Vacation rentals in Willisburg

4.99 out of 5 average rating, 158 reviews

Cabin in Lawrenceburg

Chic Cabin w/ Trails, Hot Tub & Starry Nights

Privately nestled on over 5 wooded acres & intentionally curated for your stay. Gain access to quiet, immerse yourself in nature, support your rejuvenation, & to tap into your creative flow. 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 distilleries. (Note:18+only)

A circular area features a fire pit surrounded by six blue adirondack chairs. The setting includes grass and greenery in the background, providing a cozy outdoor space for relaxation and gatherings.

4.98 out of 5 average rating, 104 reviews

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!

4.99 out of 5 average rating, 176 reviews

Barn in Lebanon

Walk To Maker’s Mark from Wagon Wheel Barndominium

If you’re looking to relax & kickback in a remote place with family or friends then you have found your space. Our Barndominium is in close proximity to Makers Mark with a 1 minute drive, or approximately 10 minutes walk to visitors center. The whole group will be comfortable in this open spacious and unique rustic place on 8 acres nestled on the banks of Hardins Creek. Many outdoor sitting areas to observe Maker’s crop land and wildlife while enjoying your morning coffee and afternoon drinks.

5 out of 5 average rating, 190 reviews

Farm stay in Lancaster

Serene barn loft in the heart of the Bluegrass

Relax and unwind in this charming barn loft nestled amidst 13 rolling acres on Honey & Vine Farm. This loft is the ideal honeymoon and anniversary space! Enjoy coffee in the morning from Adirondack chairs overlooking the pond, spectacular sunsets from the deck, and absolute serenity in this peaceful setting. Queen bed, private entrance, and beautiful sunsets. The goats and two horses love meeting new friends! 20 minutes to Danville and near hiking, lake Herrington, and Shaker Village.

4.98 out of 5 average rating, 653 reviews

Two horses are seen grazing on lush green grass within a fenced area. A spacious white barn is visible in the background, complemented by a large, well-maintained yard with trees and shrubs lining the property.

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.

5 out of 5 average rating, 213 reviews

The exterior of the stone cabin is framed by lush greenery and flowering plants. Sunlight casts soft shadows across the textured stone walls. A decorative statue stands on a pedestal near the entrance, complementing the natural surroundings.

Cabin in Louisville

Historic Cabin by Bourbon Trail

Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

4.99 out of 5 average rating, 472 reviews

A wall-mounted shelf holds a decorative sign reading 'Home is where your heart is.' Above, a glass bottle and a potted plant offer greenery. Below, a collection of kitchen items includes white flowers, decorative greenery, and checkered oven mitts hanging from hooks.

Farm stay in Loretto

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.

4.93 out of 5 average rating, 222 reviews

An open space features a large glass garage door adorned with a view of greenery, allowing natural light to fill the area. Two metal stools are positioned at a small wooden bar against the wall, providing a cozy spot for relaxation or meals.

Treehouse in Georgetown

Treehouse with TWO outdoor tubs by the creek!

Welcome to your romantic treehouse getaway! Nestled among the trees, this one-bedroom treehouse is the perfect spot if you're looking for a unique & unforgettable experience. The treehouse features a large glass rolling garage door allowing stunning views of the sunset, but the highlight is undoubtedly the double tubs overlooking the creek. ✔ Queen Bed ✔ Outdoor Deck with Seating ✔ Double Outdoor Bathtubs ✔ Outdoor Shower ✔ Composting Toilet ✔ Creek Access ✔ Indoor Cooking Station

4.97 out of 5 average rating, 188 reviews

Aerial view showcases the farmhouse surrounded by lush greenery and pastures. The property includes a large yard shaded by trees, with grazing horses visible nearby. The landscape features a mix of buildings, including a silo and barn, highlighting the rural setting.

Farm stay in Lebanon

Farmhouse in the Country-4 Huge Bedrooms!

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

4.93 out of 5 average rating, 227 reviews

A rustic cabin is situated near a quiet creek, surrounded by lush greenery. The wooden structure features a spacious deck, perfect for outdoor relaxation. The setting offers a serene view of the water and foliage, enhancing the peaceful ambiance.

