Holiday rentals in Chaplin

4.96 out of 5 average rating, 131 reviews

The image collage features various spaces of a stylish home. A cozy lounge area with a fireplace is shown, alongside an outdoor hot tub surrounded by greenery. The dining area is connected to a deck, and a game room with a bar creates an inviting entertainment space.

Home in Bardstown

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

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4.99 out of 5 average rating, 267 reviews

A rustic cabin is nestled among trees, featuring a well-lit entryway and a front deck with two wooden lounge chairs. Soft evening light spills through the windows, creating a welcoming atmosphere. Stone stepping stones lead towards the doorway, enhancing the natural setting.

Cabin in Lawrenceburg

Romantic Cozy Cabin Getaway w/ Firepit & Hot Tub

*NO smoking property (inside or out)* Privately nestled on over 5 wooded acres & intentionally curated for your stay. Gain access to quiet, immerse yourself in nature, and support your rejuvenation. 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. (Note:18+only)

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Guest house in Springfield

An outdoor gathering space is highlighted, featuring a circular structure with a metal façade. Strings of lights create a warm ambiance against the dusk sky. A large flat-screen television is mounted on the wall, complementing the open seating area with various tables and chairs.

Lofty Lodge on the Bourbon Trail

Come to the Bourbon Trail in the Heart of Kentucky! Stay at our beautiful lodge with large common areas perfect for hanging out! Our space is great for family trips, work retreats, or a couples get away! The lodge is located just 3 miles from from restaurants, groceries, pharmacies and shops. But at the Lodge you will enjoy the peace of the country. We are central to all the bourbon distilleries: 15mi to Maker's mark, 35mi to Jim Beam, 50mi to Woodford Reserve, Lexington and Louisville.

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4.99 out of 5 average rating, 139 reviews

The exterior view showcases a spacious two-story home with a sloped roof and light brick walls. A back patio features dark outdoor seating and overlooks a vast green lawn. Additional trees are visible in the background, enhancing the peaceful countryside setting.

4.97 out of 5 average rating, 39 reviews

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.

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4.92 out of 5 average rating, 38 reviews

Triple Crown Estate | Bourbon Room | Spa | Pool

Your Kentucky Dream Awaits: Kentucky’s Most Spectacular Sunset Views Private Bourbon Tasting Room Private Cinema +Poker Room + Billiard Lounge Stunning 16-ft Ceiling Living Room w/ wraparound sectional, bar & lounge Private Saltwater Pool + 6-Person Hot Tub + Handcrafted Barrel Sauna 6 Private Acres w/ stocked pond & fire pit for 12 ppl, perfectly positioned for sunset magic Grand Dining Deck w/ BBQ, built-in hot tub overlooking the estate Covered Gazebo w/ Bar Just 12 Min from Bardstown

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5.0 out of 5 average rating, 29 reviews

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.

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4.93 out of 5 average rating, 15 reviews

Home in Chaplin

Bourbon Trail Estate | 6BR | Pickleball | Hot Tub

Six bedrooms, five kings, one queen and 4.5 bathrooms. No bunk beds. No pull-out sofas. No short straws. Welcome to Prather Ridge Estate, the Bourbon Trail's ultimate group retreat. 12 guests, 5 private Kentucky acres, hot tub with rolling hill views, infrared sauna, private pickleball court, ping pong, fire pit under string lights, and a Bourbon Lounge for the post-trail pour. Chef's kitchen, open-concept living and dining, perfect for groups. Distilleries, laughter, zero compromises.

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4.95 out of 5 average rating, 123 reviews

A unique circular structure made of wood stands on a wooden deck surrounded by vibrant wildflowers. The entrance features a sliding door, while a small shelf extends from the side, inviting guests to explore the natural setting.

Farm stay in Chaplin

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.

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4.99 out of 5 average rating, 197 reviews

An open living area showcases comfortable seating arranged around a neutral rug. Modern kitchen appliances are visible in the background, complemented by dark wood cabinetry. Natural light enters through the window treatments, enhancing the inviting space. A welcoming entrance is seen to the left.

Home in Springfield

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!

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4.98 out of 5 average rating, 263 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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4.94 out of 5 average rating, 468 reviews

A charming log cabin is surrounded by lush greenery, featuring a porch with rustic wooden railings. A brick chimney rises from the side, complementing the gabled roof. The outdoor area includes a pathway leading to the cabin, set amidst the serene woodland landscape.

Cabin in Mount Eden

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

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