Holiday rentals in Howardstown

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Top-rated holiday rentals in Howardstown

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Top guest favourite

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 favourite

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 favourite

Barn in Campbellsville

4.96 out of 5 average rating, 156 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 favourite

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

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 favourite

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 favourite

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 favourite

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 favourite

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 favourite

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 favourite

Home in Springfield

4.99 out of 5 average rating, 155 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 favourite

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 holiday rentals in Howardstown

Top guest favourite

Farm stay in Hodgenville

5 out of 5 average rating, 13 reviews

Hodgenville -Lincoln’s Lake House w/ Game room

JamesRating, 5 stars2 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 favourite

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 favourite

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 favourite

Cabin in Columbia

5 out of 5 average rating, 30 reviews

Little Cabin in the Woods

KimberlyRating, 5 stars5 days 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 favourite

Home in Elizabethtown

5 out of 5 average rating, 19 reviews

Large Home with Entertainment Options Galore

JohnnaRating, 5 stars2 weeks ago

We stayed for a Ripken tournament and we were right at home! The beds were comfortable, house extremely clean, and such a homey environment. Everything you’d have at home was here! Plenty of name brand supplies! Josh was an excellent host, had great communication and was so welcoming! Highly recommend and will stay here again if we have another tournament in the future.

Superhost

Shipping container in Springfield

4.96 out of 5 average rating, 27 reviews

Box on the Beech

ClarissaRating, 5 stars5 days ago

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

Guest favourite

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 favourite