Family-friendly holiday rentals in Lebanon

Bourbon Trail POOL-ZONE! Bourbon Fest! Keeneland!

This two-story country-side home is sure to keep you entertained while also having a relaxing vibe for your getaway. Nestled just off the Bourbon Trail, Makers Mark and historic Bardstown are just a short drive. Proximity to Louisville and Lexington is great too! Sitting on 3 acres, this home Features 4 bedrooms, 2 and a half bathrooms! Amenities include a newly constructed fenced in Inground Pool(open Mid March- end October),WiFi/DirecTV, Pool Table, Ping Pong Table, and GoldenTeeArcadeMachine!

Family · Kitchen · Hot tub

Bourbon Country 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!

Kitchen · Indoor spaces · Condition

Lofty Lodge on the Bourbon Trail

Come to the Bourbon Trail in the Heart of Kentucky! Stay at our beautiful lodge with large common areas perfect for hanging out! Our space is great for family trips, work retreats, or a couples get away! The lodge is located just 3 miles from from restaurants, groceries, pharmacies and shops. But at the Lodge you will enjoy the peace of the country. We are central to all the bourbon distilleries: 15mi to Maker's mark, 35mi to Jim Beam, 50mi to Woodford Reserve, Lexington and Louisville.

Kitchen · Family · Layout

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.

Indoor spaces · Family · Parking

Last Min Deal | Bourbon Trail | Walk to Dine |

Explore 10+ distilleries from one Bourbon home base in Kentucky! The Kentucky Barrel House is an upscale boutique retreat perfectly positioned between Maker's Mark & Bardstown. Soak in the private hot tub, enjoy the fire pit, or walk downtown for dining. Full kitchen, large fenced yard & pet friendly. NEW Potter Jane 3.2 mi, Limestone Branch/Yellowstone 8 mi, Maker's Mark 10 mi & Bardstown Distilleries including; Lux Row, Heaven Hill, Bardstown Bourbon Co. Custom itinerary included!

Kitchen · Family · Parking

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.

Kitchen · Indoor spaces · Hospitality

Hilltop Haven

Enjoy the sounds of nature, and amazing views with your morning coffee on the deck. Deck overlooks a vast rural setting that is part of the Green River Valley. Second story one room cabin with open vaulted ceilings ( must be able to climb stairs to access). Sleeping for 4 and possible 5th with couch. Full kitchen with bar, ¾ bathroom. Large deck for enjoying the countryside views and show stopping sunsets. Pets welcome with fee. Close to town and amenities. I mile from river access.

Kitchen · Family · Quiet

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

Kitchen · Family · Comfort

Walk To Maker’s Mark | Wagon Wheel Barndominium

🏆 Voted one of the Top “5 Unique Stays in Marion County, Kentucky” – January 30, 2026. Welcome to the Wagon Wheel Barndominium, just a short walk to Maker’s Mark on the Bourbon Trail. If you’re looking to relax and kick back at a remote place on the Bourbon Trail with friends you’ve found your space! This unique rustic Barndominium on 8 acres along Hardins Creek sleeps 6 comfortably. Relax with multiple outdoor seating areas to enjoy creek views, Makers cropland, and wildlife.

Indoor spaces · Family · Walkability

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.

Kitchen · Family · Hospitality

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

Kitchen · Indoor spaces · Decor

Downtown Abode Your home away from home.

Our prices now include Air B&B service fee. 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

Kitchen · Indoor spaces · Condition