Vacation rentals in Howardstown

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Top-rated vacation rentals in Howardstown

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Top guest favorite

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.

Home in Springfield

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!

Top guest favorite

Sturdy wooden stairs lead to the upper level of the barnhouse, flanked by rustic handrails. The natural wood grain is showcased throughout, complemented by warm, ambient lighting. A glimpse of the upper loft area is visible through the opening at the top of the stairs.

Barn in Campbellsville

4.96 out of 5 average rating, 159 reviews

Peaceful Getaway in the Country

Enjoy this rustic, yet cozy, two-story barnhouse located near bourbon country. Perfect for a couple's getaway, it has open lofts with a comfy king-sized bed, a kitchen stocked with all the essentials, laundry room, wood burning stove & two bathrooms: one with a walk-in shower & one with a soaker tub. This listing's interior is ready, however the exterior is still a work in progress as we continue to create comfortable outdoor spaces. Must see all pictures to appreciate what this place offers.

Guest favorite

The exterior of the property is shown, featuring a blue siding and a metal roof. A spacious deck is visible, furnished with a dining table and multiple chairs, ideal for outdoor gatherings. The surrounding area is landscaped with bare grass and scattered leaves.

Townhouse in Elizabethtown

4.93 out of 5 average rating, 236 reviews

AIR BnB -- Aviation Themed Comfort

You will be close to everything in Elizabethtown when you stay at this newly remodeled, centrally-located place with Aviation themed highlights. Unique amenities unlike any experience Including: 1Gb Fiber with WiFi, 55" QLED TV, Nest Thermostat with Nest Smoke & Carbon Monoxide, LoveSac Sactional, Keurig D-Duo Coffee, Walker Edison Beds with premium Therapeutic brand mattresses. Full Laundry, and Flywheel Exercise Bikes, Weber Natural Gas Grill and Outdoor Seating area. Included Laundry

Superhost

A wooden picnic table with attached benches is situated on a gravel surface, surrounded by tall trees showcasing autumn-colored foliage. The peaceful setting emphasizes a natural ambiance, inviting relaxation and outdoor dining amid the serene landscape.

Cabin in Raywick

4.94 out of 5 average rating, 143 reviews

Cozy Cabin off Country Road, Close to Bourbon Trl

"Green Acres is the place to be!" Named by a previous owner, who built this cabin as his escape from the city, we would love for it to be your escape too. Off the beaten path, with peaceful scenic views, this cozy cabin features everything you need to disconnect from hectic everyday life, and reconnect with nature or your loved ones. There is a full kitchen with all the necessities, including Keurig, and plenty of sleeping options. There is also a smart tv, electric fireplace, and fire pit.

Top guest favorite

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

4.99 out of 5 average rating, 472 reviews

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.

Guest favorite

A serene river bends gently through lush greenery, bordered by trees and underbrush. The calm water reflects a clear blue sky, creating a peaceful atmosphere. A sandy bank is visible, inviting relaxation and enjoyment of the natural surroundings.

Cabin in Greensburg

4.97 out of 5 average rating, 236 reviews

Steep Hollow Cabin on Green River - Pet Friendly!

Nestled in the backwoods of Green County, KY. - this little patch of solitude sits on a gently rolling hillside overlooking the Green River. Relax while watching deer and turkey from the back porch, sit around the fire pit at night, cuddle up on the sofa in front of the fireplace or take a walk down to the river. Our 2 BR / 1 B Cabin keeps it simple enough to let you get away from the daily grind of the real world, but affords all the comforts of home. Pet Friendly! Please read below.

Top guest favorite

Home in Raywick

5 out of 5 average rating, 181 reviews

Bourbon Trail Country Farmhouse

The Farmhouse is on 5.8 acres and is on the historic Bourbon Trail. The house has a master on the main floor with a queen bed connected to the bathroom. Also, bathroom access from the hallway. There is a large upstairs sleeping space that has one queen bed and two twin beds. Beautiful wrap around porch. There is a separate over the garage apartment across the large driveway that accommodates 2 people as it is a one bedroom with a queen bed. Listed as Bourbon Trail Country Class.

Top guest favorite

An illuminated gazebo stands in a rural setting at night, surrounded by a grassy area. Soft lights enhance the wooden structure, providing a welcoming ambiance. The gravel pathway leads to the gazebo, offering a clear view of the open space nearby.

Farm stay in Loretto

5 out of 5 average rating, 102 reviews

Sunshine and Whiskey

We are located in the heart of the bourbon capital of the world. If your looking for a peaceful quiet country night we are the place for you. We offer a queen size bed and small pull out sofa. There are several local attractions we are 6 miles from Makers Mark, 11 miles to Log Still, 3 miles from the XB Arena (Saturday nights Nov-March), and 13 miles to Historic Bardstown to include Heaven Hill. At night you can relax under our grain bin gazebo. Horse stalls available for $25

Top guest favorite

Cottage in Hodgenville

4.98 out of 5 average rating, 208 reviews

Basil Cottage on the Creek

The Basil (baz-el) cottage is the perfect get-a-way where you can sit on the back porch sipping coffee while overlooking the babbling creek- get back in touch with nature for a much needed break from the stress of every day life. It may be a much needed romantic weekend, a mid- way point as you tour the bourbon trail, visiting Lincoln's childhood home or just a place of your own while in town to visit family, no matter what brings you to our cottage- you will love it here.

Top guest favorite

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.

Home in Springfield

4.99 out of 5 average rating, 156 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!

Top guest favorite

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

5 out of 5 average rating, 123 reviews

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.

Guest favorite

A fire pit surrounded by four chairs creates a cozy gathering space. The seating includes two blue chairs and two gray chairs, arranged on a stone patio. A backdrop of lush greenery enhances the outdoor setting, inviting relaxation and conversation.

Guesthouse in Raywick

4.98 out of 5 average rating, 85 reviews

Peaceful Easy Feelin’

Relax off the beaten path but close to conveniences! We are located within 8 miles to Maker’s Mark and Limestone Branch Distilleries, and 17 miles to Bardstown. We do live in the main house on the farm which is detached and private from this unit. Relax by the firepit in the evening enjoying the peace and serenity. This the perfect getaway for 2 adults! We pride ourselves on making this affordable, beautiful property, the perfect choice for your bourbon adventure.