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!

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.

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.

Steep Hollow Cabin on Green River - Pet Friendly!

Nestled in the backwoods of Green County, KY. - this little patch of solitude sits on a gently rolling hillside overlooking the Green River. Relax while watching deer and turkey from the back porch, sit around the fire pit at night, cuddle up on the sofa in front of the fireplace or take a walk down to the river. Our 2 BR / 1 B Cabin keeps it simple enough to let you get away from the daily grind of the real world, but affords all the comforts of home. Pet Friendly! Please read below.

Bourbon Trail Country Farmhouse

The Farmhouse is on 5.8 acres and is on the historic Bourbon Trail. The house has a master on the main floor with a queen bed connected to the bathroom. Also, bathroom access from the hallway. There is a large upstairs sleeping space that has one queen bed and two twin beds. Beautiful wrap around porch. There is a separate over the garage apartment across the large driveway that accommodates 2 people as it is a one bedroom with a queen bed. Listed as Bourbon Trail Country Class.

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

Cozy Cabin on the Bourbon Trail

Our place is close to the Bourbon Trail. You’ll love our cabin because of the warm interior and amazing outdoor space. Our place is good for couples, solo adventurers, business travelers, and families. This cabin located in the country on our 100 acre farm, but you are 3 miles from restaurants, groceries, pharmacies and shops. The location is also central to the distilleries: 15mi to Maker's Mark, 35mi to Jim Beam, 50mi to Woodford Reserve, Lexington, and Louisville

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

This is what you call glamping! Get away from it all when you stay under the stars at the Shot Glass Tiny House on wheels located at the end of a backroad surrounded by nature with a small stream out front approximately 3 miles from Maker’s Mark. You will be able to observe wildlife through the big picture window out front and surrounding windows throughout while staying comfortable as you glamp in the rustic style tiny house on wheels .

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.