Vacation rentals in Chaplin

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Top-rated vacation rentals in Chaplin

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Guest favorite

Cabin in Lawrenceburg

4.98 out of 5 average rating, 121 reviews

Forest Cabin + Bourbon Trail + Hot Tub + Fire Pit

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)

Guest favorite

Train in Lawrenceburg

4.98 out of 5 average rating, 348 reviews

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of elm trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunk-beds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

Guest favorite

Home in Lawrenceburg

4.99 out of 5 average rating, 108 reviews

Cottage On Crooked Creek

A tranquil cottage nestled in the lush countryside and situated right along the Bourbon Trail, this completely renovated rare find is located center of Lawrenceburg, Frankfort and Shelbyville and only 12 min to I-64. With five main bourbon distilleries just 30 min, local wineries within a stone's throw, Churchill Downs and Keeneland Racecourse equidistant and Taylorsville Lake nearby there is little left to be desired when staying here. This is the perfect spot to relax with family and friends.

Guest favorite

Barn in Campbellsville

4.95 out of 5 average rating, 132 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

Chalet in Lawrenceburg

4.96 out of 5 average rating, 178 reviews

Countryside On the Bourbon Trail, 22 Quiet Acres

Welcome to Sea Glass Farm. 1900's restored farmhouse with tons of charm! Full access to 22 acres with beautiful hilltop sunsets. In the heart of The Bourbon Trail, the scenery and wildlife will not disappoint. The location is perfect for a rural getaway or relaxing stop on your Bourbon Trail experience. Minutes from shopping and restaurants; situated between I-64 and The Bluegrass Parkway. This place has been a dream of ours and it will soon be in your dreams as well. Hosted by the owner!

Guest favorite

Farm stay in Springfield

4.98 out of 5 average rating, 633 reviews

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. Breakfast is provided every morning. 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.

Guest favorite

Farm stay in Loretto

4.99 out of 5 average rating, 450 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

Barn in Mount Eden

4.99 out of 5 average rating, 143 reviews

Sweet Hollow Farm

Sweet Hollow Farm is located near Taylorsville Lake. 30 miles from Louisville, 40 miles from Lexington and 25 from Bardstown. We have a small farm with a studio barn apartment. Private entrance with full bath. We also have a beautiful pool that we share with our guests. There is a horseshoe pit, fire pit and multiple outdoor seating areas. Kids and dogs are welcome. We even have space for horses and boats. We can offer peace and quiet, a clear view of the stars and hummingbird theatrics.

Guest favorite

Home in Springfield

4.98 out of 5 average rating, 578 reviews

Cabin Chic on Main

I invite you to take a step back in time while experiencing the comfort and appeal of today in the charming atmosphere of a mid-1800’s original log cabin right in town. It was the home to author Elizabeth Maddox Roberts. There is a large backyard complimented by a grazing hillside and a stream that separates the two. A truly unique setting. And, enjoy a large patio and fire pit to enhance your relaxation at the end of the day. I do not rent for local parties or gatherings.

Guest favorite

Cottage in Hodgenville

4.98 out of 5 average rating, 180 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

Home in Springfield

4.99 out of 5 average rating, 140 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!

Guest favorite

Dome in Mount Washington

4.98 out of 5 average rating, 122 reviews

My Old Kentucky Dome

An elevated camping “glamping” experience. This brand-new one of a kind geodesic dome is located on a private road that leads you to an overlook featuring one of the most beautiful countryside views in Kentucky. While this getaway experience is nestled deep in the woods, it is also a close drive to all the conveniences you can imagine. This is an off the grid outdoor experience with a ½ mile gravel road including a steep hill. AWD or 4WD advised.