House vacation rentals in Shepherdsville

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Popular amenities for Shepherdsville house rentals

House rentals with a pool

Top guest favorite
Home in Mount Washington
5 out of 5 average rating, 36 reviews

Pool*Pickleball Bldg*HotTub*Speakeasy*BourbonTrail

StacieRating, 5 stars1 week ago
This place absolutely exceeded our expectations. The home was spacious, clean, and loaded with more amenities than we anticipated. The speakeasy was such a cool touch and gave the stay a unique vibe true to the reason we were visiting the area. We had a blast on the pickleball court, and the video games were a hit with everyone. Plenty of parking made things easy, especially since we were on motorcycles—very bike-friendly setup. Access was smooth, and the whole experience felt effortless from check-in to check-out. It is very obvious from the moment we booked until the last goodbye message that there was a great deal of thought put into this home and making it an experience for all to enjoy. Would absolutely stay here again. Highly recommend!
Superhost
Home in Bardstown
5 out of 5 average rating, 4 reviews

Farmhouse Luxury! 10 Min to Distilleries! Pool! Ho

LiamRating, 5 stars1 month ago
The home was perfect. Well maintained, very clean. Comfortable furnishings, everything you could ask for in the main house. The game-room / garage was the cherry on top!
Superhost
Home in Shelbyville
4.77 out of 5 average rating, 52 reviews

Pool*HOT TUB*Bourbon Trail

GiovanniRating, 5 stars1 month ago
Amazing place, would stay here again, thank you Tony!
Superhost
Home in New Albany
4.85 out of 5 average rating, 52 reviews

ꕥLuxꕥHeated* Pool/Hot Tub/Gamerooms/Firepit/

AbigailRating, 5 stars1 month ago
Great place! Lots of activities at the house. Clean & Tyler was very communicative!
Top guest favorite
Home in Prospect
5 out of 5 average rating, 100 reviews

Stay at Peppermint Cottage in Norton Commons!

KatarinaRating, 5 stars1 week ago
Highly recommend staying at The Peppermint Cottage! The location and house were great. Nicole was also very responsive and a great host. Will definitely be back!
Top guest favorite
Home in Bagdad
5 out of 5 average rating, 26 reviews

Private Estate on Bourbon Trail w/ Beautiful Pool

SeanRating, 5 stars1 week ago
Spent the weekend for a bachelor party, this property was amazing!! Super private, plenty of space and great amenities. Our host had such great recommendations for distilleries, places to eat, and golf. Just an amazing stay and an amazing home. If you are looking for a place to stay along the bourbon trail, do yourself a favor and book this one!!
Superhost
Home in Taylorsville
4.82 out of 5 average rating, 45 reviews

The Cozy Lake Place Cottage 75

CaraRating, 5 stars1 month ago
Great stay for a quick vacation.
Top guest favorite
Home in Lebanon
4.94 out of 5 average rating, 69 reviews

Ticky's Cottage at Empire Estate

KentRating, 5 stars6 months ago
As advertised! We were visiting a family member and it was a good place to do that. Much better than a motel room! Host was friendly and helpful. Nice large grassy and wooded area for walking. Back away from the street and quiet. Would definitely stay there again.

Weekly house rentals

Guest favorite
Home in Central Business District
4.83 out of 5 average rating, 211 reviews

615 E Washington, Nulu Bourbon Trail

KyleRating, 5 stars2 weeks ago
The place was lovely and wonderfully centrally located. They were incredibly responsive and gave amazing check in instructions. The home while beautiful did have an interesting layout with the bedrooms. We would absolutely stay here again.
Top guest favorite
Home in Elizabeth
4.98 out of 5 average rating, 129 reviews

Cabin on Lake Close to Louisville Ky

ElizabethRating, 5 stars6 days ago
We stayed here for an Easter getaway with some friends and our dog. Everything was really clean, the kitchen was really well stocked, it was really quiet, and the space was perfect for all of us. The screened in porch was amazing…I wanted it to come home with me! Overall, great stay. Definitely recommend and would stay again!!
Superhost
Home in Butchertown
4.93 out of 5 average rating, 296 reviews

Guesthouse on Story- Bourbon Trail

CarolynRating, 5 stars1 month ago
This was our second stay at Guest House on Story, and was definitely as good, if not better than the first. Kim is an excellent and responsive host who strives to make sure your stay is exactly what you need. We had a large group of adults visiting Louisville to celebrate a birthday weekend, and we had plenty of space to spread out and relax. The area has fun walkable bars, breweries, and cocktail lounges, along with restaurants! Highly recommend Tartan House and Biscuit Belly. Guests should be aware as others have mentioned that given the location in Butchertown, there is occasionally a notable smell outside. It very much depends on the direction of the wind and day/time of the week. Do know though that you cannot smell this inside the house! We caught a whiff outside here and there, but definitely not the entire time. Highly recommend Guest House on Story, and I'm sure we will stay again when in Louisville with a large group.
Guest favorite
Home in Louisville
4.95 out of 5 average rating, 244 reviews

Highlands Haven Cottage

MartaRating, 5 stars2 weeks ago
This is my second stay at Dianas place, working on booming my third one. Vibrant and safe neighborhood, full of various restaurants, coffee shops, bars and funky boutiques. Very walkable. The space has luxurious shower, linens and a gas stove, home away from home. Friendly, and accessible host.
Guest favorite
Home in Old Louisville
4.93 out of 5 average rating, 187 reviews

Beautiful space with a garage.

