplace (electric)

The Barrel Proof Bungalow

This stylish 3 bedroom 2 bathroom home on the "Kentucky Bourbon Trail" has been a labor of love and full remodel down to the studs. The Barrel Strength Bungalow is centrally located between Interstate 65 (Jim Beam) and Bardstown's city center. A unique outdoor living space with one of a few hot tubs in Bardstown area Airbnb's. Also offers a firepit, outdoor grill and patio area. More than 15 distilleries within an hour's drive and approximately 30-35m to Downtown Louisville and Churchill Downs.

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

The Getaway in Bourbon Country with Breakfast

Located in the heart of the Bourbon Trail. Come and enjoy the peace and quiet of country living, but still close enough to cities. When you first arrive, you will find the entrance on a large, covered patio. There is a gas grill there for your use. We also have a fire pit, so bring wood. Feel free to take a walk down to the river at the bottom of our property. There you will find a park like setting where you can relax and listen to nature if you like. Eggs, bacon and biscuits provided.

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.

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 cattle, a horse, 3 very friendly barn cats, and spacious natural surroundings. There is also a walking trail along the woods, and a beautiful pond. Dogs welcome too!

Bluegrass and Bourbon - Peace on the Bourbon Trail

Retreat to your peaceful hangout after a day of exploring all that Bardstown and KY have to offer! Relax by the fireplace and stream a movie on the 75" TV, cook a full meal in the well-stocked kitchen, create a unique cocktail with all the tools you could wish for, breathe fresh air on the screened-in porch that borders greenspace, challenge friends to poker in the game room, grill dinner on our charcoal grill, or roast hot dogs and s'mores on the firepit area. This must be the place.

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

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.

Parkside 3 Bedroom apartment

This apartment is in a growing and diverse part of Louisville. It is located in the Shelby Park neighborhood just a few blocks from Old Louisville and a few blocks from Germantown. The house has been recently renovated and it is beautiful. Virtually everything in the apartment is new. The bathroom feels like a spa with a freestanding modern tub and a walk in shower with double shower heads and a tankless hot water heater for unlimited hot water.

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.

WynDown Spot

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!