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Vacation rentals in Shepherdsville

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Quick stats about vacation rentals in Shepherdsville

  • Total vacation rentals

    Explore 30 vacation rentals in Shepherdsville

  • Nightly prices starting at

    Shepherdsville vacation rentals start at G$16,733 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,280 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Shepherdsville vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Shepherdsville rentals

  • 4.8 Average rating

    Shepherdsville stays are highly rated by guests—averaging 4.8 out of 5!

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
Cabin in Shepherdsville
4.98 out of 5 average rating, 121 reviews

Bourbon Cabin - Speakeasy/HotTub/Arcade/Derby

🏡 Bourbon Trail Hideaway – A spacious 5BR, 3.5BA log cabin on 6 private acres, just 9 mins from Jim Beam! 🍂 Blending rustic charm with modern comforts, this retreat features a Brand NEW speakeasy lounge, hot tub, fire pit, wraparound decks, arcade games, and a well-stocked kitchen. Enjoy breathtaking sunsets, fast WiFi, plush seating, Smart TVs, and a cozy ambiance, plus luxurious beds, spa-like bath, and plenty of space to relax or entertain. Perfect for groups, couples & bourbon lovers! 🥃✨

Guest favorite
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
4.99 out of 5 average rating, 103 reviews

Pool*Pickleball Bldg*HotTub*Speakeasy*BourbonTrail

Welcome to the "Bourbon Barrel Retreat" where this truly unique property offers a one-of-a-kind getaway. This newly renovated 5-bed, 3 full bath ranch boasts two additional buildings on the property to provide a Kentucky experience like no other. Immerse yourself in the ambiance of the Bourbon Speakeasy or spend time at the Pickleball Sports Lounge. Unwind and relax however you would like! An ideal location where you are a short drive to Bardstown, Louisville, Lexington, Mammoth Cave and more!

Guest favorite
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.
Home in Shepherdsville
4.86 out of 5 average rating, 36 reviews

Turtle View 1

Bring your family, friends, or team to this great place with lots of room for fun. Mohammad Ali Int'l Airport is 17.7 miles, along with KY State Fair Grounds, and KY Kingdom and Hurricane Bay. Churchill Downs is 25 miles. Bernheim Forest (The Giants) is 7.6 miles. Jim Beam Distillery (The Kitchen Table) is 8 miles. Bardstown KY is 27 miles. The Whistle Stop in Glendale KY is 32 miles. Locally we have Kart Kountry .8 miles and coming soon is out Aquatic Center and Asylum Paintball. Lots to do!

Guest favorite
The entryway features a well-maintained front garden with clusters of purple flowers surrounded by green foliage. A pathway leads to the front door, which is framed by light-colored brick and flanked by decorative shrubs. Window shutters can be seen in a complementary shade.
Home in Shepherdsville
4.89 out of 5 average rating, 97 reviews

3 BED/2 BA on Bourbon Trail - Pet Friendly

Perfectly located get away located on Kentucky’s famous Bourbon Trail! Relax with the whole family in this home away from home! Equipped with all your needs from cooking meals to enjoying coffee on the back deck, this home has you covered! Centrally located close to I-65 right outside of Louisville and Bardstown. Enjoy the neighborhood park and lake for evening walks or fishing! Nearby you’ll find grocery stores, local food and coffee and the best of the city and the country all in one place!

Top guest favorite
A welcoming entrance features a large covered porch supported by wooden beams. Two black and white chairs are positioned to the sides of the front door, with a small side table nearby. The lush landscaping includes neatly trimmed shrubs and a brick pathway.
Home in Shepherdsville
5.0 out of 5 average rating, 29 reviews

Cozy Home Near the Bourbon Trail & KY Derby

Welcome to our spacious 4-bedroom home, located between Kentucky’s iconic Bourbon Trail and all that Louisville has to offer. Just a few minutes drive to I65 close to E-town, Bardstown or Louisville. Nestled in a small, quiet neighborhood, comfortable and convenient for families, friends, or groups looking to explore the heart of Kentucky. Whether you’re here for bourbon, events, the Kentucky Derby, or relaxation, this home is your perfect getaway. Book now to make unforgettable memories!

Guest favorite
The cabin features a rustic wooden exterior with a green metal roof, framed by surrounding trees. A welcoming front porch with railings and lights enhances the entrance. Two garage doors are visible on the lower level, creating an inviting atmosphere as dusk approaches.
Cabin in Shepherdsville
4.91 out of 5 average rating, 58 reviews

Pickleball*Hot Tub*Pool*Bourbon Trail*Sleeps 16!

Welcome to the Cabin at Rams Run! This newly renovated 5-bed, 5 full-bath cozy cabin is the perfect resort for adult trips and families alike. Situated on top of a ridge just above the James B. Beam Distillery, the cabin is in a perfect location directly between the culture and attractions of Louisville, and the distilleries of Bardstown--the bourbon capital of the world! After touring the Kentucky countryside, enjoy the hot tub, game room with pool table, or the indoor pickleball court!

