House holiday rentals in Shelbyville

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Popular amenities for house rentals in Shelbyville

House rentals with a pool

Guest favourite
Home in Shelbyville
4.97 out of 5 average rating, 29 reviews

Pool is Open! + Hot Tub, 10 min to Bulleit

AngelaRating, 5 stars6 days ago
We had a wonderful stay. The family loved to pool and hot tub. We were close to many activities. Jill did an excellent job communicating with me and answering all my questions. We are looking forward to booking our next stay.
Guest favourite
Home in Shelbyville
4.94 out of 5 average rating, 70 reviews

B on the Bourbon Trail with pub, pool and hot tub

DanRating, 5 stars1 week ago
Had a excellent time at this location. The house was beautiful with great amenities including an amazing bar! Great location for visiting distilleries or Churchill Downs.
Top guest favourite
Home in Louisville
4.97 out of 5 average rating, 248 reviews

NEW Hot Tub, Expo, King Beds, Downtown, Churchill

BrianRating, 5 stars1 month ago
This house is absolutely fantastic. Super clean, super comfortable. The beds and pillows are amazing. I would highly recommend this house for any gathering. We were a group of four men doing bourbon trail related things, and relaxing at night next to the fire pit and in the hot tub.
Top guest favourite
Home in Prospect
5 out of 5 average rating, 107 reviews

Stay@Peppermint Cottage Norton Commons w/breakfast

BetsieRating, 5 stars2 weeks ago
Amazing stay. Nicole was super responsive and over the top helpful with info and recommendations. The house was beautiful. Everything exceeded our expectations. Looking forward to coming back !
Top guest favourite
Home in Bagdad
5 out of 5 average rating, 30 reviews

Private Estate on Bourbon Trail w/ Beautiful Pool

MeredithRating, 5 stars1 week ago
We had four adults and three kids staying at David’s place and it was great! It’s even better than the pictures. We loved the beautiful rural setting, yet also appreciated it was only 10 min from grocery stores and shopping. The pool and in home movie theater were big hits with our family. We grilled often and cooked in the kitchen, which had everything we needed. We appreciated all the space to spread out as well as the numerous areas to gather and play. We’d definitely stay here again!
Top guest favourite
Home in Lexington
5 out of 5 average rating, 102 reviews

Game room! 5 beds an 4 bedrooms

StephanieRating, 5 stars1 week ago
This place was very nice and Jeff was a terrific host! Perfect for a nice family getaway. Close to everything. If you are looking for fun and relaxation, this is the house. Game room was a huge bonus with 2 arcade games and several board games. The backyard is so cute, private and cozy. Kitchen was stocked with coffee and everything you need and the beds were comfy. This is a must stay. Very cute house! Loved it!
Guest favourite
Home in Taylorsville
4.93 out of 5 average rating, 104 reviews

Ridge Retreat 42 Sleeps 8 + Crib. NEW HOT TUB

GretchenRating, 5 stars3 weeks ago
Suzanne was accommodating, friendly and has a beautiful home. We were lucky to have spent our wedding weekend with her place. Thanks for making it easy.
Superhost
Home in Lawrenceburg
4.81 out of 5 average rating, 165 reviews

Restful Bourbon Trail Lodge with Pool and Hot Tub

JoshRating, 5 stars7 months ago
Overall great stay ! Exactly as described from the hot tub down to the amenities in the house. Very peaceful area and very easy to get to many area attractions! Thank you Joe !

Weekly house rentals

Guest favourite
Home in Simpsonville
4.91 out of 5 average rating, 11 reviews

Eastern Sky

ChloeRating, 5 stars2 weeks ago
We were in town for the Kentucky Ren Faire and it was a great location! Beautiful and peaceful location.
Top guest favourite
Home in Shelbyville
5 out of 5 average rating, 27 reviews

Bourbon by the Lake

DarrellRating, 5 stars1 month ago
The location is superb is you are trying to see Kentucky. The distance to Louisville, Lexington and Frankfort are all about equal. Shelbyville is a few miles away and it has some great restaurants and nice shopping. While staying there we visited Churchill Downs, Buffalo Trace and Shelbyville. The house has kayaks and a little fishing equipment. We spend a lot of time on the decks and fishing on the dock. This was a great, peaceful getaway from life at home.
Top guest favourite
Home in Shelbyville
4.97 out of 5 average rating, 33 reviews

oasis 522

DaveRating, 5 stars5 days ago
An absolute gem of a place right in the heart of Shelbyville. Lovely walk around town and a great Mexican restaurant right at your back door. An absolute highlight was the large vinyl collection and sound system that allowed you to play on the upstairs or downstairs speakers - amazing! Lewis also left a guitar which we enjoyed having a jam on while we stayed. The places looked even better in person than the photos and was very spacious. A wonderful stay in a beautiful small town with a lot of character
Superhost
Home in Versailles
5 out of 5 average rating, 5 reviews

Luxe Bourbon Trl~Game Rm~Golf Sim~Hot Tub~Fire Pit

VirginiaRating, 5 stars4 days ago
The house was gorgeous and had more than enough room for the nine of us. One of the most comfortable/clean places we have stayed and have no complaints!
Guest favourite
Home in Shelbyville
4.93 out of 5 average rating, 14 reviews

Shelbyville, KY - Bourbon Trail and Horse Country.

KerstinRating, 5 stars2 weeks ago
We enjoyed the spacious home with plenty of indoor and outdoor space to relax. The linens, bathrooms, and kitchen were very clean. We appreciated that the home is pet friendly and it was easy to walk our small dogs around the neighborhood. Angus was very responsive to our booking and request. We would stay here again and conveniently located near Shelbyville Country Club.
Top guest favourite
Home in Bagdad
5 out of 5 average rating, 87 reviews

LUX | HotTub | Firepit | Man Cave | On BRBN Trail!

