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Holiday houses in Shepherdsville

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Quick stats about holiday rentals in Shepherdsville

  • Total holiday rentals

    Explore 30 holiday rentals in Shepherdsville

  • Nightly prices starting at

    Shepherdsville holiday rentals start at $112 AUD per night before taxes and fees

  • Verified guest reviews

    Over 2,280 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Shepherdsville holiday 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 holiday rentals in Shepherdsville

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

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Top Guest favourite
Cabin in Shepherdsville

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! 🥃✨

ValueFamilyPets

4.98 out of 5 average rating, 122 reviews
Guest favourite
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

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!

ValueLocationLaundry

4.99 out of 5 average rating, 104 reviews
Guest favourite
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

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!

LocationFamilyQuiet

4.86 out of 5 average rating, 36 reviews
Top Guest favourite
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

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!

FamilyLocationBathroom

5.0 out of 5 average rating, 29 reviews
Guest favourite
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

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!

LocationFamilyCondition

4.92 out of 5 average rating, 59 reviews
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

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!

LocationValueView

4.75 out of 5 average rating, 69 reviews
Top Guest favourite
Home in Elizabethtown

Elizabethtown Sports Park/Bourbon Trail

Escape to our spacious retreat just minutes from Elizabethtown Sports Park and 20 minutes from world-class Bourbon Trail distilleries. Nestled in the woods, it offers privacy and room for the whole family. After games or tastings, relax in the hot tub, gather around the firepit, and soak in the peaceful setting. The perfect base for tournaments, bourbon adventures, or simply unwinding in the Bluegrass. Whether it's competition or relaxation that brings you here this home has it all!

FamilyLocationLayout

5.0 out of 5 average rating, 59 reviews
Guest favourite
Home in Shepherdsville

3 BED/2 BA on Bourbon Trail - Pet Friendly

Perfectly located get away 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, coffee and the best of the city and the country all in one place!

FamilyLocationHeating

4.89 out of 5 average rating, 97 reviews
Superhost
Home in Lebanon Junction

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.

FamilyIndoor spacesCleanliness

5.0 out of 5 average rating, 3 reviews
Top Guest favourite
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

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.

ValueLocationDecor

4.99 out of 5 average rating, 101 reviews
Top Guest favourite
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

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

ValueLocationComfort

4.89 out of 5 average rating, 347 reviews
Top Guest favourite
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

Whiskey, Horses, & Hospitals

New Construction! Located less than 30 minutes from the heart of Louisville! And Under 25 minutes from the airport. Shopping, interstates, hospitals & parks are all within 25 minutes. 3 bedrooms, 1 loft, and 2 full bathrooms upstairs, and 1/2 bath on main floor! Washer + dryer on site! Private office + additional study area located upstairs in bedroom 3. Complimentary overnight Level 2 EV charging is available for one vehicle per reservation.

FamilyLocationCleanliness

5.0 out of 5 average rating, 16 reviews

Popular amenities for Shepherdsville holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Shepherdsville's top sights

Bernheim Arboretum and Research Forest

226 locals recommend

James B Beam Distilling

179 locals recommend

Kart Kountry

27 locals recommend

Other great holiday rentals in Shepherdsville

Top Guest favourite
Home in Radcliff

Rockstar~Indoor pool~Sleeps 10~Gameroom~Volleyball

LocationFamilyHiking

4.96 out of 5 average rating, 28 reviews
Top Guest favourite
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

Woodland Oasis: Historic Cabin with Modern Comfort

ValueFamilyOutdoor spaces

4.98 out of 5 average rating, 43 reviews
Superhost
Apartment in Shepherdsville

Flip Flops & Fireflies: Back2Basic

FamilyCleanlinessAccuracy

4.78 out of 5 average rating, 9 reviews
Top Guest favourite
Home in Coxs Creek

Distillery Overlook Barndo Home

FamilyLocationHospitality

5.0 out of 5 average rating, 53 reviews
Top Guest favourite
Apartment in Brooks

Cozy Studio in Brooks

FamilyValueKitchen

4.98 out of 5 average rating, 47 reviews
Guest favourite
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

Moonlight Ridge Cabin Retreat

ValueFamilySleep quality

4.89 out of 5 average rating, 64 reviews
Guest favourite
A modern kitchen features white cabinetry, stainless steel appliances, and a large island with a blue-lit countertop. The space is brightened by natural light from a window, which overlooks a serene outdoor view.
Home in Vine Grove

The Grove!

ValueLocationTV

4.91 out of 5 average rating, 82 reviews
Guest favourite
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

Bourbon Trail Cabin

ValueFamilyCleanliness

4.94 out of 5 average rating, 36 reviews

When is the best time to visit Shepherdsville?

MonthJanFebMarAprMayJuneJulyAugSeptOctNovDec
Avg. price$139 AUD$153 AUD$144 AUD$183 AUD$201 AUD$149 AUD$155 AUD$145 AUD$202 AUD$149 AUD$137 AUD$139 AUD
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