Holiday rentals with outdoor seating in Shepherdsville

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.

Bourbon Cabin - Speakeasy/HotTub/Arcade/Derby

🏡 Bourbon Trail Hideaway – A spacious 5BR, 3.5BA log cabin on 6 private acres, just 9 mins from Jim Beam! 🍂 Blending rustic charm with modern comforts, this retreat features a Brand NEW speakeasy lounge, hot tub, fire pit, wraparound decks, arcade games, and a well-stocked kitchen. Enjoy breathtaking sunsets, fast WiFi, plush seating, Smart TVs, and a cozy ambiance, plus luxurious beds, spa-like bath, and plenty of space to relax or entertain. Perfect for groups, couples & bourbon lovers! 🥃✨

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

Walking Bridge, Putt Putt House

NEW LISTING: Welcome to our walking bridge home on Pearl St. We have a hot tub, putt putt, and all the fun you can think of in one home. Steps away from restaurants, shopping, and bars, as well as the walking bridge to Louisville. This home is closer to the fun in Louisville than most neighborhoods in Louisville itself. Go out or stay in, you're guaranteed to have a great time in this newly renovated gem. We have high quality mattresses, and smart TV's in both bedrooms and the living room.

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.

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.

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

★Jenny's Place - Basement Suite, Private Entrance★

Welcome to Kentucky & Bourbon Country! Jenny's Place includes your own private lower-level walkout suite, with all the amenities, nestled in a quiet subdivision. We are centrally located near many events and activities, including the Bourbon Trail, Four Roses Bottling (5 min away), Jim Beam Distillery (10 min away) and Bernheim Forest (10 min away). We are conveniently located 15 minutes from Bardstown, the Most Beautiful Small Town in America. Come see us!

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

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!