Holiday houses in Bradfordsville

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!

Value · Location · Comfort

StillHill: HotTub GameRoom Whiskey Lounge Acreage

Stylish 3 bedroom home located in the Bourbon Capital is a perfect getaway to be still or tour the best Kentucky bourbon from a local whiskey still. Centrally located within 25 miles of 10 distilleries! Close to the Old Kentucky dinner train, the Derby, and a short drive to Louisville & Lexington. Enjoy 5 private acres where you can soak in the hot tub, swing on the patio, sit by the fire and watch the birds and deer. Then relax in our indoor lounge or garage game room after a day of adventures

Value · Family · Sleep quality

One-Level Family Retreat | Game Room • King bed

Welcome to your Bourbon Trail stay -a cozy, welcoming home perfect for relaxing & enjoying everything Central Kentucky has to offer. This 3-bedroom home sleeps 6 & features a private heated & cooled game room just steps from the house—private bedrooms are perfect for spreading out & unwinding after a day out. Enjoy king & queen beds, cozy living spaces, & a coffee bar to start your mornings right. Perfect for visitors exploring the area, work stays, or spending time with loved ones nearby.

Value · Family · Condition

Bourbon Trail | Walk to Dine | Hot Tub * Fire Pit

Couples love the Kentucky Barrel House located on the Bourbon Trail. Walk Downtown for a steak dinner or shop. Hot tub, Fire pit. 10 Miles from Maker’s Mark, 3.2 Miles from Potter Jane Distilling, Limestone Branch Yellowstone Distillery 8 miles + many more including; Willett, Bardstown Bourbon, Heaven Hill, Jim Beam, James B. Beam, Lux Row. A few miles to Cornerstone Acres wedding venue, Lincoln Legacy Museum + golf. Free Itinerary, huge yard, privacy fence, pet friendly, equipped kitchen.

Value · Location · Hot tub

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.

Location · Family · Access

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.

Location · Family · Getting around

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

Location · Value · Condition

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.

Value · Family · Nearby

Bourbon Belle Farmhouse - 5 Mins From Makers Mark!

Welcome to our family farmhouse, nestled right on the famous Bourbon Trail! This home has been in our family for three generations and offers a warm, authentic Kentucky experience. Relax on the front porch with a glass of bourbon as the sun sets over rolling hills, or wake up to the gentle sounds of farm life. We’re located directly beside the Barrel Head Airbnb. Feel free to reach out if you’re interested in booking both homes to accommodate more guests!

Location · Family · Cleanliness

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

Location · Value · Decor

The Dome At The Ridge-Bourbon Trail Glamping

Escape to the treetops and experience the perfect mix of comfort and adventure in our private geodesic dome. Nestled on the edge of the Kentucky hills, this glamping retreat offers sweeping views of rolling farmland and endless skies. Please note this is a true outdoor experience, and you may encounter wildlife and insects. Perfect for a bourbon trail adventure, a couple’s getaway, or simply unplugging and recharging.

Location · Family · Sleep quality

Coffee with the Squirrels

New chalet only 5 minutes to city of Somerset and 5 minutes to Lake Cumberland! Cozy 1 king size bedroom with custom features throughout. Walk out on your master suite deck and have coffee with nature! Full size bathroom w custom tile. Back deck that overlooks woods and wildlife. Sometimes there is a neighbor who has a dog that barks a couple housss down, I’m sorry if it does, doesn’t happen often

Location · Value · Backyard