House vacation rentals in Lebanon

The exterior of the home features a charming white façade with black accents, complemented by a small set of steps leading to the front door. Lush green grass surrounds the property, and a gravel pathway is lined with decorative stones and small shrubs.

4.98 out of 5 average rating, 121 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!

5 out of 5 average rating, 190 reviews

A charming farmhouse is visible from across a peaceful pond, surrounded by gently sloping green grass. The house features a wrap-around porch and is framed by trees, creating a serene rural setting. Reflections of the structure and surrounding greenery can be seen on the water's surface.

Home in Raywick

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 for rent across the large driveway that accommodates 2 people as it is a one bedroom with a queen bed. Listed as Bourbon Trail Country Class.

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.

4.96 out of 5 average rating, 105 reviews

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

A charming single-story home features a welcoming front porch with two rocking chairs. Well-maintained landscaping includes shrubs and a gravel pathway leading to the entrance. The exterior showcases a light-colored façade and a gabled roof, surrounded by a grassy yard and neighboring structures.

4.94 out of 5 average rating, 238 reviews

Bardstown Bourbon Bnb - near My Old KY Home

Welcome to our charming Airbnb in Bardstown, Kentucky, the bourbon capital of the world! Situated in the heart of downtown, our spacious and beautifully decorated home is the perfect retreat for bourbon enthusiasts, history buffs, and nature lovers alike. Boasting of three comfortable bedrooms, each furnished with plush bedding. The living area is bright and airy, with large windows and comfortable seating for you to relax. The fully-equipped kitchen is perfect for cooking up delicious meals.

A cozy living area features dark leather sofas and a rustic wooden coffee table. The room is softly illuminated by decorative lamps and small Christmas trees, while framed artwork and wooden accents adorn the walls, creating a warm and inviting space.

4.96 out of 5 average rating, 229 reviews

Bourbon City Retreat

Escape to a Bourbon City retreat In historic Bardstown Ky named “Most Beautiful Small Town In America”. Experience the Bourbon Trail starting where bourbon was born. Visit Jim Beam American Still House, Heaven Hill Bourbon Heritage Center & Four Roses Warehouse just to name a few. Be sure to visit My Old KY Home and My Old KY Dinner Train. Enjoy southern cuisine at Mammy’s Kitchen, Stephen Foster Restaurant & The Rick house. Enjoy your stay in a quiet, clean & cozy home in Bourbon City Decor.

4.96 out of 5 average rating, 226 reviews

Goldenrod Cottage

The Goldenrod Cottage is a cozy one-bedroom, one-bath retreat located on a quiet corner lot with green space next door and peaceful woods across the street. Inside, you’ll enjoy warm hardwood floors, a stocked coffee bar, and all the comforts of home. You are within walking distance of downtown Bardstown, where you can browse unique shops, enjoy live music, and dine at local restaurants. Nearby, you can tour legendary bourbon distilleries, ride the Dinner Train and explore Bernheim Forest.

4.99 out of 5 average rating, 104 reviews

A charming country house is depicted, featuring a red metal roof and a welcoming porch. Two chairs are placed on the porch, overlooking a grassy yard. The backdrop reveals gentle hills under a clear blue sky, creating a serene outdoor setting.

Home in Knifley

The ranch house. Relax and unwind

Quiet, peaceful, country setting. There are country roads for walking and bike riding. For the boaters and fishermen, we are just minutes away from Arnold’s landing boat ramp and also Holmes Bend marina on beautiful Green River lake. For the hunting enthusiast, there are 20,000 plus acres of public land available for spring and fall hunting, with an abundance of turkey and deer. Close to Campbellsville University and Lindsey Wilson in Columbia. Lake Cumberland is also a short drive away.

A spacious living room features a large sectional sofa and a gas fireplace, with a 65" smart TV mounted above the mantle. Natural light floods in through tall windows, while warm wood tones and modern furnishings create a cozy ambiance.

4.95 out of 5 average rating, 113 reviews

Pickleball*Hot tub*Speakeasy*Bourbon*Pet-Friendly

The Bourbon Skyline is your passport to an unforgettable Kentucky experience. This newly renovated 4-bed, 3 full bath ranch sitting on 8 acres is the epitome of comfort and Kentucky charm. The Bourbon Skyline's hilltop location offers beautiful views over Kentucky landscapes. It's the best of both worlds; countryside, & close to everything! Outdoor dining, fire table & hot tub, corn hole and Pickleball! Just a short drive to Louisville, Lexington, Mammoth Cave & so much more!

