House holiday rentals in Lebanon

4.98 out of 5 average rating, 134 reviews

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.

Home in Springfield

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!

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, 117 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, 265 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, 232 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.

Home in Washington County

4.99 out of 5 average rating, 178 reviews

Bourbon Trail Summer POOL-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! Amenities include a newly constructed fenced in Inground Pool(open April-October), WiFi/DirecTV, Pool Table, Ping Pong Table, and Golden Tee Arcade Machine!

The game room features a poker table surrounded by comfortable chairs, accented by modern lighting. An outdoor hot tub is enclosed by a wooden deck, inviting relaxation. A fire pit area with several Adirondack chairs presents a cozy gathering spot. A billiards table is positioned under stylish light fixtures.

4.97 out of 5 average rating, 110 reviews

Bourbon Basecamp: 1.5 Acres, Game + Movie Room 3BR

Welcome to Bourbon Basecamp! This home is nestled on 1.5 acres in the Kentucky countryside 12 minutes from downtown Bardstown, the Bourbon Capital of the World! Sleeping up to 6 guests, this luxurious space offers unparalleled comfort, amenities, and the perfect location for you to enjoy the best the bourbon trail has to offer. Conveniently located within 25 miles of +10 distilleries, including Heaven Hill, Maker's Mark and Jim Beam. An hour drive to Louisville, Lexington and Mammoth Caves.

4.96 out of 5 average rating, 111 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 showcases a sectional sofa adorned with yellow accent pillows. A wooden coffee table sits atop a striped rug, while a mounted TV and an electric fireplace provide modern comforts. Natural light enters through the large windows, enhancing the inviting atmosphere.

5 out of 5 average rating, 109 reviews

Bluegrass and Bourbon - Peace on the Bourbon Trail

Retreat to your peaceful hangout after a day of exploring all that Bardstown and KY have to offer! Relax by the fireplace and stream a movie on the 75" TV, cook a full meal in the well-stocked kitchen, create a unique cocktail with all the tools you could wish for, breathe fresh air on the screened-in porch that borders greenspace, challenge friends to poker in the game room, grill dinner on our charcoal grill, or roast hot dogs and s'mores on the firepit area. This must be the place.

A well-set dining table features a wooden surface with a colorful woven placemat displaying a pie in the center. Surrounding the pie are white plates, blue napkins, and flatware. A vase of bright orange flowers adds a touch of color, complemented by a softly glowing candle.

4.89 out of 5 average rating, 271 reviews

Cozy House w/ Sunroom! Sleeps 11 *NO CLEANING FEE*

Incredibly cozy house for your stay! House has three bedrooms, all outfitted with new queen beds! Also included are two roll-away twin memory foam sleepers if needed, along with three sofas that flip down into futons. Great vibe and comfort! Property has a sunroom with a beautiful view. In the sunroom is a spacious table for dinner with a view if you'd like to eat outside. The living room has a 51" tv and wifi. If you have any streaming services you can log in and use them as well!

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.

4.94 out of 5 average rating, 134 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!

4.99 out of 5 average rating, 179 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!

4.97 out of 5 average rating, 194 reviews

A comfortable living room showcases a mix of upholstered furniture, including a plaid sofa and recliners. Natural light enters through the dressed windows, highlighting wooden floors. A coffee table rests in the center, and decorative lamps provide ambient lighting.

Home in Lebanon

Downtown Abode Your home away from home.

No cleaning fee ,Beautiful home in downtown Lebanon a prime location for visiting many locations on the Bourbon Trail or the Lincoln Heritage Trail. We are 60 miles from Louisville or Lexington and only 15 miles from Historic Makers Mark Distilery. Several of our guests have stated the downtown abode is the best Airbnb they have ever stayed in. As a added bonus we have no cleaning fee

Popular amenities for house rentals in Lebanon

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.92 out of 5 average rating, 62 reviews

A charming cottage is positioned on a wooded ridge, featuring a welcoming front porch. Lush landscaping includes well-maintained bushes and small shrubs. Large windows provide ample natural light. The tranquil surroundings complement the serene atmosphere of the property.

Home in Taylorsville

Bourbon Trail Lake Home w/ Hot tub & King Bed

5 out of 5 average rating, 82 reviews

An inviting outdoor space features a spacious in-ground pool surrounded by a decorative fence. Lush green trees provide shade, while the backdrop showcases a sunset sky with soft purple hues. Comfortable lounge chairs are positioned near the water, enhancing the area's relaxing ambiance.

