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, 103 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

Place to stay in Vine Grove

4.99 out of 5 average rating, 126 reviews

Fort 5400

Rustic 1 bedroom unit on 6 acres. Beautiful creek a couple hundred yards from your door with lovely sunsets. Vaulted living room, dual reclining sofa, 50 inch ROKU TV & dinette. Kitchenette with full size refrigerator, microwave, and Keurig coffee maker. King size bed, cozy electric fireplace, 32 inch ROKU TV and closet with washer/dryer. The grounds are shared with one other tenant. FT Knox-6.2 Miles Elizabethtown Sports Park-15 miles Church Hill Downs-36 miles Boundary Oak Distillary-7 miles

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, 157 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, 471 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, 207 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.

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Other great vacation rentals in Howardstown

Top guest favorite

A spacious dining room features large windows that provide ample natural light and views of the surrounding greenery. A circular table is surrounded by black chairs, while a game table is set nearby. Exposed wooden beams define the room's height and open feel.

Farm stay in Hodgenville

5 out of 5 average rating, 13 reviews

Hodgenville -Lincoln’s Lake House w/ Game room

JamesRating, 5 stars3 weeks ago

I rented Shanna’s place for my family to stay at for my daughter’s graduation. My sister has 2 kids age 10 and 12. They loved the game room. Played the arcade games, air hockey and shuffleboard. My daughters and their cousins loved making s’more’s by the fire pit. The kitchen was wide open making it easy to fix dinner. The bbq was right off the kitchen to grill steaks, skewers and salmon. My dad was able to take his grandkids to the lake and go fishing. At night the living room was large enough for everyone to pile in and watch a movie. I highly recommend this place to anyone with kids, has a big family (house sleeps 12), or just wants a peaceful time in the country to stay at Lincoln’s Lake House.

Top guest favorite

Home in Magnolia

4.96 out of 5 average rating, 110 reviews

Magnolia Pines Farmhouse in quiet country setting

LauraRating, 5 stars2 weeks ago

Sandi was very communicative and friendly. The farmhouse was lovely, peaceful, and private. It had everything we needed and was close enough to everything we wanted to do without being in the middle of a busy town. I would highly recommend this spot for anyone looking for a quiet retreat on their next adventure. Thank you, Charlie and Sandi, for your hospitality and the use of your fabulous property!

Guest favorite

The bathroom features rustic wooden walls and modern amenities, including a round mirror above a vessel sink on a barrel-style stand. A towel basket with folded towels is displayed above a toilet, and a washer/dryer unit is positioned neatly beside a glass shower enclosure.

Cabin in Springfield

4.91 out of 5 average rating, 11 reviews

Manton Getaway!

JacquelineRating, 5 stars1 month ago

The place was cute, clean, and just as described. The host was very responsive and made everything easy. Thank you Joseph!

Top guest favorite

A rustic one-bedroom cabin is surrounded by vibrant autumn foliage, with wooden accents and a welcoming porch. Steps lead to the entrance, while a gravel path guides the way through the tranquil forested area.

Cabin in Columbia

5 out of 5 average rating, 30 reviews

Little Cabin in the Woods

KimberlyRating, 5 stars1 week ago

Can’t recommend this place enough. My husband and I booked the little cabin in the Woods for two nights. We were in town for some local tractor pulls. The cabin had everything we needed for our stay. It was so peaceful after all the noise and mud haha…I was able to disconnect from my phone. I ended up reading a book during my stay which I haven’t done in a while. Would definitely stay here if/when we return to the area.

Top guest favorite

An outdoor seating area features four wicker chairs positioned around a circular stone fire pit, set on a wooden deck. Lush green grass is visible in the background, complemented by a few shrubs and trees, creating a serene outdoor retreat.

Home in Elizabethtown

5 out of 5 average rating, 20 reviews

Large Home with Entertainment Options Galore

ChrisRating, 5 stars2 weeks ago

We absolutely loved our time in this beautiful home! Ilove how clean and spacious it is. The attention to detail and the utilization of the space is brilliant. The owner is kind and very accommodating. This home housed beautiful memories for our family during our stay!

Superhost

A calm river is depicted, bordered by lush greenery and trees that reflect in the water's surface. The tranquil setting offers a serene atmosphere, with riverbanks featuring a mixture of soil and rocks. Gentle ripples can be seen, suggesting a peaceful flow.

Shipping container in Springfield

4.96 out of 5 average rating, 27 reviews

Box on the Beech

ClarissaRating, 5 stars1 week ago

We thoroughly enjoyed this home and it’s beautiful surroundings. The home was clean, quiet, and private. I would definitely return!

Guest favorite

A welcoming porch features a pair of wicker chairs and a small table, positioned in front of a brick facade. Colorful flower pots filled with blooming plants are located on either side, with a decorative metal milk can in the foreground. Natural light filters in through the large window.

Home in Saint Francis

4.91 out of 5 average rating, 11 reviews

'Bourbon Roost' - Charming Home on Bourbon Trail.

BarbaraRating, 5 stars8 months ago

Marilyn’s place was great. Very clean & was well stocked with whatever you need. Location is central to Makers Mark & Log still Distilleries as well as some others in the area. There is a grocery store & Dollar General in Loretto which is a town close by. Bardstown is within 30min also. I would definitely recommend this rental & will use again if I’m back in the area.

Top guest favorite

A gently flowing waterfall is seen cascading over a rocky ledge, surrounded by a natural landscape of trees and foliage. The water pools at the base, reflecting the greenery and rocky texture. Fallen leaves cover the ground, adding a natural touch to the serene environment.

Cabin in Springfield

5 out of 5 average rating, 45 reviews

The Little Cabin on Sunset Ridge

NicoleRating, 5 stars1 month ago

Would stay here again:)

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Vacation rentals in Howardstown

Top-rated vacation rentals in Howardstown

Vacation rentals for every style

Popular amenities for Howardstown vacation rentals

Other great vacation rentals in Howardstown

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