Holiday rentals in Howardstown

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!

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.

Peaceful Getaway in the Country

Enjoy this rustic, yet cozy, two-story barnhouse located near bourbon country. Perfect for a couple's getaway, it has open lofts with a comfy king-sized bed, a kitchen stocked with all the essentials, laundry room, wood burning stove & two bathrooms: one with a walk-in shower & one with a soaker tub. This listing's interior is ready, however the exterior is still a work in progress as we continue to create comfortable outdoor spaces. Must see all pictures to appreciate what this place offers.

Bear-BnB - Relaxing Bear Themed Space

You will be close to everything in Elizabethtown when you stay at this newly remodeled, centrally-located place with a Bear theme. Unique amenities unlike any experience Including: 1Gb Fiber with WiFi, 55" QLED TV, Nest Thermostat with Smoke & Carbon Monoxide, LoveSac Sactional with LoveSac SuperSac coined the ":Bear Chair", Keurig D-Duo Coffee, premium Therapeutic brand mattresses. Full Laundry, and Flywheel Exercise Bikes, Weber Natural Gas Grill and Outdoor Seating area. Included Laundry

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.

Cozy Cabin off Country Road, Close to Bourbon Trl

"Green Acres is the place to be!" Named by a previous owner, who built this cabin as his escape from the city, we would love for it to be your escape too. Off the beaten path, with peaceful scenic views, this cozy cabin features everything you need to disconnect from hectic everyday life, and reconnect with nature or your loved ones. There is a full kitchen with all the necessities, including Keurig, and plenty of sleeping options. There is also a smart tv, electric fireplace, and fire pit.

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.

Magnolia Pines Farmhouse in quiet country setting

This 1,100 SF farmhouse is open and spacious - surrounded by nature with beautiful views. Don't be surprised if you see deer, wild turkeys, rabbits, and fireflies! Very comfortable and relaxing inside and out. There is an inviting deck for enjoying a cup of coffee or a glass of wine by the fire pit. Also, a cozy gas fireplace inside! No smoking allowed. Excellent high-speed internet. Gas and groceries are only 7-15 minutes away. One queen bed and 2 portable twins if needed.

Sunshine and Whiskey

We are located in the heart of the bourbon capital of the world. If your looking for a peaceful quiet country night we are the place for you. We offer a queen size bed and small pull out sofa. There are several local attractions we are 6 miles from Makers Mark, 11 miles to Log Still, 3 miles from the XB Arena (Saturday nights Nov-March), and 13 miles to Historic Bardstown to include Heaven Hill. At night you can relax under our grain bin gazebo. Horse stalls available for $25

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.

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.