AmyRating, 5 stars1 week ago
The house looks exactly like the photos. We hung out in the garage every night and had a blast. There was plenty of room for our group of 10 in there and plenty of activities to entertain us all. There are TVs in 3 of the bedrooms and 3 community spaces, so people also have the option of doing their own thing if they prefer. The bedrooms are spacious with huge closets. I like being able to unpack and put all my luggage away when I travel, so this was amazing. We had everything we needed in the kitchen, which was also nice. The house is located just down the road from Bulleit Distillery and about 25 minutes from Buffalo Trace, which is our favorite distillery, so that worked out great. From there, we could get to any distillery we were interested in visiting in about 45 minutes or less. The host of the property was fantastic to work with and was very responsive. I really appreciated their attention to detail and customer service. I highly recommend this home!
Top guest favourite
Home in Shelbyville
5 out of 5 average rating, 19 reviews

Bourbon Trail*4BR*Dog Friendly*6beds (3king)*Patio

ValentinRating, 5 stars3 weeks ago
Charlie and Kate were very helpful and responsive. Their place was clean and well furnished. Must stay at if you're looking for a place in Shelbyville!
Top guest favourite
Home in Pleasureville
5 out of 5 average rating, 98 reviews

Pleasureville - The name says it ALL

KalebRating, 5 stars1 month ago
Your place was absolutely amazing. The perfect old country home. The beds were super comfortable the kitchen has everything you need. The fire pit is an awesome perk to the property. I asked about going fishing and they were able to give me fantastic directions and we were able to catch some fish. I will definitely stay again when we come next year. Thank you so much for your hospitality and all your help during our trip.

Private house rentals

Top guest favourite
Home in Midway
5 out of 5 average rating, 35 reviews

Bourbon Trail ~ Pickleball ~ Hot Tub ~ Mini-Golf

DerekRating, 5 stars6 days ago
This house has been very well taken care of with nicely preserved midcentury details. My brothers and I really enjoyed our time there. Frankfurt is a relaxed city with amazing historical interest. We enjoyed golf, disc golf, and, of course, the local distilleries. The surrounding countryside is exactly what you would hope for in coming to Kentucky: ample rolling green hills and luxurious stables.
Top guest favourite
Home in La Grange
4.98 out of 5 average rating, 54 reviews

Where generations come to connect | Pool | Games

KimberlyRating, 5 starstoday
Everything we hoped for and more! There are so many places to hang out and relax both inside and out. We had the perfect mix of togetherness for our party of 9, and the ability to spread out and enjoy smaller groups or solitude. Great location outside Louisville, with plenty to do in the area and nearby grocery options. The kitchen was great and the master bath was luxurious. We loved that each bedroom had king beds! Deb was incredibly responsive, flexible and helpful. Our young adults loved the converted garage (which we dubbed the man cave due to its TV, fridge, pool table and foosball table). All the fun activities in the basement were great. We would definitely stay here again!
Guest favourite
Home in Taylorsville
4.92 out of 5 average rating, 24 reviews

Bourbon Trail Lake Home w/ Hot tub & King Bed

SteveRating, 5 stars1 week ago
The place was everything we wanted ton our stay. Sarah was fantastic in responding to any of our questions. I would definitely stay here again!
Superhost
Home in Shelbyville
4.72 out of 5 average rating, 18 reviews

Peace and Quiet Close to Louisville - 80+ Acres

ManuelRating, 5 stars1 week ago
Everything was perfect in this house! The best Airbnb option ever that we have rented in several countries. If you are looking for a place neer Shelbyville, Louisville, etc, this is the best option that you find.
Top guest favourite
Home in Frankfort
5 out of 5 average rating, 46 reviews

The Crafty Bourbon Bungalow Apartment

kerryRating, 5 stars6 days ago
Teri was wonderful! The house was super clean, had everything you need plus she provided extras like drinks and snacks. The house is very cozy, ideal for a couple. I would definitely stay here again.
Top guest favourite
Home in Frankfort
4.98 out of 5 average rating, 61 reviews

MacAttie Acres

TriciaRating, 5 stars4 days ago
Well, our group of 9 had an enjoyable time in this home! It was as advertised and extremely clean, comfortable and quiet. Cindy was just the sweetest and most respectful host always available to answer questions or give recommendations. Close to great distilleries and downtown Frankfort with cute shops and dining. The pool and hot tub were clean and working and the home was well stocked with basic necessities. Highly recommended and can't wait to come back!
Top guest favourite
Home in Jeffersonville
4.93 out of 5 average rating, 76 reviews

Beachfront River Cottage

TylerRating, 5 stars3 months ago
This was one of my favorite Air BNB stays to date. The cottage was so incredibly beautiful. It was super well stocked, clean, and there was a great amount of information about the property. We will definitely be back.
Guest favourite
Home in Lawrenceburg
5 out of 5 average rating, 28 reviews

Bourbon Trail! Tavern*Hot Tub * EV Charger

AmandaRating, 5 stars5 days ago
We enjoyed our stay at the Tavern. The house was very clean and the beds are comfortable. The kitchen was well stocked and had everything we needed. We enjoyed using the fire pit and hot tub after grilling steaks. The location was excellent for the bourbon trail. We were so close to everything we wanted to do.

Quick stats about house rentals in Shelbyville

  • Total rentals

    20 properties

  • Nightly prices starting at

    $90 SGD before taxes and fees

  • Total number of reviews

    780 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

Destinations to explore

  1. Airbnb
  2. United States
  3. Kentucky
  4. Shelby County
  5. Shelbyville
  6. House rentals