Vacation rentals in Howardstown

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Top-rated vacation rentals in Howardstown

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Top guest favorite

The cabin exterior is nestled within a wooded landscape, showcasing a wooden facade. A welcoming porch is framed by two Adirondack chairs, with stepping stones leading toward the entrance. Twinkling lights hang across the trees, enhancing the tranquil evening ambiance.

Cabin in Lawrenceburg

4.99 out of 5 average rating, 174 reviews

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)

Top guest favorite

A rustic kitchen area features a wooden countertop with bar stools and metallic paneling. Various appliances, including a microwave and stove, are visible. The space is adorned with vintage signs, adding a touch of character to the design.

Barn in Campbellsville

4.96 out of 5 average rating, 169 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

A covered porch features two wooden rocking chairs, facing a serene view of trees with autumn foliage. The wooden railing and floor complement the natural surroundings, creating a peaceful outdoor space for relaxation.

Cabin in Raywick

4.95 out of 5 average rating, 147 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 comfortable living area features a brown leather sofa adorned with plaid cushions, accompanied by a light-colored armchair. A round coffee table rests on a patterned rug, displaying magazines. Indoor plants and a decorative lamp add a touch of greenery and light to the space.

Farm stay in Loretto

4.99 out of 5 average rating, 486 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 cabin is positioned atop a gently rolling hillside, surrounded by trees and open grassy areas. An American flag and a state flag are displayed on a pole near the driveway leading to the entrance. Clear blue skies add to the serene ambiance.

Cabin in Greensburg

4.97 out of 5 average rating, 245 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

A charming farmhouse is visible from across a peaceful pond, surrounded by gently sloping green grass. The house features a wrap-around porch and is framed by trees, creating a serene rural setting. Reflections of the structure and surrounding greenery can be seen on the water's surface.

Home in Raywick

5 out of 5 average rating, 186 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

A vibrant sunset casts shades of orange and pink across the sky, illuminating the spacious property. A gravel driveway leads up to a barn structure, flanked by green grass and a small gazebo. Silhouettes of trees are visible in the background.

Farm stay in Loretto

4.97 out of 5 average rating, 112 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

Guest favorite

A welcoming living area features a dark sofa and an armchair with a light blue cushion. A wooden coffee table sits on a decorative area rug. Natural light enters from the sliding glass doors, highlighting the floral artwork on the wall.

Apartment in Campbellsville

4.99 out of 5 average rating, 163 reviews

Grace Land

Grace Land is a newly renovated apartment. Located just outside the city limits of Campbellsville. We offer a fully equipped kitchen with a Keurig for fresh morning coffee and a variety of coffee flavors provided. King size bed in bedroom and a Lazy Boy sofa bed in the living room. Tv with Cable, Netflix, and Wifi. Covered patio area. 3 miles from Green River Lake and Campbellsville University. 5 miles from Taylor Regional Hospital. Perfect for travel nurses. Keypad entry.

Top guest favorite

A wooden deck leads to the entrance of the cottage, surrounded by lush greenery. A concrete patio features a circular table with benches, providing a shaded outdoor space. The natural setting creates a serene environment, with trees framing the view.

Cottage in Hodgenville

4.98 out of 5 average rating, 220 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.

Guest favorite

The cottage is nestled among lush greenery, showcasing a unique design with corrugated metal and concrete. A wooden deck leads to the entrance, surrounded by neatly arranged flower beds. Windows provide ample natural light while blending harmoniously with the woodland surroundings.

Cottage in Coxs Creek

4.96 out of 5 average rating, 147 reviews

Bourbon Way Cottage

Unique cottage nestled in the woods located along the Bourbon Trail. Centrally located near miles of nature trails in Bernheim Forest & many of the distillery tours. Yet lots of privacy on 10 wooded acers. 8 minutes to Jim Beam Distillery, 8 min to Bernheim Forest, 4 min to Four Roses Bourbon Warehouse & Bottling Tour, 12 min to the City of Bardstown, 30 min to Churchill Downs, 26 min to Louisville International Airport (SDF) NO SMOKING NO PETS

Top guest favorite

The exterior of the tiny house features a warm wood and shingle design. A welcoming red door is flanked by large windows. A wooden deck leads to steps adorned with potted mums, pumpkins, and gourds, while outdoor seating is visible for enjoying the surroundings.

Tiny home in Loretto

4.99 out of 5 average rating, 158 reviews

Shot Glass Tiny House, 3 miles to Maker’s Mark

This is what you call glamping! Get away from it all when you stay under the stars at the Shot Glass Tiny House on wheels located at the end of a backroad surrounded by nature with a small stream out front approximately 3 miles from Maker’s Mark. You will be able to observe wildlife through the big picture window out front and surrounding windows throughout while staying comfortable as you glamp in the rustic style tiny house on wheels .

Top guest favorite

A cozy cabin is framed by lush greenery, featuring a wrap-around porch with decorative lights. Large windows offer an inviting glimpse into the interior, while a wooden exterior blends harmoniously with the natural surroundings. A spacious lawn enhances the serene atmosphere of the property.

Cabin in Hardin County

4.97 out of 5 average rating, 362 reviews

Cabin at Calico Springs

Welcome to The Cabin at Calico Springs, located on 150 acres with nine natural springs, a stream that runs year round, hiking trails, and beautiful forests. This cozy cabin features a great room with living, dining, and kitchen space. There is a private bathroom. The loft has a queen, a bunk bed (2 twins) and a twin. The downstairs has a wrap around porch with room for dining, swinging, and relaxing.