Holiday rentals in Lebanon

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.

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.

Farmhouse in the Country-4 Huge Bedrooms!

Amenities! You don't need to pay more to get the BEST! My guests are amazed at all the Farmhouse has to offer. The home is on a 3rd generation family farm & has 4 huge bedrooms for your upmost privacy. It is definitely in the country yet only minutes from town. Surrounded by pastures, your only neighbors are the grazing cows. It has 2 wonderful porches, firepit area, renovated garage to hang out in, 320 acres to roam on & 2 fishing ponds. Smoking is allowed outside/2 pet max

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

A Heavenly Home

Serene ~ Peaceful ~ Private ~Modern. Centrally located in the heart of Bourbon Country. This home is an ideal setting to relax and enjoy spending time with friends or family. You will no doubt find this newly constructed home to be cozy, comfortable, and inviting! Enjoy the wonderful outdoor space in a quiet country setting with beautiful scenery and woods, comfortable seating, including a porch swing, a play area for children, and you may even see a deer or two!

Sunny Side Up

Sunny Side Up is situated on the second floor of the Sunny Side Saloon, a historic building with a rich past. Originally serving as a Union Army Commissary during the Civil War, it later transformed into a cherished local establishment known as the Sunny Side Saloon. Here, JH Kearns once sold his own pre-prohibition whisky, often packaged in ceramic jugs. Located in downtown Lebanon, in the heart of Kentucky, Sunny Side stands proudly on the historic Bourbon Trail.

Shepherd's Rest

Whether you’re following the Bourbon Trail, making a pilgrimage to Kentucky’s historic Catholic heartland or simply looking to enjoy the quiet beauty of the Kentucky countryside, Shepherd’s Rest lets you get away from it all keeping you close to your destination. Crafted from repurposed lumber, Shepherd’s Rest has the comforts of modern living with a feel that will take you back two hundred years and a view of the flock that gives Shepherd’s Rest its name.

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 .

Talk Bourbon to Me

Come be our guest on the bourbon trail in Central Kentucky! We have renovated the garage behind our house into a modern and unique studio apartment. If you want to spend your money on bourbon instead of lodging, while still experiencing a high-quality stay, this is your place! We are located 5 minutes from Limestone Distillery, 15 minutes from Makers Mark Distillery, and 30 minutes from Bardstown, Ky.

Downtown Abode Your home away from home.

No cleaning fee ,Beautiful home in downtown Lebanon a prime location for visiting many locations on the Bourbon Trail or the Lincoln Heritage Trail. We are 60 miles from Louisville or Lexington and only 15 miles from Historic Makers Mark Distilery. Several of our guests have stated the downtown abode is the best Airbnb they have ever stayed in. As a added bonus we have no cleaning fee

Spirit on Main

Welcome to Spirit on Main, located in Lebanon, the heart of Kentucky. Located on Main Street, in the middle of all of the local activities, Spirit on Main is prime location for visiting your favorite bourbon spots! Whether you are in town for a couple’s getaway, trip with friends or on business, Spirit on Main will be your home away from home in the beautiful small town of Lebanon.