Family-friendly holiday rentals in Bardstown

A bright living area features a beige couch, complemented by a striking pink wall adorned with a bird mural. A wooden table sits atop a bold red rug, while large windows allow natural light to illuminate the space, enhancing the clean, open layout.

4.99 out of 5 average rating, 154 reviews

Historic Home with Secret Speakeasy right Downtown

The best that Bardstown has to offer! This beautiful, historic, art deco gem is right, smack dab, downtown. The coolest part? Somewhere in the house, behind a hidden bookcase door, you’ll find a secret speakeasy with a beautiful bar setup. One block from the best food, two blocks from the Museum of Whiskey History, and around the corner from all the best bars. Easily the most memorable spot in Bardstown. 10+ distilleries within 10-20 min including Heaven Hill, Bardstown Bourbon and Jim Beam.

4.86 out of 5 average rating, 159 reviews

A cozy living area is presented, featuring a blue sofa and an orange chair. A wooden coffee table, adorned with books, sits in front of a large TV. The space opens to a bedroom area with a king-size bed, framed by soft drapery.

Guest suite in Bardstown

Bourbon Basement

This charming retreat offers the perfect blend of convenience and comfort, putting you right in the heart of it all. Located within walking distance of local restaurants and boutique shops, it's easy to explore the best the area has to offer. Plus, with several renowned distilleries just a short drive away and Louisville only 45 minutes from your doorstep, bourbon lovers will find endless opportunities for adventure. Enjoy the privacy of your own entrance and the ease of parking just steps away.

4.9 out of 5 average rating, 115 reviews

A spacious kitchenette area is highlighted by a large wooden dining table with four chairs. A vibrant mural reading 'The Bed & Bourbon' enhances the room's character. The kitchen features white cabinetry and modern appliances, creating a functional space for meal preparation.

Apartment in Bardstown

Bed and Bourbon on 3rd

Want to have all the necessities, but also be right in the center of all the action? Check us out, located in an upstairs loft on the Main Street in Bardstown! Minutes from over 15 distilleries, a few hundred feet from the circle in town, on the Main Street, with tons of great restaurants, bars, tours, and local shops! This Bourbon inspired loft features a kitchenette, large open living/dining space, a bedroom with a queen, and a chaise bed and a seating area. All of this with views of the town!

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, 118 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

Farm stay in Elizabethtown

4.99 out of 5 average rating, 136 reviews

Mini Cow Cottage! Peaceful Farm Getaway

Come enjoy this peaceful private getaway in a beautiful country setting that is still close to town and the bourbon trail. The cottage offers two bedrooms (one king, one queen) and one bath with an open floor plan, fully stocked kitchen, W/D, front and back covered porches, and don't forget the animals! We have mini Highland and High Park cattle, a horse, friendly barn cats, and spacious natural surroundings. There is also a walking trail along the woods, and a beautiful pond. Dogs welcome too!

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, 234 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.

4.99 out of 5 average rating, 450 reviews

The charming yellow cottage features a covered front porch with two black chairs, inviting relaxation. Neatly trimmed hedges line the walkway, leading up to the front door, which is adorned with a decorative wreath. A spacious lawn and a clear blue sky enhance the warm appearance.

Cottage in Bardstown

The Cottage Circa 1898 Downtown Location

Charming 1800's cottage listed on the National Register of Historic Places in Bardstown. Voted Most Beautiful Small Town in America. Walking distance from downtown shopping, nightlife, dining, and local attractions. Located along the Kentucky Bourbon Trail. I love Bardstown and wanted my cottage to look and feel like what is best about the town- historical charm mixed with modern amenities. Clean, cozy and comfortable; it is a space that I hope you find enjoyable while visiting Bardstown.

4.98 out of 5 average rating, 281 reviews

The exterior of the stone cabin is framed by lush greenery and flowering plants. Sunlight casts soft shadows across the textured stone walls. A decorative statue stands on a pedestal near the entrance, complementing the natural surroundings.

