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Vacation rentals in Shepherdsville

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Top-rated vacation rentals in Shepherdsville

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Top guest favorite

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

4.98 out of 5 average rating, 112 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!

Top guest favorite

A cozy bedroom features a spacious bed with crisp white linens and decorative pillows. Above the bed, a vibrant artwork of a cow adds a touch of character to the room. A bedside lamp and a small blue nightstand provide additional comfort.

Place to stay in Vine Grove

4.99 out of 5 average rating, 141 reviews

Fort 5400

Rustic 1 bedroom unit on 6 acres. Beautiful creek a couple hundred yards from your door with lovely sunsets. Vaulted living room, dual reclining sofa, 50 inch ROKU TV & dinette. Kitchenette with full size refrigerator, microwave, and Keurig coffee maker. King size bed, cozy electric fireplace, 32 inch ROKU TV and closet with washer/dryer. The grounds are shared with one other tenant. FT Knox-6.2 Miles Elizabethtown Sports Park-15 miles Church Hill Downs-36 miles Boundary Oak Distillary-7 miles

Top guest favorite

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

5 out of 5 average rating, 235 reviews

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.

Top guest favorite

A comfortable living area features a brown leather sofa adorned with plaid cushions, accompanied by a light-colored armchair. A round coffee table rests on a patterned rug, displaying magazines. Indoor plants and a decorative lamp add a touch of greenery and light to the space.

Farm stay in Loretto

4.99 out of 5 average rating, 484 reviews

The Barrel Head

* LOCATED RIGHT ON THE BOURBON TRAIL * At the Barrel Head bed, we strive to make our guest feel as comfortable as possible. This location has been newly remodeled and furnished; a brand new queen size bed, pull out sofa, and coffee bar ensure that you are getting the sleep and energy you need for all of your endeavors while staying on the Bourbon Trail. The Barrel Head is also handicap accessible. There are not any steps, and we have installed a walk in shower for anyone in a wheel chair.

The exterior of a brick building is visible, featuring large windows that display items inside. A streetlamp stands nearby, and a blue vehicle is parked along the curb. The surrounding area includes adjacent buildings and trees, contributing to the urban setting.

Apartment in Bardstown

4.73 out of 5 average rating, 770 reviews

The Honey Hole Loft

Nice OLDER Apt. while I think it has charm this building was buiIt in 1900 and the walls and parts of the loft are old in this 1 Bedroom, 1 Bath with Laundry Room in Bathroom. Has a Couch and Futon in the Den. Nice Large Bathroom with Shower and Tub. Full Nice Kitchen. Nice Deck with Beautiful Downtown View. Someone could sleep on the couch, but this is more definitely more suitable for 2 people. A honey hole (or honeyhole) is slang for a location that yields a valued commodity.

Top guest favorite

A wooden deck leads to the entrance of the cottage, surrounded by lush greenery. A concrete patio features a circular table with benches, providing a shaded outdoor space. The natural setting creates a serene environment, with trees framing the view.

Cottage in Hodgenville

4.98 out of 5 average rating, 219 reviews

Basil Cottage on the Creek

The Basil (baz-el) cottage is the perfect get-a-way where you can sit on the back porch sipping coffee while overlooking the babbling creek- get back in touch with nature for a much needed break from the stress of every day life. It may be a much needed romantic weekend, a mid- way point as you tour the bourbon trail, visiting Lincoln's childhood home or just a place of your own while in town to visit family, no matter what brings you to our cottage- you will love it here.

A spacious sleeping area features a king bed with a soft beige quilt and matching pillows. Two bedside lamps provide warm lighting beside wooden nightstands. The ceiling is accented by textured panels, and the cozy carpet extends across the floor.

Place to stay in Shepherdsville

4.88 out of 5 average rating, 308 reviews

A Little Bit of Kentucky

A unique loft apartment near Louisville, Bardstown and just across the river from Indiana. This is attached to our Wedding venue for the convenience of anyone who is coming in for a wedding. It has its on separate entrance away from the venue so you wont be bothered by anyone. We are more than willing to accommodate you in any way we can. Let us know what you need and we will do our best to meet your needs. Check our guide book for local attractions and mileage

Condo in East Market District

4.92 out of 5 average rating, 147 reviews

Perfect Nulu Getaway w/ Best Location- low fees

You can’t find a better location in the city. Welcome to Lou Lou on Washington, our Nulu condo. We are located just steps away from the best food, drinks, and events in the derby city. We are located on a quiet street, only one block away from Main St. You can walk to breweries next door or even a soccer game at Lynn Family Stadium. The Yum Center is only a few blocks away, and we have one of the few properties located walking distance from Waterfront Park.

Top guest favorite

A cozy living area is furnished with a spacious sectional couch and a leather armchair. A wooden coffee table holds magazines. Light-colored walls are complemented by framed artwork, and a pass-through window connects to the kitchenette area.

Guest suite in Coxs Creek

4.99 out of 5 average rating, 210 reviews

★Jenny's Place - Basement Suite, Private Entrance★

Welcome to Kentucky & Bourbon Country! Jenny's Place includes your own private lower-level walkout suite, with all the amenities, nestled in a quiet subdivision. We are centrally located near many events and activities, including the Bourbon Trail, Four Roses Bottling (5 min away), Jim Beam Distillery (10 min away) and Bernheim Forest (10 min away). We are conveniently located 15 minutes from Bardstown, the Most Beautiful Small Town in America. Come see us!

The cottage is nestled among lush greenery, showcasing a unique design with corrugated metal and concrete. A wooden deck leads to the entrance, surrounded by neatly arranged flower beds. Windows provide ample natural light while blending harmoniously with the woodland surroundings.

