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!

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.

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.

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

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

*NEW* Secluded Cabin On Private Lake

Woodland Acres is located in the Heart of Kentucky, with spectacular views all around, year-round! Come enjoy this piece of heaven right on the Bourbon Trail! This unique and spacious hideaway has breathtaking views and is situated just 7 minutes from downtown Lebanon, KY. Enjoy a private lake and fishing dock, take a hike through the vegetation that surrounds you, or enjoy a cup of coffee on the wraparound porch. Ideal for leisure seekers, nature lovers, and families alike!

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

Kentucky Dream on Main

This two-story Victorian abode is a dream getaway, was built in, and is located on the iconic Kentucky Bourbon Trail. With a total of 4 bedrooms, 2 bathrooms, Wi-Fi, and all amenities. This historic home resides right on Main Street in the heart of Springfield Kentucky. This home is perfect for anyone looking to experience historic Kentucky finery with a luxurious, modern design. Guest will be able to check themselves in with a lockbox where they will find a key.

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.

Missy’s unique stays on the bourbon trail .

Welcome to this funky and eccentric property that sits on 72 acres of luscious farmland in the heart of Kentucky, situated along the bourbon trail .. Previously “Missy’s café ) now turned it into a country getaway for family, Friends or sweethearts .. it is set up for intimate events (extra) or just a nice quiet stay .. it has a beautiful view of the farm and surrounding knobs.. not to far away from civilization, but far enough too get away and enjoy nature

Bourbon Trail Bungalow

The Bourbon Trail Bungalow is situated in Marion County, Kentucky, which is renowned for its spot on the Bourbon Trail, Rosewood Golf and Country Club. Lebanon is surrounded by a multitude of attractions, including Green River Lake State Park, which is perfect for adventure enthusiasts. The location also provides an ideal blend of outdoor adventures and cultural experiences. "Just kick back and relax in this calm, stylish space."

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