Superhost
The exterior of a two-story home is shown, featuring a classic design with beige siding and brown shutters. A welcoming front door is framed by two windows, while a paved driveway leads to the garage. A basketball hoop stands in the yard, surrounded by a green lawn.
Home in Shepherdsville
4.75 out of 5 average rating, 68 reviews

Shepherdsville Cozy Home with Lakeside views

**Welcome to Your Cozy Kentucky Retreat!** Escape to tranquility in this charming, fully furnished home nestled right on the lake. Perfectly suited for both a peaceful weekend getaway or an extended stay, this property offers all the comforts of home with a touch of Southern hospitality. Book now to experience the ideal Kentucky retreat and make lasting memories! We have 4 bedrooms in our home, all are upstairs. We look forward to hosting you and ensuring you have a wonderful stay!

Superhost
Home in Lebanon Junction
5.0 out of 5 average rating, 3 reviews

Bourbon Trail Retreat | 21 Acres Near Louisville

NEW LISTING! Experience Kentucky and the Bourbon Trail at this private 21-acre retreat—just 30 minutes from Downtown Louisville! Sleeps 12 with 3 bedrooms + a bonus sleeping area with attached full bathroom. Enjoy a private fishing pond (KY fishing license required), fire pit, spacious deck for dining and relaxing, & exploring. Bordering 1,000 acres of Camp Crooked Creek with easy access to the Bourbon Trail, Bernheim Forest, Elizabethtown, Bardstown, and Louisville attractions.

Top guest favorite
The outdoor space features a concrete patio surrounded by colorful trees, showcasing a blend of autumn hues. A charcoal and gas grill is covered, positioned on one side of the patio. The entrance door to the lower-level unit is visible, offering a private and secure access point.
Guest suite in Shepherdsville
4.99 out of 5 average rating, 101 reviews

Private 1000 sq ft 1-bedroom lower level apartment

Relax in this beautiful wooded setting in Bourbon Country less than 4 miles from I-65. Private entrance into freshly painted 1-bedroom unit with new kitchen and 9' ceilings. Perfectly located near 19 Bourbon Distilleries, 4 Wineries, Bernheim Forest, Knob Creek Gun Range, Churchill Downs and other exciting destinations. Jim Beam Distillery & Forest Edge Winery are 7 min away. There is a seasonal (shared) concrete patio, deck and pool available in the warmer months.

Top guest favorite
Dome in Mount Washington
4.98 out of 5 average rating, 258 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.

Superhost
A comfortable living area is presented with a spacious grey sofa and an armchair positioned on a patterned rug. Natural light streams through the framed windows, and a stone fireplace serves as a focal point, complemented by a wall-mounted television.
Home in Louisville
4.87 out of 5 average rating, 141 reviews

Cute, Cozy, & Clean Home in Louisville

Welcome to this gem that is 20 minutes from Churchill Downs and Downtown Louisville. 15 minutes from the airport and Jim Beam! With parking galore, plenty of bedrooms, and a huge backyard, this is the ideal space for family and friends to reunite and connect. This is the perfect spot to stay to explore Louisville and surrounding areas - close enough to the excitement but far enough away to rest and relax! We would be happy to host you!

Top guest favorite
Home in Radcliff
4.96 out of 5 average rating, 28 reviews

Rockstar~Indoor pool~Sleeps 10~Gameroom~Volleyball

Rockstar is a bold rock ’n’ roll retreat built for unforgettable stays. This 4 bedroom, 3.5 bath home sleeps 10 with 5 beds, including two king primary suites. Make a splash in the private indoor pool, battle it out in the game room with ping pong, foosball and giant Connect 4, then fire up the grill on the large deck with picnic tables. The yard features volleyball and cornhole. Turn it up, kick back, and live like a Rockstar!

Popular amenities for Shepherdsville vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Shepherdsville's top sights

Bernheim Arboretum and Research Forest

225 locals recommend

James B Beam Distilling

179 locals recommend

Kart Kountry

26 locals recommend

Other great vacation rentals in Shepherdsville

Top guest favorite
Home in Elizabethtown
5.0 out of 5 average rating, 58 reviews

Elizabethtown Sports Park/Bourbon Trail

Top guest favorite
A modern two-story home showcases a clean, white exterior with contrasting gray siding accents. The spacious front driveway leads to a large garage. The well-maintained lawn features a small tree and is flanked by a few neighboring homes in the background.
Home in Mount Washington
5.0 out of 5 average rating, 15 reviews

Whiskey, Horses, & Hospitals

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, 36 reviews

Bourbon Trail Cabin

Superhost
Apartment in Shepherdsville
4.78 out of 5 average rating, 9 reviews

Flip Flops & Fireflies: Back2Basic

Top guest favorite
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.
Cabin in Lebanon Junction
4.98 out of 5 average rating, 43 reviews