Cabin in Louisville

Historic Cabin by Bourbon Trail

Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

4.99 out of 5 average rating, 240 reviews

A cozy family room features comfortable seating with a flat-screen television and decorative wall art. An outdoor patio showcases porch swings and hanging plants, bordered by greenery. The bedroom includes a spacious bed and wooden furniture. A fire pit set in the backyard is surrounded by trees.

Guest suite in Bardstown

BourbonCityBnB -1000 sq ft, fire pit, privacy

PRIVATE walkout basement. Walk to downtown. PRIVATE coded entrance, self checkin, over 1000 sq ft, semi-private back yard, fire pit and porch swings. Located in residential area between 1792 and Heaven Hill distilleries. No third party bookings. No pets. 1 bedroom w queen bed, 1 bath w shower, washer/dryer, and family room. Ideally suited for couple or solo traveler. Please message if more than 2 prior to booking. Wet bar, massage table, ice maker, touring bicycles, off street parking.

A cozy living room showcases a comfortable dark sofa and an inviting loveseat. A television is mounted on the wall across from the seating. Wooden accents, including a small table set, add charm. Natural light filters through a window, illuminating the warm wood flooring.

4.92 out of 5 average rating, 131 reviews

Barton House - Long Stays Welcome!

Welcome to the Barton House - your home away from home near the Bourbon trail, wineries, and more! The Barton house gets its name from its close proximity to the Barton 1792 distillery & view of Barton rickhouses from the front door. The house sits in a quiet neighborhood & is a 5 min. drive to the dinner train and quaint streets of downtown Bardstown. It is a short 10 min. drive to many of the distilleries and wineries. Celebrating something special or a special occasion? Let us know!

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, 135 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!

4.98 out of 5 average rating, 232 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.

Popular amenities for Bardstown family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 226 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/ Fireplace & Hot Tub

A charming two-bedroom cottage is displayed, featuring a combination of gray siding and a peaked roof. The front porch is accessible via a small set of steps, surrounded by manicured grass and shrubs. Nearby trees provide a touch of greenery against a clear blue sky.

4.91 out of 5 average rating, 140 reviews

Best view of the lake two bed two bath cottage #4

4.98 out of 5 average rating, 132 reviews

A welcoming exterior view of a stylish house features a covered front porch with seating and decorative elements. The spacious interior showcases a cozy living area with comfortable seating and art on the walls. A well-maintained outdoor space includes a putting green. Natural light brightens the rooms.

Home in Jeffersonville

Walking Bridge, Putt Putt House

4.98 out of 5 average rating, 143 reviews

Two wooden Adirondack chairs are positioned around a stoned fire pit, overlooking a tranquil lake. The scene features lush greenery and a group of ducks gently swimming in the water, complemented by a boathouse and kayaks in the background.

Cabin in Lawrenceburg

Bourbon Trail Bliss by the Lake, HotTub, Kayaks

Home in Washington County

4.99 out of 5 average rating, 179 reviews

Bourbon Trail Summer POOL-ZONE! GameRm! Fish!

4.95 out of 5 average rating, 213 reviews

Luxury Retreat with Hot Tub

4.94 out of 5 average rating, 111 reviews

A circular fire pit area is surrounded by six blue Adirondack chairs, positioned on a green lawn. The cabin, featuring a green metal roof and wooden exterior, is visible in the background among tall trees and open space.

Cabin in Shelbyville

Cabin with spectacular views, creek, & hot tub

The cottage features a two-story structure with a light gray exterior and a welcoming entrance. A front staircase leads to a covered porch area, framed by well-maintained shrubs and greenery. Large windows provide natural light to the inviting living spaces within.

4.9 out of 5 average rating, 146 reviews

Lake Refuge near Louisville & Bourbon Trail #52

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 114 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

4.98 out of 5 average rating, 678 reviews

An elegant two-story white barn structure is set against a blue sky dotted with clouds. A prominent cupola with a weather vane crowns the roof. Trimmed bushes and small trees flank the sides, adding greenery to the scenic rural landscape.

Farm stay in Springfield

The Getaway in Bourbon Country with Breakfast

4.74 out of 5 average rating, 331 reviews

The exterior of a historic red home features a distinct black-trimmed door and a green roof. A garden of blooming daffodils surrounds the base, providing a vibrant contrast to the building, while a wooden fence encapsulates the property, enhancing the charm of the setting.

