Holiday rentals in Willisburg

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Top-rated holiday rentals in Willisburg

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Top guest favourite

Earthen home in Willisburg

Restin' Holes Ky Bourbon Trail D *Sauna*HotTub*Gym

Experience the Kentucky village charm at Restin' Holes. Our cozy, unique rental is located on the Bourbon Trail yet still tucked away on 20 acres for relaxation and enjoying many amenities. Be calmed with the peaceful waterfall at our rustic destination. We want you to kick back and make yourselves at home. *Playground*Hot tub*Sauna*Gym*Firepit*Painted Murals Restin' Holes was created with everyone in mind. Book your stay today and discover the perfect vacation & make unforgettable memories.

5.0 out of 5 average rating, 23 reviews

Top guest favourite

Home in Willisburg

Large KY Farm/300yd Golf Range/Bourbon Trl/Animals

Great place for groups! Turnerville Tavern is a unique vintage farmhouse/gift shop/driving range located in the heart of the Bourbon Trl in central KY. With vintage furnishings and a large downstairs living room dedicated to all things Kentucky, groups can gather here and feel at home in the Bluegrass. There are 3 outdoor porches to sit and view the farm and a gift shop. Other amenities include a fire pit, books, ping-pong, wide yard, cornhole, and farm animals. Also you can hike to the creek!

5.0 out of 5 average rating, 39 reviews

Top guest favourite

A charming speakeasy-style room features a well-stocked bar made from rustic barrels, complemented by a vintage chandelier overhead. The walls are adorned with a mural of an antique bar, while a plush rug adds warmth to the space. A staircase leads to the upper level.

Home in Willisburg

1900 House-Bootlegger's Hideout

1900 House is nestled in the rolling hills of KY, located on the Bourbon Trail, six minutes from Bluegrass Pky and Hwy 555. We imagined this was the perfect hideout for Bootleggers. Step back to the Prohibition Era with our Speakeasy Room and elements of the Roaring 20s. Spend the night in the Capone or Remus room, sip your favorite beverage on the front porch rocking chairs or build a roaring fire in the fully fenced in back yard. Explore the history of Prohibition with the comforts of today.

4.95 out of 5 average rating, 19 reviews

Top guest favourite

Home in Springfield

Bourbon + HotTub + FirePit "Fall Magic"

Spend crisp fall days sipping your way through the Kentucky bourbon trail. Walk down the street for dinner/drinks, sink into the hot tub or settle around the fire pit under a cool Kentucky sky. Step inside, sink into velvet. Cozy by the fireplace. An upscale boutique retreat between Maker’s Mark & Bardstown. Distilleries are minutes from the Kentucky Barrel House; Potter Jane 3.2 mi • Limestone/ Yellowstone 8mi • Maker’s Mark 10 mi • Lux Row, Heaven Hill & Bardstown Bourbon Co...

4.99 out of 5 average rating, 121 reviews

Top guest favourite

A collage of images showcases the historic home, featuring well-maintained landscaping, outdoor seating, and a spa. Indoor spaces include a game room, living area with seating, and a kitchen with modern appliances, highlighting various areas suitable for group entertainment.

Home in Springfield

BRBN FUN-ZONE! Locally Owned! Historic! Spacious!

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!

4.99 out of 5 average rating, 141 reviews

Top guest favourite

An outdoor gathering space is highlighted, featuring a circular structure with a metal façade. Strings of lights create a warm ambiance against the dusk sky. A large flat-screen television is mounted on the wall, complementing the open seating area with various tables and chairs.

Guest house in Springfield

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.

4.99 out of 5 average rating, 139 reviews

Top guest favourite

A rustic cabin is nestled among trees, featuring a well-lit entryway and a front deck with two wooden lounge chairs. Soft evening light spills through the windows, creating a welcoming atmosphere. Stone stepping stones lead towards the doorway, enhancing the natural setting.

Cabin in Lawrenceburg

Romantic Cozy Cabin Getaway w/ Firepit & Hot Tub

*NO smoking property (inside or out)* Privately nestled on over 5 wooded acres & intentionally curated for your stay. Gain access to quiet, immerse yourself in nature, and support your rejuvenation. Amenities include on-site hiking trail, artist work space, wood burning stove, covered porch, hammocks, outdoor dining, fire pit, moon garden, salt-water hot tub, & outdoor shower. Close to Beaver Lake & located along the Bourbon Trail, just minutes from Wild Turkey & Four Roses. (Note:18+only)

4.99 out of 5 average rating, 267 reviews

Top guest favourite

An elegant two-story white barn structure is set against a blue sky dotted with clouds. A prominent cupola with a weather vane crowns the roof. Trimmed bushes and small trees flank the sides, adding greenery to the scenic rural landscape.

Farm stay in Springfield

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.

4.98 out of 5 average rating, 694 reviews

Guest favourite

A modern cabin with a dark exterior is located amidst lush greenery, elevated on a wooden foundation. Large glass windows provide open views of the natural surroundings, while a clear path leads to the entrance. Trees surround the structure, enhancing the serene setting.

Shipping container in Springfield

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.

4.93 out of 5 average rating, 58 reviews

Top guest favourite

A view from the covered patio showcases a large open green lawn and a single tree, framed by two columns. The patio features a patterned rug and a black table with a chair, creating a relaxing outdoor space.

Home in Springfield

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.

5.0 out of 5 average rating, 44 reviews

Top guest favourite

An open living area showcases comfortable seating arranged around a neutral rug. Modern kitchen appliances are visible in the background, complemented by dark wood cabinetry. Natural light enters through the window treatments, enhancing the inviting space. A welcoming entrance is seen to the left.

Home in Springfield

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!

4.99 out of 5 average rating, 198 reviews

Guest favourite

An outdoor dining area features a large table surrounded by black chairs, situated on a patio with a decorative rug. Beyond, green fields stretch to the horizon, with a swing set framed by a tree, offering a peaceful view of the surrounding farmland.

Home in Willisburg

Colvin House on Bourbon Trail

Surrounded by farmland, the Colvin House is a spacious, country home centrally located on the Kentucky Bourbon Trail. Whether traveling with family or a large group of friends, our spacious family room, 12 seat dining table, game room, theater area, outdoor dining space or our 5 swing firepit, there is plenty of room to gather together or in separate small groups. The perfect destination for quality time together or a short scenic drive to unlimited adventure.

5.0 out of 5 average rating, 11 reviews