LyndsayRating, 5 stars3 weeks ago
The property was exactly as listed and perfect for what we needed. We felt safe with the external cameras and other safety features. The bed was super comfortable and the space was very clean and well organized. The binder provided was clear and the included "In case of Emergency" plan was an appreciated add in, that we were glad wasn't needed but comforting to have. Added bonus for the garage space provided. Couldn't ask for better. Would 100% stay again.
Guest favorite
Home in Louisville
4.96 out of 5 average rating, 262 reviews

Home near the Highways

TiffanyRating, 5 stars2 months ago
My family and I loved Ross place!!! His communication was quick and left very clear instructions. Upon arrival, he even left music on to welcome us. The home was exactly as pictured and was very peaceful. It accommodated our needs and highly recommend 👌.
Top guest favorite
Home in Bardstown
4.83 out of 5 average rating, 114 reviews

Upscale 1 Story Bourbon Trail XLBeds King 2 Single

DianeRating, 5 stars5 months ago
The house was really nice, great location. The only thing I had trouble with was the lock box.
Guest favorite
Home in Elizabethtown
4.85 out of 5 average rating, 133 reviews

The Nantucket Suites

NicoleRating, 5 stars1 week ago
absolutely love the place it was just as described big enough for everybody and only suggestion was would be for a guest sign in book and a guest binder for the rules of the home. we loved the place and felt rigth at home. we left little trinkets and the house for the next guest to find.

Private house rentals

Superhost
Home in Jeffersonville
4.89 out of 5 average rating, 9 reviews

Cozy 3-Bedroom Home in Jeffersonville, IN

AaliyahRating, 5 stars6 months ago
Quite Great location at peacful clean home and Host was Awesome and responsive and helpful with all question and would love to stay again !!!
Top guest favorite
Home in Louisville
4.97 out of 5 average rating, 60 reviews

Quiet Area | Expressway Nearby | Families Welcome

Melissa-MayelaRating, 5 stars2 weeks ago
Our stay at Lynn’s place was enjoyable from beginning to end. Extremely pleased with the entire experience. I will definitely return to her home for future accommodations while visiting the Louisville area.
Top guest favorite
Home in Campbellsville
5 out of 5 average rating, 9 reviews

Three Bedroom Country Cottage

RebeccaRating, 5 stars2 months ago
We absolutely loved this charming farmhouse and farm. The longhorns were close by and actually walked toward us as we stood looking at their majestic beauty. The walking trail led us past the pond and down to the rapid creek. We were able to pet the horse and donkey too. The house is very clean and comfortable plus adorable. We felt like we were way out in the country yet we were very close to anything we might need. The bed was comfortable and the kitchen well stocked. The view from the back porch was beautiful. Being there gave us a “peaceful easy feeling”. We came to visit family and will definitely stay here again. Darlene is the perfect hostess.
Guest favorite
Home in Louisville
4.92 out of 5 average rating, 104 reviews

Bourbon House 1 | Expo Center - Private Backyard

AngelaRating, 5 stars3 weeks ago
Very pleased with our stay. Host was responsive and accommodating. Lots of room and great location; hope to stay again!
Top guest favorite
Home in Lebanon
4.92 out of 5 average rating, 98 reviews

The BourbonTrail Getaway

JoshuaRating, 5 stars3 weeks ago
I have stayed here more than once. This is the best spot in the area. It's close to everything you need and feels like home. Peggy is extremely helpful and the place is very comfortable
Top guest favorite
Home in Louisville
4.99 out of 5 average rating, 149 reviews

Newly Renovated Derby House

MistyRating, 5 stars1 week ago
Jason’s place was just as described, immaculately clean, and homey. The neighborhood was quiet and felt safe. Beds were comfortable.
Top guest favorite
Home in Pleasureville
5 out of 5 average rating, 96 reviews

Pleasureville - The name says it ALL

CynthiaRating, 5 stars1 week ago
The home met our needs perfectly! Lorrie was very responsive to every communication -- and provided helpful recommendations on local gems for dining and shopping. Wish we could have stayed longer just to soak up the scenery and fresh air while sitting on the covered patio.
Guest favorite
Home in Old Louisville
5 out of 5 average rating, 8 reviews

NEW! Award Winning Luxury 4 BR - Prime Louisville!

MikeRating, 5 stars2 weeks ago
Great place and very responsive host. Would stay here again. Charming area and the home offered plenty of space.

Quick stats about house rentals in Shepherdsville

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ294 before taxes and fees

  • Total number of reviews

    910 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore