Vacation rentals in Shepherdsville

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Top-rated vacation rentals in Shepherdsville

Guests agree: these stays are highly rated for location, cleanliness, and more.

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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, 143 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

Guest favorite
A charming log cabin is framed by lush green trees, showcasing a warm exterior with a stone chimney. Rocking chairs are placed on the front porch, surrounded by vibrant flowers and a neatly maintained garden path leading to the entrance.
Cabin in Louisville
4.95 out of 5 average rating, 348 reviews

Captain's Cabin: Bourbon Trail, History & Romance

Your own log cabin on a wooded hillside with gourmet breakfast served to your door (on weekends)! It's been the location for 5 movies, including Lifetime! Period furnishings and modern conveniences make this an unforgettable retreat. A massive stone fireplace creates a quiet ambiance. Watch wildlife by the lake, creek or from back porch swings. Comfy bed, luxury sheets, high-speed internet, bluetooth stereo and special touches make your stay magical! Ask for Cooking With Bourbon Experience.

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
4.99 out of 5 average rating, 241 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.

Guest favorite
The exterior of a single-story brick home features a well-maintained lawn bordered by shrubs. A small front porch with a couple of chairs invites relaxation. The background shows a spacious fenced yard and neighboring houses.
Home in Shepherdsville
4.93 out of 5 average rating, 57 reviews

Modern Comfort •Bourbon Trail & Derby•Fenced yard

Welcome to your perfect Kentucky retreat! Nestled in a peaceful neighborhood, this spacious home offers everything you need for a comfortable stay. Enjoy a fully fenced backyard—ideal for pets and kids—a large back deck with a grill, and a roomy garage and driveway for convenience. Inside, relax on a super-comfy couch in the living room, cook up a feast in the full kitchen, and take advantage of two full bathrooms and a washer/dryer. It’s perfect for families, groups, and pet owners.

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, 224 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.

Guest favorite
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, 312 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

Top guest favorite
Apartment in Brooks
5 out of 5 average rating, 19 reviews

Cozy Studio in Brooks

Step in to a bright and cozy studio apartment with Moroccan flair - only 20minutes from downtown Louisville, Kentucky Kingdom and Churchill Downs, 15 minutes from the SDF airport and Bernheim Forest and 10 minutes from miles of Jefferson Memorial forest trails. Located on a country hillside with a separate entrance and a high outside deck that opens to the treetops, it's the perfect place to relax but still be close to all that Louisville has to offer.

Top guest favorite
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, 147 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

Guest favorite
The sun sets beyond a serene landscape, casting warm orange and golden hues across the treetops. Silhouetted branches add texture to the scene, while the fading light enhances the tranquil atmosphere, showcasing the natural beauty surrounding the cabin.
Cabin in Shepherdsville
4.94 out of 5 average rating, 35 reviews

Bourbon Trail Cabin

Have fun with the whole family at this stylish place. • House is situated at 725' elevation to take advantage of the spectacular panoramic views. • Located in picturesque, unheralded Bullitt County. Did you know? • You can visit 4 award-winning wineries and 2 distilleries on the Wine and Whiskey Trail. • Enjoy the Nation's longest go-cart track • Enjoy target practice at Knob Creek gun range • Visit and Hike at Bernheim Forest. * Prime Hunting areas

Guest favorite
The cabin exterior is constructed with natural wood logs, featuring a metal roof in a deep hue. Windows allow natural light to enter, with a covered porch area to the side. A paved driveway leads to the entrance, surrounded by natural greenery.
Cabin in Elizabethtown
4.91 out of 5 average rating, 312 reviews

The Cabin- private,cozy, firepit, hammock, pacman

Take a break and unwind at this peaceful oasis. Blurring the lines between structure and nature, this cabin retreat inspires a feeling of tranquility. The footprint compacts everything one could need- living, kitchen, bed, bathroom, washer/dryer, games and more. Enjoy the peaceful sounds of nature while napping in the hammock. Cook dinner over an open flame in the firepit. Test your skills to beat the high score on PacMan arcade or the foosball table.

Top guest favorite
An interior view of the geodesic dome features a cozy sleeping area with a king size bed and attractive bedding. A dining table with four brown chairs is positioned nearby. Natural light streams in through the large geometric windows, illuminating the earthy tones of the decor.
Dome in Mount Washington
4.98 out of 5 average rating, 193 reviews

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.

Guest favorite
Home in Shepherdsville
4.89 out of 5 average rating, 74 reviews

Cedar Forest House

Enjoy the location convenience this quaint home has to offer. The Cedar Forest house is a 3 bedroom home located 0.2 miles from the I-65 exit and a short distance to many nearby attractions including bourbon distilleries, wineries, and Bernheim Forest. During your stay, guests can enjoy the two sitting rooms, each with their own smart TV, and stocked with board games. Pets are welcome for an additional pet fee.

Popular amenities for Shepherdsville vacation rentals

Quick stats about vacation rentals in Shepherdsville

  • Total rentals

    30 properties

  • Nightly prices starting at

    G$16,828 GYD before taxes and fees

  • Total number of reviews

    1.8K 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 vacation rentals in Shepherdsville?

    Four-legged friends are welcome in Shepherdsville. Choose from more than 20 vacation 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 wifi, over 20 homes with air conditioning, over 20 homes with free parking, over 20 homes with a kitchen, 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 vacation rentals in Shepherdsville?

    Shepherdsville has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there vacation rentals with a dedicated workspace in Shepherdsville?

    Yes! Work meets play with ease at over 10 vacation 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.