Cottage in Coxs Creek

4.96 out of 5 average rating, 146 reviews

Bourbon Way Cottage

Unique cottage nestled in the woods located along the Bourbon Trail. Centrally located near miles of nature trails in Bernheim Forest & many of the distillery tours. Yet lots of privacy on 10 wooded acers. 8 minutes to Jim Beam Distillery, 8 min to Bernheim Forest, 4 min to Four Roses Bourbon Warehouse & Bottling Tour, 12 min to the City of Bardstown, 30 min to Churchill Downs, 26 min to Louisville International Airport (SDF) NO SMOKING NO PETS

Top guest favorite

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

4.96 out of 5 average rating, 100 reviews

WynDown off the Bourbon Trail

Wind down at this centrally located patio home that comes with an attached garage. This wine-themed home is open and airy, and has a screened-in patio for guests to enjoy. Located 0.2 miles from I-65 and minutes away from grocery stores and restaurants. Forest Edge Winery, James Beam Distillery, and MillaNova Winery are a 10-15 minute drive and many other attractions are nearby. You and your pets can "wine down" at Wyandot!

Top guest favorite

A inviting studio space features a spacious bed dressed in white linens, accompanied by a wooden nightstand. A blue sofa and a red armchair provide comfortable seating options. A flat-screen TV is positioned on a media console, enhancing the cozy atmosphere of the room.

Apartment in Mount Washington

4.95 out of 5 average rating, 206 reviews

“Crossroads” connecting Louisville and Bardstown

This apartment is good for couples, solo adventurer and business travelers. It is 10 miles south of Louisville, 18 miles north of Bardstown, 18 miles west of Taylorsville Lake and 1 hr away from Lexington. It is close to a very cool park, The Parklands, where you can hike, bike and kayak. The apartment is centrally located in the “crossroads” of several really cool communities in horse country, Kentucky.

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Popular amenities for Shepherdsville vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Shepherdsville

A charming farmhouse is situated on a grassy lawn, surrounded by trees. An American flag is displayed in the front yard. The home features a welcoming front porch and a large attached garage, blending beautifully with the natural surroundings.

Home in Lebanon Junction

4.92 out of 5 average rating, 48 reviews

Happy Goose Hollow

Top guest favorite

The living room features a leather sofa paired with an accent chair, situated around a circular coffee table on a soft area rug. A wall-mounted TV is present, along with decorative shelves displaying plants and decor items. Natural light enters through large windows, complemented by curtains.

Home in Shepherdsville

4.98 out of 5 average rating, 82 reviews

The Dark Horse Inn *Derby Dream House*

Top guest favorite

A gravel driveway leads to the entrance of a single-story building with a red metal roof. Surrounding greenery and a few trees create a tranquil setting. A traditional red barn is visible in the background, adding to the rural atmosphere.

Farm stay in West Point

5 out of 5 average rating, 39 reviews

Love's Touch at R Applegate Farm

Top guest favorite

An open studio apartment features a spacious layout with a wooden bed frame and a single bed. Soft light filters through multiple windows, illuminating a cozy seating area with patterned chairs and a round coffee table. Decorative elements add a touch of comfort.

Apartment in Louisville

5 out of 5 average rating, 51 reviews

Cozy Garage Apt- Country Charm with City Amenities

Top guest favorite

A cozy outdoor seating area features a glass-top table with two filled wine glasses, a small potted plant, and a decorative pillow on the couch. Warm lighting enhances the relaxing ambiance, inviting guests to enjoy the surroundings.

Home in Mount Washington

5 out of 5 average rating, 34 reviews

The Bourbon Trail Bungalow Ping pong/Foosball/Bar

Top guest favorite

The open-concept living area features high, wooden beams and a combination of rustic and modern decor. A spacious kitchen island is accompanied by stools, while a cozy seating area includes a sofa and armchairs. Large windows allow natural light to fill the room.

Cabin in West Point

5 out of 5 average rating, 27 reviews

The River View Cabin

Top guest favorite

A serene sunset is captured over rolling hills, where the sun casts warm orange and yellow tones across the sky. Wispy clouds are visible, enhancing the natural beauty of the horizon. The foreground features lush greenery, creating a peaceful ambiance.

Home in Floyds Knobs

4.99 out of 5 average rating, 81 reviews

Home with Breathtaking View

Top guest favorite

A rustic wooden cabin is visible, featuring a covered porch with white railings. The structure stands against a clear blue sky and green hills, complemented by a path lined with a wooden fence leading to the cabin.

Cabin in Lebanon

5 out of 5 average rating, 41 reviews

Shepherd's Rest

Quick stats about vacation rentals in Shepherdsville

Total rentals
30 properties
Nightly prices starting at
ﺩ.ﺇ220 before taxes and fees
Total number of reviews
1.9K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace

Frequently Asked Questions

Are there pet-friendly house rentals in Shepherdsville?
Four-legged friends are welcome in Shepherdsville. Choose from more than 20 house rentals for guests traveling with pets.
What are the most popular amenities for House Rentals in Shepherdsville?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with free parking, over 20 homes with air conditioning, over 20 homes with a kitchen, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Shepherdsville have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Shepherdsville. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Shepherdsville?
Shepherdsville has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there house rentals with a dedicated workspace in Shepherdsville?
Yes! Work meets play with ease at over 10 house rentals in Shepherdsville featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Shepherdsville have free parking?
Absolutely! We offer over 20 house rentals with free parking in Shepherdsville. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Shepherdsville have wifi?
Absolutely! We offer over 20 house rentals with wifi in Shepherdsville. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Shepherdsville have a kitchen?
Absolutely! We offer over 20 house rentals with a kitchen in Shepherdsville. Enjoy a tailored experience with all the comforts you desire.

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