Holiday rentals in Chaplin

Romantic Cozy Cabin Getaway w/ Firepit & Hot Tub

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)

Value · Family · Parks

StillHill: HotTub GameRoom Whiskey Lounge Acreage

Stylish 3 bedroom home located in the Bourbon Capital is a perfect getaway to be still or tour the best Kentucky bourbon from a local whiskey still. Centrally located within 25 miles of 10 distilleries! Close to the Old Kentucky dinner train, the Derby, and a short drive to Louisville & Lexington. Enjoy 5 private acres where you can soak in the hot tub, swing on the patio, sit by the fire and watch the birds and deer. Then relax in our indoor lounge or garage game room after a day of adventures

Value · Family · Accuracy

Bourbon Trail Estate | Hot Tub | Al Fresco Living

Nestled in the heart of the Bourbon Trail, The Commonwealth is a spacious home that feels luxurious, yet still welcoming. When you enter the front doors, you will be greeted by a grand double staircase and plentiful gathering space. Each of the five bedrooms has its own dedicated full bathroom, making this perfect for a large group or couples' getaway. Situated near Louisville and Bardstown, you have quick access to over 20 distilleries, as well as quaint downtown areas and Taylorsville Lake.

Location · Family · Getting around

Relaxing Bourbon Trail Countryside Home & GameRoom

Welcome to Bourbon Country. This spacious 3 bed 3 bath open floor concept home sits on 5 acres of country hillside with beautiful Kentucky sunsets. It is centrally located near all of the local distilleries: Heaven Hill 20mi, Maker’s Mark 32mi, Jim Beam 31mi, and Buffalo Trace 37mi. After a busy day exploring, come home and relax or have some fun in the game room. This house is the perfect place to stay for a weekend getaway or a longer vacation. Discounts may be available! Msg for details.

Location · Family · TV

Charred Oak Reserve-Sleeps 10 Hot Tub, Firepit

Welcome to this new, central base camp on the Bourbon Trail. This modern black barn getaway sits on 5 acres, perfectly located between Anderson & Nelson counties, offering unbeatable access to ALL of Kentucky's best bourbon distilleries . The home's interior is comfortably designed to keep you fully immersed in the spirit of Kentucky after a long day of tastings and touring. There is plenty of space for guests to relax, rest, or gather for play. *Must be at least 25 years of age to book.

Location · Family · Amenities

Distillery Overlook Barndo Home

Welcome to Distillery Overlook! This private barndominium style home is nestled on 7 acres in the Kentucky countryside, overlooking one of Heaven Hill Distillery’s barrel reserves. This home sleeps up to six, with ample space to relax and enjoy the views. Located only 10 minutes from downtown Bardstown, the Bourbon Capital of the World, this luxurious space is designed for entertaining, comfort, and convenience to local attractions, including the best the bourbon trail has to offer.

Family · Location · Comfort

Cottage Retreat at Tiwazzen Farm

The Tiwazzen Farm cottage lies in the peaceful hills of Central Kentucky. It is ideal for a weekend recharge, disconnect or a place to find your center and connect with nature. If you want peace, quiet and tranquility, look no further! If it's Bourbon, Horses and Urban night life you're into, Tiwazzen Farm is perfectly located between Bardstown, Louisville and Lexington. If you're looking for a day at the lake, we are minutes from both Willisburg and Taylorsville Lake State Park.

Location · Family · Quiet

Ridgemont Reserve|Sleeps 18|Hot Tub|Sauna|Arcade

Welcome to the Ridgemont Reserve in the heart of Kentucky’s iconic Bourbon Trail. Located in a peaceful country setting on 14 acres, this serene retreat can comfortably accommodate up to 18 guests with 7 bedrooms and 5.5 baths. Designed with comfort, style, and entertainment in mind, our thoughtfully curated home is the perfect destination for families, friends, or corporate groups looking to unwind, explore, and indulge in the best the Bluegrass State has to offer. Pets allowed!

Value · Family · Checkout

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.

Location · Family · Parking

Bourbon Country Cabin

Nestled in the Heart of Bourbon Country sitting on 80 acres of Kentucky woodlands this charming loft style cabin makes a great central location to visit all the local distilleries on the Kentucky Bourbon Trail! Enjoy exploring the walking trails, creek, and the property while you stay in a peaceful cabin in the woods! Check out our other listing too if you have a large group and would like to book both rentals. Bourbon Country Cottage

Family · Location · Wifi

Hilltop Retreat-Bourbon Trail-Pool w/Slide-Hot Tub

Relax with the whole family at our newly remodeled home with modern finishes in a secluded country setting. Just minutes from the distilleries, downtown Bardstown, Taylorsville Lake, Keeneland, Lexington, Churchill Downs and Louisville makes this the perfect location for enjoying some of the best that KY has to offer. After a long day of tours and tastings come soak in the hot tub or sit around the fire enjoying the hilltop country views.

Family · Value · Bathroom

Bourbon Trail Log Cabin* Hot Tub* Pond & Speakeasy

Welcome to Bourbon Country Reserve - a luxury log cabin right ON the KY Bourbon Trail. This newly renovated home has a speakeasy lounge with a pool table and custom bar. Sip world-class bourbons hanging around the fire table, fish off the pier, relax in the hot tub while the sun sets, and then roast s'mores! This cabin is perfectly situated for the top distilleries and world class horse racing!

Family · Location · Decor