Vacation rentals in Springfield

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.

Marigold Manor: Eclectic Unit 3 Apartment

Welcome to Unit 3 of Marigold Manor! This apartment features 1 bedroom, 1 bathrooms, a kitchen/living combo, back patio seating, a shared space fire pit, laundry closet, and parking in the rear of the home. While this is a multi unit home, each space has a private entrance and locked interior doors. Whether your stay is short or long, you'll find plenty of amenities to make yourself comfortable. If you want to book the entire home, book each unit. You must climb stairs to access this unit.

BRBN FUN-ZONE! Locally Owned Pope House! 3900sqft!

Centrally located in downtown Springfield, this historic home has been revamped to provide you with all the entertainment that you need! 3900 sq. ft so you can bet that you’ll have plenty of space as a group! Makers Mark sits just 15 minutes away and the bourbon capital of the world, Bardstown, only 20! Want to explore more? Wild Turkey and 4 Roses sit only 30 minutes away and a day trip to Louisville or Lexington is only an hour! Don’t let the party stop after a day out on the bourbon trail!

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.

Cool Deals - Bourbon Trl. + Walk 2 Dine + Hot Tub

Downtown walk to dinner. Hot tub, Fire pit , Bourbon Trail, 10 Miles from Maker’s Mark, many more distilleries. Best boutique style. Complimentary Itinerary, Huge privacy fence pet friendly yard. The Ky Barrel House a unique retreat on the Trail. Equipped kitchen, walk to downtown shops. Minutes to: Maker’s Mark, Willett, Bardstown Bourbon, Heaven Hill, Jim Beam, Lux Row. a couple miles to Cornerstone Acres, The Grove At Silverton Hill, My Old KY Home. Fast WIFI, Fireplace (elec) desk

Lawsons Landing

Lawson’s Landing – A Historic Farm Retreat on the Bourbon Trail Welcome to Lawsons Landing, a peaceful countryside escape in Springfield, KY. Built in the late 1970s by Corbett & Ola Lawson, this home embodies warmth, history, and farm life. Enjoy stunning views, modern comforts, and the charm of a working farm. 3BR | 2BA | Sleeps 6 – Cozy living room, full kitchen, Wi-Fi, outdoor gazebo. Experience the beauty, history, and hospitality of Lawsons Landing-we can’t wait to host you!

Box on the Beech

Escape to our unique cabin nestled along the picturesque banks of the Beechfork River, located in the heart of Central Kentucky, right on the famous Bourbon Trail. Unplug, unwind, and enjoy a drink (we prefer bourbon) while gazing at the stars above and listening to the music of nature. Our tranquil riverside cabin provides the perfect setting for a relaxing and memorable stay. Please note that cell phone service within the unit may be limited, depending on your carrier.

Lincoln Farmhouse-Bourbon Trail-Farm Stay

Tranquility awaits at this newly remodeled farmhouse, offering stunning views of the peaceful countryside. Located just minutes from town, Lincoln Homestead State Park, and Cornerstone Acres, you'll find yourself at the heart of Bourbon Country, with easy access to all your needs and desires. Front and back porches give our guests the perfect spot to sit and relax. Open views all around make you feel like you are truly away from all the hustle and bustle of the world.

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.