The historic cottage features a brick exterior highlighted by greenery. Large windows offer natural light, while the entrance is framed by a simple pathway. Surrounding foliage enhances the inviting presence of the home in the heart of downtown Bardstown.

4.91 out of 5 average rating, 337 reviews

The Nicholson Guest House

Stay in a Charming Historic Cottage Experience a piece of history in this beautifully preserved 1830s cottage, located in the heart of downtown Bardstown—just steps from restaurants, shops, markets, local events, and nightlife. As the Bourbon Capital of the World, Bardstown offers many distilleries where you can enjoy tastings and tours of exceptional bourbons. We also offer electric bicycle rentals—perfect for exploring town and beyond. Contact me directly for details.

Home in Washington County

4.99 out of 5 average rating, 174 reviews

Bourbon Trail Pool&Hottub FUN-ZONE! GameRm! Fish!

This two-story country-side home is sure to keep you entertained while also having a relaxing vibe for your getaway. Nestled just off the Bourbon Trail, Makers Mark and historic Bardstown are just a short drive. Proximity to Louisville and Lexington is great too! Sitting on 3 acres, this home Features 4 bedrooms, 2 and a half bathrooms, WiFi/Cable, Pool Table, Ping Pong Table, Golden Tee Arcade Machine, and all amenities. In-ground Pool expected ready by late August!

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.

4.99 out of 5 average rating, 173 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!

The exterior of a two-story Victorian home is presented, featuring white siding and dark shutters. A covered porch with decorative lanterns is flanked by small shrubs and a landscaped lawn. A wheelchair-accessible ramp leads to the entrance, enhancing accessibility.

4.75 out of 5 average rating, 106 reviews

Kentucky Dream on Main

This two-story Victorian abode is a dream getaway, was built in, and is located on the iconic Kentucky Bourbon Trail. With a total of 4 bedrooms, 2 bathrooms, Wi-Fi, and all amenities. This historic home resides right on Main Street in the heart of Springfield Kentucky. This home is perfect for anyone looking to experience historic Kentucky finery with a luxurious, modern design. Guest will be able to check themselves in with a lockbox where they will find a key.

Popular amenities for Lebanon house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A single-story brick house is set within a green lawn, featuring a sloped roof and large front windows. Landscaping includes neatly manicured shrubs and flower beds, providing a welcoming entrance to the home.

4.89 out of 5 average rating, 47 reviews

Beautiful sunrises near Green River Lake NO pets

4.95 out of 5 average rating, 82 reviews

The exterior of a brick cottage is shown, featuring a well-maintained landscape with shrubs and rocks along the pathway. A single entrance door is visible, complemented by a porch area. Trees in the surrounding yard provide shade to the property.

Home in Lebanon

Ticky's Cottage at Empire Estate

An aerial view of The Bluegrass Grand Estate showcases its expansive layout, featuring a circular driveway that leads to the elegant home. Surrounding landscapes include manicured lawns, trees, and a serene pond, while the backyard reveals a swimming pool, stone waterfall, and open fields beyond.

4.69 out of 5 average rating, 13 reviews

The Bluegrass Grand Estate: Bourbon Trail Luxury

5 out of 5 average rating, 4 reviews

Pool*Hot tub*Bardstown

A serene outdoor gathering area features a stone patio surrounded by several black chairs, set beneath a wooden pergola. The farmhouse stands in the background, with the sun setting behind it, illuminating the sky with soft hues.

4.89 out of 5 average rating, 19 reviews

Bourbon Retreat • Hot Tub + Game

4.96 out of 5 average rating, 23 reviews

The exterior of the home is presented, showcasing a ranch-style structure with a gabled roof. A covered porch is visible, adorned with seating. Lush greenery and colorful flowerbeds enhance the surrounding landscape, while clear blue skies provide a bright backdrop.

Home in Liberty

Teddy Hill Homestead

New place to stay

The Rickhouse Retreat Curved Theater Screen • Golf

4.9 out of 5 average rating, 77 reviews

A serene outdoor scene features a sparkling pool surrounded by lush greenery. A vibrant double rainbow arches elegantly across a partly cloudy sky, highlighting the natural beauty of the countryside. Several trees and plants are positioned near the pool area, adding to the tranquil setting.

Home in Mount Sherman

Bourbon trail Oasis, Holiday Home. Inground pool

Weekly house rentals

4.99 out of 5 average rating, 91 reviews

A living area features a dark gray sectional sofa with decorative pillows facing a coffee table atop a soft area rug. A flat-screen television is mounted on the wall, and natural light enters through sheer curtains over the window. An entrance door is visible.

