Vacation rentals in Shepherdsville

4.98 out of 5 average rating, 107 reviews

A charming brick home with a welcoming front porch is situated under a large tree. Lush green grass surrounds the property, and the sky showcases soft hues of pink and purple, creating a serene backdrop. The house features multiple windows and a prominent chimney.

Home in Boston

Ginger's Blissful Acres

Enjoy peace and quiet in the country! A quick 10 minute drive to downtown Bardstown. 1750 sq ft home on 50 acres. The property has been in the family since 1902. Great for families, couples and motorcycle riders! Enjoy a full kitchen, grill and fire pit with wood. Parking right outside the back door. Centrally located on the Bourbon Trail and close to Bernheim Forest, My Old Ky Home, Mammoth Cave, Kentucky Railway Museum, antique shops, Lincoln's birthplace, Fort Knox, museums and many others.

Place to stay in Vine Grove

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.

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

Guesthouse in Elizabethtown

An open living area features a spacious sectional sofa arranged around a decorative area rug. Warm wood ceilings complement the neutral tones of the furniture. The kitchen and dining area are visible in the background, providing a seamless flow between spaces.

5 out of 5 average rating, 35 reviews

Beautiful view, private lake, game room!

Bring the whole family to this private country getaway. With 2500 sq ft of living space and 7 total acres you’ll have plenty of space to explore! Of those 7 acres, 3 of them are a private lake great for fishing, swimming or a paddle boat. This “guesthouse” is the finished basement of the house we live in. These are 2 completely separate spaces with their own entrances. We live in the upstairs and offer our 2500 sq ft finished basement with its own living room, kitchen, game room & 2 bedrooms.

4.99 out of 5 average rating, 240 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.

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.

4.93 out of 5 average rating, 56 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.

5 out of 5 average rating, 18 reviews

Apartment in Brooks

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.

4.96 out of 5 average rating, 147 reviews

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

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

4.91 out of 5 average rating, 311 reviews

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

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.

Guest suite in Louisville

The inviting bedroom features a spacious bed with white linens and a soft green throw. A mounted projector is positioned on the ceiling, with greenery-patterned wallpaper creating a serene ambiance. Two bedside tables with lamps and a bench at the foot of the bed enhance functionality.

4.99 out of 5 average rating, 208 reviews

Olive Branch Suite with projector screen in E Lou

This suite is a beautiful private retreat complete with a projector for watching your favorite streaming service for the ultimate movie night. Centrally located and within 10-20 minutes of numerous local hospitals, universities, as well as various restaurants and downtown destinations, our guest suite offers a peaceful retreat in a convenient and safe location. We also provide a fold out desk that guests can use for a remote work space if desired.

4.98 out of 5 average rating, 191 reviews

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

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.

4.99 out of 5 average rating, 161 reviews

The exterior of the tiny house features a warm wood and shingle design. A welcoming red door is flanked by large windows. A wooden deck leads to steps adorned with potted mums, pumpkins, and gourds, while outdoor seating is visible for enjoying the surroundings.

Tiny home in Loretto

Shot Glass Tiny House, 3 miles to Maker’s Mark

This is what you call glamping! Get away from it all when you stay under the stars at the Shot Glass Tiny House on wheels located at the end of a backroad surrounded by nature with a small stream out front approximately 3 miles from Maker’s Mark. You will be able to observe wildlife through the big picture window out front and surrounding windows throughout while staying comfortable as you glamp in the rustic style tiny house on wheels .

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.

4.96 out of 5 average rating, 102 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!

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Popular amenities for Shepherdsville vacation rentals

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Pool

Free parking on premises

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Other great vacation rentals in Shepherdsville

Cabin in Lebanon Junction

A rustic log cabin sits amidst lush greenery, featuring a red metal roof and a stone chimney. The screened porch offers a view of the expansive yard, bordered by a rustic wooden fence, while trees and vegetation create a natural setting around the home.

5 out of 5 average rating, 25 reviews

Woodland Oasis: Historic Cabin with Modern Comfort

4.95 out of 5 average rating, 22 reviews

The spacious bedroom features a queen-sized bed dressed in white linens, complemented by a large tufted bench. A plush rug adds warmth to the wooden floor, while exposed brick walls and decorative wall art create visual interest. Soft lighting from a stylish chandelier enhances the overall ambiance.

Apartment in Louisville

Charming 1BR Retreat in the Heart of Louisville!

A spacious outdoor area features a covered porch with seating options, including two lounge chairs and a large hammock. A charcoal grill is positioned nearby on a concrete surface. Lush grass surrounds the structure, providing ample space for outdoor activities.

Guesthouse in Mount Washington

4.78 out of 5 average rating, 436 reviews

Kentucky Derby Guest House

Cabin in Bardstown

5 out of 5 average rating, 6 reviews

Bourbon Country Cabin-Hot Tub, Game Room, Fire Pit

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.

4.98 out of 5 average rating, 84 reviews

The Dark Horse Inn *Derby Dream House*

A welcoming living area is furnished with a plush brown sofa and matching armchair, illuminated by natural light from a window. A wooden coffee table and desk are present, while a plant stand with various greenery adds a touch of nature to the space.

4.93 out of 5 average rating, 15 reviews

Turtle View 1

Cabin in Bloomfield

5 out of 5 average rating, 4 reviews

The Cabins at Brookhaven - The Nest