Home in Mount Washington

Pool*Pickleball Bldg*HotTub*Speakeasy*BourbonTrail

4.92 out of 5 average rating, 25 reviews

Bourbon Retreat • Hot Tub + Game

4.97 out of 5 average rating, 29 reviews

An aerial view of the estate captures the expansive grounds, highlighting the beautifully landscaped yard with a saltwater pool, hot tub, and covered gazebo. Pathways illuminated by lights guide the eye towards the house, emphasizing the harmonious blend of luxury and nature.

Home in Bloomfield

Triple Crown Estate | Bourbon Room | Spa | Pool

Superhost

A vibrant sunset casts hues of orange, pink, and purple across the lake, reflecting beautifully on the water's surface. The silhouette of trees and distant houses can be seen against the twilight sky, enhancing the tranquil atmosphere of the scene.

Home in Shepherdsville

4.4 out of 5 average rating, 5 reviews

Sunsets on Bourbon Street! Waterfront views!

4.93 out of 5 average rating, 113 reviews

The exterior of a two-story home is visible, featuring a light grey facade with a front porch and a balcony. Stairs lead up to the porch, surrounded by a well-maintained lawn and shrubs. Nearby houses are visible, set against a clear blue sky.

Home in Taylorsville

Ridge Retreat 42 Sleeps 8 + Crib. NEW HOT TUB

4.8 out of 5 average rating, 59 reviews

The exterior of a charming lakeside cottage is highlighted, featuring a staircase leading to a covered porch. The surrounding yard is landscaped with shrubs and trees, providing a natural ambiance. The cottage is set within a peaceful and green environment.

Home in Taylorsville

Whiskey River Lake Retreat

4.95 out of 5 average rating, 84 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

Weekly house rentals

4.93 out of 5 average rating, 60 reviews

A cozy living area features two olive green sofas adorned with decorative pillows. A coffee table sits at the center, accompanied by a basket of throws. A large artwork of a rooster hangs on the wall, alongside nature-themed prints. Soft lighting is provided by table lamps.

Home in Columbia

Abells Spring Branch

5 out of 5 average rating, 22 reviews

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.

Home in Springfield

BRBN Trail Treehouse FUN-ZONE! Secluded Getaway!

5 out of 5 average rating, 23 reviews

The cottage exterior features a covered porch with a dark bench and decorative mum plants. Large windows allow natural light into the space, while the metal roof provides durability. A spacious lawn extends, revealing open pasture land in the background.

Home in Knifley

Haney’s Hideaway close to Green River Lake

The exterior of Foster Lodge is showcased, featuring a charming brick facade under a partly cloudy sky. Surrounding landscaping includes manicured grass and several trees, with autumn leaves providing a seasonal touch. A walkway leads to the front entrance, enhancing the inviting appearance of the home.

5 out of 5 average rating, 90 reviews

Foster Lodge at Green River Lake - Pet Friendly

5 out of 5 average rating, 32 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, 34 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

Superhost

Home in Liberty

5 out of 5 average rating, 3 reviews

Welcome to the holly house, a quiet retreat!

5 out of 5 average rating, 45 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 Dog Friendly Farmhouse in Harrodsburg

Private house rentals

A charming farmhouse features a Bedford stone exterior and pitched roof. The front porch is highlighted by a welcoming entrance, surrounded by greenery and flower pots. In the background, silos and farm structures are visible, set against a soft evening sky.

5 out of 5 average rating, 48 reviews

Farmhouse/25 mins to E-town/45 mins to Louisville

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, 19 reviews

Three Bedroom Country Cottage

4.9 out of 5 average rating, 30 reviews

Cozy Two Bedroom Retreat

Superhost

Home in Lawrenceburg

5 out of 5 average rating, 4 reviews

Sip, Soak & Stay | Bourbon Trail Lakehouse Gem

4.92 out of 5 average rating, 25 reviews

The dining room features a wooden table surrounded by black spindle-back chairs. A sideboard displays decorative candles and a bowl of fruit. Two portraits adorn the walls, complemented by a chandelier overhead. The room opens to a doorway leading to other areas of the home.

Home in Bloomfield

The Clayborn House

5 out of 5 average rating, 12 reviews

Home in Lawrenceburg

Keeneland, distilleries this cozy place is close.

A spacious living area features a sectional sofa facing a wall-mounted television. A bright yellow coffee table contrasts with the dark furnishings. The dining area, visible in the background, includes a long table with multiple chairs. A staircase leads to the upper level, adorned with a decorative sun motif.

5 out of 5 average rating, 10 reviews

Distillers Den Hottub, Air Hockey/net, Bar, Bags

The exterior of a charming brick home is displayed, featuring a peaked roof and symmetrical windows with black shutters. A small set of steps leads to the front door, flanked by trimmed shrubs, with a spacious lawn providing an inviting front yard.