Cottage in Bardstown

Bourbon Oak Smokehouse Cottage

4.96 out of 5 average rating, 236 reviews

A restored farmhouse is shown with a charming white exterior and a black roof. The front porch features white railings, while the surrounding lawn is well-maintained with a grassy area and some trees in the background.

Chalet in Lawrenceburg

Countryside On the Bourbon Trail, 22 Quiet Acres

4.97 out of 5 average rating, 199 reviews

The exterior of a large farmhouse is depicted, surrounded by lush green grass and vibrant flower beds. A blooming pink dogwood tree provides shade in the front yard. The porch features colorful chairs, and elements of country decor, including a decorative star, are visible.

Farm stay in Lebanon

Farmhouse in the Country

4.9 out of 5 average rating, 174 reviews

An open-concept apartment features a kitchen island with seating for four, surrounded by bright yellow walls. Natural light highlights the living area, where comfortable seating is arranged. Decorative elements, including framed artwork and potted plants, enhance the inviting atmosphere.

Farm stay in Raywick

Adorable one bedroom w/ fireplace. Bourbon trail

4.96 out of 5 average rating, 121 reviews

The exterior of a brick patio home is showcased, featuring a well-maintained landscape with shrubs lining the entrance. A one-car garage is visible, with a paved walkway leading to the front door. Trees are present in the background, and autumn leaves cover the ground.

Home in Shepherdsville

WynDown Spot

4.98 out of 5 average rating, 127 reviews

A spacious studio features an industrial design with exposed brick and weathered walls. A cozy Queen Murphy Bed is dressed in neutral linens and accented with decorative pillows. A stylish plant adds a touch of greenery, while well-placed lighting creates a warm ambiance.

Apartment in Shelbyville

Unique Downtown Studio with an Industrial Vibe

Family-friendly home rentals with a pool

Guest suite in Louisville

4.96 out of 5 average rating, 395 reviews

Cherokee Park Oasis with Pool and Hot Tub

Apartment in Central Business District

A resort-style pool area is surrounded by lounge chairs, featuring a separate hot tub nearby. The pool is framed by landscaped greenery and a contemporary building exterior, with multiple balconies visible in the background.

4.89 out of 5 average rating, 295 reviews

4th Street Suites - Luxury King Bed Suite

4.95 out of 5 average rating, 152 reviews

Two horses are depicted, one dark brown and the other light chestnut, standing side by side. They are adorned with riding gear, their eyes focused on the landscape ahead, which features rolling hills blanketed in greenery and autumn foliage.

Farm stay in Harrodsburg

The Bunkhouse at Big Red Stables

5 out of 5 average rating, 123 reviews

An outdoor seating area is displayed, featuring two white armchairs and a stone-top coffee table, arranged on a green and white striped rug. String lights illuminate the space, which is bordered by tall green shrubs and a wooden fence.

Home in Prospect

Top 1%• Yard + Porch • 3BR • Peppermint Cottage

4.94 out of 5 average rating, 232 reviews

The exterior of a spacious carriage house is shown, featuring a stone facade and a grey roof. Three garage doors are visible, along with multiple windows framed in green shutters. A large tree provides shade to the front porch, which invites a sense of coming home.

Cottage in Shelbyville

Cozy Cottage on Firefly Farm

Apartment in Central Business District

A light-filled living area features a comfortable sofa adorned with soft throw pillows and a cozy blanket. A modern coffee table displays a decorative arrangement of flowers, while a colorful artwork of a tree enhances the inviting atmosphere. Large windows provide views of the surrounding buildings.

4.96 out of 5 average rating, 152 reviews

Stylish DT Apt • King Bed, Gym, Pool + Hot Tub

A two-story cottage with light gray siding and a symmetrical facade is shown. The front porch features wooden steps leading to an inviting entrance. Lush green hedges frame the exterior, while a gravel driveway extends to the left, emphasizing the cottage's serene setting.

4.83 out of 5 average rating, 120 reviews

Lake Livin' & Bourbon Sippin'