Home in Liberty

Home in Liberty

A cozy living area features two upholstered sofas and a patterned armchair, all arranged around a central coffee table. Natural light fills the space through two windows adorned with light curtains. A welcoming atmosphere is complemented by decorative items on a side table and wall accents.

5 out of 5 average rating, 18 reviews

Three Bedroom Country Cottage

A serene backyard features a seven-person hot tub sheltered under a gazebo, surrounded by privacy curtains. A circular fire pit area contains red lounge chairs, while string lights above create a warm ambiance. Pathways of stone lead through the well-maintained grass.

5 out of 5 average rating, 71 reviews

*NEW*Rhythm & Whiskey- Walk to Bourbon Festival!

A collage of various features showcasing a spacious home and treehouse. A hot tub is visible on the left, while the center highlights a dining area and kitchen. A treehouse sits prominently in the right corner, surrounded by greenery. A fire pit and chairs are positioned outdoors.

5 out of 5 average rating, 21 reviews

BRBN Trail Treehouse FUN-ZONE! Secluded Getaway!

A well-appointed sleeping area features a spacious bed with crisp white bedding, complemented by an orange decorative pillow. A textured dark blanket is laid across the bed. Soft, ambient lighting is provided by bedside lamps, and natural light enters through nearby windows.

4.89 out of 5 average rating, 19 reviews

The Nest

5 out of 5 average rating, 27 reviews

A well-kept, single-story home is set against a backdrop of a clear blue sky and colorful autumn foliage. The house features a welcoming front porch and is surrounded by expansive grassy areas, with a small lake visible nearby.

Home in New Haven

Mom's House

5 out of 5 average rating, 30 reviews

The image captures a spacious brick house set against a bright blue sky dotted with fluffy white clouds. Green grass surrounds the home, and well-maintained shrubs line the front. The property features expansive windows, inviting natural light into the living spaces.

Home in Loretto

Our House is Y'all's House

5 out of 5 average rating, 39 reviews

A charming country farmhouse is visible, featuring a sloped roof and white siding. Green shrubs frame the front porch, which displays flower pots. A neatly manicured lawn surrounds the home, with a pink flowering plant in the foreground. Gray clouds decorate the sky.

Home in Harrodsburg

Charming Pet Friendly Farmhouse in Harrodsburg

Private house rentals

5 out of 5 average rating, 3 reviews

A renovated home with a red metal roof features a cozy outdoor seating area surrounded by greenery. A firepit is surrounded by chairs, and a picnic table is positioned on the lawn. The inviting facade includes well-kept landscaping and a clear sky overhead.

Home in New Hope

The New Hope Bourbon Stop

5 out of 5 average rating, 24 reviews

A modern barndominium structure is featured, showcasing a wooden entryway beneath a sloped roof. Large windows allow for ample natural light, and a lush green landscape surrounds the home, extending toward the horizon under a softly colored sky.

Home in Coxs Creek

Distillery Overlook Barndo Home

4.97 out of 5 average rating, 29 reviews

A one-story farmhouse is shown under a clear blue sky, featuring a light-colored exterior and a metal roof. A wide driveway leads to the carport, with well-maintained greenery surrounding the property and colorful flower beds at the base of the porch.

Home in Greensburg

Hillview Haven

A large painting of a galloping white horse is displayed on the wall. The artwork is rendered in neutral tones with subtle brush strokes, capturing the horse's dynamic movement and flowing mane.

4.83 out of 5 average rating, 30 reviews

Ol Susannah of the Bourbon Trail - 30 DAYS

A spacious living area features a dual reclining loveseat and a comfortable sofa, complemented by a large area rug. Natural light enters through the windows, and a dining table is visible in the background, enhancing the cozy ambiance.

4.96 out of 5 average rating, 49 reviews

Della’s Delight

5 out of 5 average rating, 12 reviews

The exterior of a single-story home features a green metal roof and light beige siding. A wooden deck with steps leads to the front door, flanked by large windows. Trees provide shade on the front lawn, and landscaped areas enhance the entryway.

Home in Elk Horn

Linny’s Landing

A cozy cottage constructed from stone is set against a colorful sunset. The structure features a metal roof, two windows flanking the entrance door, and a well-maintained lawn leading to a gravel driveway.

4.96 out of 5 average rating, 46 reviews

Cozy Lake-house

A finished basement features a foosball table in the foreground and a comfortable seating area with a sofa. A dining table with chairs is positioned nearby, and a television is mounted on the wall, providing entertainment options.