Holiday rentals in Chaplin

4.99 out of 5 average rating, 154 reviews

Cabin in Lawrenceburg

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)

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!

4.98 out of 5 average rating, 140 reviews

Home in Lawrenceburg

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.

4.99 out of 5 average rating, 471 reviews

Farm stay in Loretto

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.

4.99 out of 5 average rating, 153 reviews

Barn in Mount Eden

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 welcome. We even have space for horses and boats. We can offer peace and quiet, a clear view of the stars and hummingbird theatrics.

4.93 out of 5 average rating, 219 reviews

Treehouse in Georgetown

Treehouse with TWO outdoor tubs by the creek!

Welcome to your romantic treehouse getaway! Nestled among the trees, this one-bedroom treehouse is the perfect spot if you're looking for a unique & unforgettable experience. The treehouse features a large glass rolling garage door allowing stunning views of the sunset, but the highlight is undoubtedly the double tubs overlooking the creek. ✔ Queen Bed ✔ Outdoor Deck with Seating ✔ Double Outdoor Bathtubs ✔ Outdoor Shower ✔ Composting Toilet ✔ Creek Access ✔ Indoor Cooking Station

4.98 out of 5 average rating, 207 reviews

Cottage in Hodgenville

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.

4.93 out of 5 average rating, 227 reviews

Cabin in Springfield

Cozy Cabin on the Bourbon Trail

Our place is close to the Bourbon Trail. You’ll love our cabin because of the warm interior and amazing outdoor space. Our place is good for couples, solo adventurers, business travelers, and families. This cabin located in the country on our 100 acre farm, but you are 3 miles from restaurants, groceries, pharmacies and shops. The location is also central to the distilleries: 15mi to Maker's Mark, 35mi to Jim Beam, 50mi to Woodford Reserve, Lexington, and Louisville

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!

4.94 out of 5 average rating, 139 reviews

Home in Harrodsburg

The Betsy Sweat Cottage.

****This home is all Electric . Carbon Monoxide detector located beside bed .This is a TINY Home..The plant collection will provide you with natural oxygen and new split heating and cooling will clean the air providing you with a restful sleep (day or nite) Close to Danville 9.5 miles (15 minutes away). , Frankfort 32 miles (40 minutes away) Lexington ****FYI- There is an additional charge of $30 extra charge for more than 2 guest.. children no extra charge.

4.99 out of 5 average rating, 567 reviews

Cabin in Lawrenceburg

Bourbon Trail Cabin on the Farm

Recognized by AirBnB as the “2021 Top New AirBnB in the State of KY”!Overlooking rolling hay fields, and surrounded by wooded farm land, this cabin features barn wood walls, hardwood floors, handcrafted bourbon barrel sink, king bed, leather sleeper sofa, and custom built kitchenette. Located on a working cattle farm, see cows, goats, a donkey and horse, & our pet free-range pig! In the heart of the Bourbon Trail in the home of Wild Turkey and Four Roses.

4.98 out of 5 average rating, 166 reviews

Dome in Mount Washington

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.

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4.97 out of 5 average rating, 90 reviews

Home in Bardstown

StillHill: HotTub GameRoom Whiskey Lounge Acreage

JessicaRating, 5 stars1 week ago

Just as pictured, beautiful and perfect for our stay. It rained during our stay, but we picked the right place with the game room, hot tub, plenty of hang out areas, ect. They provide plenty of pleasant amenities: shampoo/condition, body wash, towels, keurig. Near by activities, restaurants- delivery options available, ect. And checkout rules make it a breeze! Thanks for sharing your home with us.

4.91 out of 5 average rating, 23 reviews

Home in Taylorsville

Bourbon Trail Lake Home w/ Hot tub & King Bed

SteveRating, 5 stars2 days ago

The place was everything we wanted ton our stay. Sarah was fantastic in responding to any of our questions. I would definitely stay here again!

5 out of 5 average rating, 29 reviews

Home in Shelbyville

The Back 40

DanRating, 5 stars2 weeks ago

We had an absolutely amazing stay at this beautiful Airbnb during our bourbon hunting trip in Kentucky. The location couldn’t have been more perfect—less than 30 minutes from both Buffalo Trace and downtown Louisville, which made our bourbon adventures super convenient. The property itself was spotless and incredibly comfortable. One of the highlights was the huge covered deck, which became our sanctuary during a rainy day. We spent hours out there just relaxing, listening to the peaceful sounds of the tranquil creek that flows right in front of the deck. It was like something out of a postcard. Nature lovers will feel right at home here. We saw plenty of deer, hawks soaring above, and even a small herd of cattle that strolled by at nearly the same time each evening—like clockwork! It added such a unique charm to the whole experience. We also made full use of the kitchen and grill, cooking up some delicious local beef while sipping on bourbon in the serene countryside setting. It wa

4.95 out of 5 average rating, 57 reviews

Home in Lawrenceburg

Bourbon Crossing II

MatthewRating, 5 stars1 day ago

Great place to stay if you’re in the area, I would stay again.

Superhost

Home in Versailles

5 out of 5 average rating, 3 reviews

Luxe Bourbon Trl~Game Rm~Golf Sim~Hot Tub~Fire Pit

WilliamRating, 5 stars4 days ago

Absolutely wonderful stay, easy to town, property is exquisitely done. Awesome touches!! Loved the hot tub! Game room is phenomenal. Property had wildlife daily to photograph with deer, squirrels, and birds.

5 out of 5 average rating, 39 reviews

Walk to dinner. Bourbon. Hottub. Trail

DeborahRating, 5 stars3 days ago

This charming home has lots of character and met our needs very well. I even thought it was better inside than the pictures showed. The beds were very comfortable and clean. We enjoyed roasting marshmallows outside in the fire pit while enjoying the hot tub. This home was easy to access and in a very quiet neighborhood. Thank you Samantha for being so accommodating. We will definitely stay here again.

4.87 out of 5 average rating, 60 reviews

Home in Taylorsville

Little Slice of Heaven-27

AmyRating, 5 stars2 weeks ago

We stayed 3 nights for my Sisters wedding at the club house area by the pool. Its walkable there. The cabin was spacious, very clean and had everything you needed and some. Even the master bed was very comfortable to me. It was nice having 2 full bathrooms as well. My Son enjoyed the hot tub, I missed out due to decorating. I even wanted to stay an additional night or even two, it was so nice, but it was already rented out, that speaks to what Im saying. I most definitely will be back and will only request Cabin #27! The area is a great escape from the city and the everyday hustle called life. I see myself returning several weekends for a short get aways to just breathe and relax. Thanks for sharing your place. It was everything we wanted.