Vacation rentals with outdoor seating in Shepherdsville

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of elm trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunk-beds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

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!

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!

Captain's Cabin: Bourbon Trail, History & Romance

Your own log cabin on a wooded hillside with gourmet breakfast served to your door (on weekends)! It's been the location for 5 movies, including Lifetime! Period furnishings and modern conveniences make this an unforgettable retreat. A massive stone fireplace creates a quiet ambiance. Watch wildlife by the lake, creek or from back porch swings. Comfy bed, luxury sheets, high-speed internet, bluetooth stereo and special touches make your stay magical! Ask for Cooking With Bourbon Experience.

"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!!

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.

The Barrel Head

* LOCATED RIGHT ON THE BOURBON TRAIL * At the Barrel Head bed, we strive to make our guest feel as comfortable as possible. This location has been newly remodeled and furnished; a brand new queen size bed, pull out sofa, and coffee bar ensure that you are getting the sleep and energy you need for all of your endeavors while staying on the Bourbon Trail. The Barrel Head is also handicap accessible. There are not any steps, and we have installed a walk in shower for anyone in a wheel chair.

Basil Cottage on the Creek

The Basil (baz-el) cottage is the perfect get-a-way where you can sit on the back porch sipping coffee while overlooking the babbling creek- get back in touch with nature for a much needed break from the stress of every day life. It may be a much needed romantic weekend, a mid- way point as you tour the bourbon trail, visiting Lincoln's childhood home or just a place of your own while in town to visit family, no matter what brings you to our cottage- you will love it here.

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 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

Olive Branch Suite with projector screen in E Lou

This suite is a beautiful private retreat complete with a projector for watching your favorite streaming service for the ultimate movie night. Centrally located and within 10-20 minutes of numerous local hospitals, universities, as well as various restaurants and downtown destinations, our guest suite offers a peaceful retreat in a convenient and safe location. We also provide a fold out desk that guests can use for a remote work space if desired.