Cabin in Springfield

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 cozy seating area is showcased on the porch, featuring a gray woven couch and two matching chairs. A coffee table sits at the center, adorned with a lantern. A patterned rug adds texture, complemented by potted flowers near the seating arrangement.

4.99 out of 5 average rating, 157 reviews

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!

5 out of 5 average rating, 123 reviews

A modern shower stall is enclosed by clear glass panels, featuring a built-in niche for toiletries. The shower walls are adorned with white tiles, while the floor showcases patterned hexagonal tiles. A section of exposed brick adds character to the space, complementing the wood flooring.

Loft in Lebanon

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.

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Other great vacation rentals in Willisburg

Guesthouse in Lawrenceburg

Two chickens are positioned in a grassy area, featuring a vibrant rooster in the foreground with a prominent red comb and shiny feathers. A hen with a brown and green plumage is seen in the background, creating a lively farmyard scene.

4.97 out of 5 average rating, 65 reviews

Breezy Ridge Retreat

CaseyRating, 5 starstoday

The stay was absolutely great and they were super helpful and great hosts!

4.9 out of 5 average rating, 88 reviews

A cozy corner of the room features a round table with two woven chairs, set against a neutral wall. A lamp stands nearby, illuminating the space, while an art piece depicting a cow adds character. A plush bed is visible in the background.

Tiny home in Harrodsburg

The Heart of Harrodsburg! Temp workers!

DeniseRating, 5 stars2 weeks ago

Good place to stay and we enjoy our time in the town.

A game of Roll And Score is shown, featuring a smooth, dark lane with vibrant teal accents. The scoreboard glows with colorful lights, indicating the scoring zones. The background reveals a wooden wall and part of a garage door, contributing to the game room ambiance.

5 out of 5 average rating, 15 reviews

Bourbon Trail Treehouse Escape! Cozy/Fun Getaway!

LauraRating, 5 stars2 weeks ago

Cute farmhouse in lovely country setting! GREAT game room! The owner(s) answer any questions immediately and are very available. Family had a blast here!

4.91 out of 5 average rating, 33 reviews

Home in Lawrenceburg

July 4 Bourbon Trail Lakefront Fire Pit Kayak

IanRating, 5 stars1 month ago

This was a lovely country getaway. I had a fantastic time fishing, kayaking, and enjoying the lakefront. If you're looking for a quiet, low-key trip, this is a great choice.

Superhost

The exterior of a two-story Victorian home is presented, featuring white siding and dark shutters. A covered porch with decorative lanterns is flanked by small shrubs and a landscaped lawn. A wheelchair-accessible ramp leads to the entrance, enhancing accessibility.

4.79 out of 5 average rating, 99 reviews

Kentucky Dream on Main

CiaraRating, 5 stars2 weeks ago

Beautiful place located in the heart of Springfield. Used this Airbnb to get ready before my wedding with my girls. Great place for beautiful pictures with the staircase and lots of space for me and the girls.

5 out of 5 average rating, 30 reviews

A country farmhouse is seen from a distance, set against a backdrop of blue skies with fluffy clouds. The well-maintained lawn is bordered by pink flowers. A driveway leads to a garage adjacent to the house, which features a charming white exterior.

Home in Harrodsburg

Charming Pet Friendly Farmhouse in Harrodsburg

AshleyRating, 5 stars3 days ago

They were extremely responsive and helpful. The dogs loved the yard to roam and it was so nice and peaceful

4.98 out of 5 average rating, 48 reviews

A well-lit staircase features dark treads and white railings, leading to an upper level. A chandelier hangs above, illuminating the space. Large windows allow natural light to enter, creating a bright and airy environment. The layout ensures visibility of the stairs and landing.

Home in Perryville

Historical Haven

JessicaRating, 5 stars2 weeks ago

House was perfect for myself, husband and son and great location for what we wanted to do which was tour the perryville civil war battlefield! We really enjoyed our stay. House comfortable, clean with large open living area. Would definitely stay again