Woodland Oasis: Historic Cabin with Modern Comfort

Top guest favorite
Home in Coxs Creek
5.0 out of 5 average rating, 53 reviews

Distillery Overlook Barndo Home

Superhost
Apartment in Brooks
4.98 out of 5 average rating, 47 reviews

Cozy Studio in Brooks

Guest favorite
An exterior view of the cabin displays a spacious deck adorned with wooden chairs and tables, nestled among trees. Warm light fixtures create a welcoming ambiance. The lower level features a hot tub, partially visible among the greenery, enhancing the natural setting.
Cabin in Shepherdsville
4.89 out of 5 average rating, 63 reviews

Moonlight Ridge Cabin Retreat

When is the best time to visit Shepherdsville?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$20,917 GYDG$23,008 GYDG$21,544 GYDG$27,401 GYDG$30,120 GYDG$22,381 GYDG$23,218 GYDG$21,753 GYDG$30,329 GYDG$22,381 GYDG$20,498 GYDG$20,917 GYD
Avg. temp2°C4°C9°C15°C20°C25°C27°C26°C22°C16°C9°C4°C

Frequently Asked Questions

  • What are the best places to stay in Shepherdsville?

    Many visitors choose to stay in Shepherdsville’s residential neighborhoods or near riverfront parks for easy access to local attractions. Rentals in quiet areas are often preferred for a more relaxed experience.

  • What are the best things to do in Shepherdsville with kids?

    Kids can enjoy playgrounds in community parks, interactive activities at museums, and family-friendly bowling or mini-golf. Animal encounters and seasonal festivals provide more options around Shepherdsville.

  • What are some of the best things to do in Shepherdsville?

    Shepherdsville has historic sites, nature parks, and local distilleries to explore. Many visitors enjoy browsing antique shops, sampling bourbon at nearby distilleries, or walking riverfront trails.

  • How is the weather in Shepherdsville?

    Shepherdsville has cool winters with highs near 44°F (6°C) and warm summers reaching around 89°F (32°C). Spring and fall bring mild temperatures and occasional rainfall, so layered clothing is often recommended.

  • When is the best time to visit Shepherdsville?

    Late spring through early fall is frequently suggested, as temperatures are milder and local festivals highlight the area’s food and culture. Blooming landscapes and outdoor activities are popular during these months.

  • What are the best places to visit in Shepherdsville?

    Popular spots in Shepherdsville include local distilleries, riverside parks, and antique shops. Those interested in area history can explore museums or historic landmarks around the city.

  • What are some hiking trails in Shepherdsville?

    Shepherdsville has green spaces with forested walking and hiking trails, many around area parks. Explore woodland paths and riverside trails, or venture just outside the city for nature preserves.

  • What are some family activities we can do in Shepherdsville?

    Families can explore public parks, visit interactive museums, and enjoy mini-golf or bowling. Seasonal events and local fairs add opportunities for shared experiences around Shepherdsville.

  • What are some of the best day trip ideas from Shepherdsville?

    Day trips from Shepherdsville often include exploring historic Louisville, venturing to area distilleries on the Kentucky Bourbon Trail, or hiking in state parks just outside the city. Cultural centers and riverfront attractions are frequently suggested nearby.

  • Are there any pet friendly accommodations available in Shepherdsville?

    Shepherdsville has pet-friendly accommodations, especially in houses and apartments near parks or walking trails. Many rentals welcome travelers with pets, providing space for walks and outdoor activities.

  • What are some local tips for visiting Shepherdsville?

    Locals suggest stopping at small distilleries, exploring antique markets, and hiking riverside trails. Wearing comfortable shoes, reserving tastings in advance, and checking seasonal calendars can help make the most of your visit.

  • What is Shepherdsville known for?

    Shepherdsville is known for its Bourbon Trail connections, locally rooted distilleries, and riverfront areas. The city has a history of agriculture and craft traditions, reflected in local events and attractions.

  • What are the best hidden gems to explore in Shepherdsville?

    Shepherdsville has antique shops with unique finds, small craft distilleries, and nature trails in lesser-known parks. Visitors sometimes discover historic sites or locally owned restaurants that reflect the area’s traditions.

  • What are the best foods to try in Shepherdsville?

    Shepherdsville has Southern-inspired dishes frequently suggested, like fried chicken, barbecue, and country ham. Locally baked pies and homestyle sides are also popular in area restaurants.

  • What should I bring for a trip to Shepherdsville?

    Pack comfortable clothing suitable for walking and outdoor activities, along with layers for variable temperatures between 28–89°F (-2–32°C). A rain jacket or umbrella is useful in spring and fall, and sunscreen for summer visits.

  • What is the nightlife in Shepherdsville like?

    Nightlife in Shepherdsville centers around neighborhood restaurants, casual bars, and venues with live music on weekends. The atmosphere is laid-back, with local spots often hosting community events and performances.

  • What are the most popular events or festivals in Shepherdsville?

    Shepherdsville has seasonal festivals celebrating Kentucky tradition, including county fairs and bourbon-related events, often recommended in late summer and early fall. Community gatherings and holiday parades are also popular.

  • Are there family friendly vacation rentals in Shepherdsville?

    Shepherdsville has family-friendly vacation rentals in residential neighborhoods and near parks. Many homes and apartments include flexible layouts for groups or families travelling together.

Destinations to explore