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House holiday rentals in Shelbyville

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Popular amenities for Shelbyville house rentals

House rentals with a pool

Guest favourite
Home in Shelbyville
4.97 out of 5 average rating, 30 reviews

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

AngelaRating, 5 stars1 week 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 stars2 weeks 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, 108 reviews

Stay@Peppermint Cottage Norton Commons w/breakfast

CarlaRating, 5 stars3 days ago
Nicole was, without a doubt, the best host I’ve ever had. From the moment we arrived, we were greeted with thoughtful touches thoughtfully placed throughout the home—each one clearly personalized with our family in mind. It felt less like a rental and more like staying at a close friend’s house. The bed was incredibly comfortable, and the entire home was spotless. Nicole’s attention to detail and genuine hospitality made our stay truly special. I would wholeheartedly recommend this rental to anyone looking for a warm, welcoming, and memorable experience.
Top Guest favourite
Home in Bagdad
5 out of 5 average rating, 31 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 stars2 weeks 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!
Superhost
Home in Taylorsville
4.8 out of 5 average rating, 49 reviews

The Cozy Lake Place Cottage 75

LuisRating, 5 stars1 month ago
We love your house, thank you for everything
Superhost
Home in Lawrenceburg
4.81 out of 5 average rating, 166 reviews

Restful Bourbon Trail Lodge with Pool and Hot Tub

SuzanneRating, 5 stars3 days ago
Fantastic stay at this beautiful home. Hot tube and pool were clean and were very accessible. Kitchen and grill were also clean and easy to use. Every part felt very homey and comfortable. This is a great place to stay for all things Bourbon Trail because it’s very centrally located.

Weekly house rentals

Guest favourite
Home in Simpsonville
4.92 out of 5 average rating, 12 reviews

Eastern Sky

LindseyRating, 5 stars3 days ago
The home was beautiful, with very nice decor! Sectional and beds were comfortable! The dining area was beautiful. We stayed here as we went shopping at the outlet mall in Simpsonville. Everything was great, except for the air conditioning not working right our first night, but the host was responsive and got someone out to fix it the morning of our second day. Would stay here again!
Top Guest favourite
Home in Frankfort
5 out of 5 average rating, 48 reviews

The Crafty Bourbon Bungalow Apartment

ChristinaRating, 5 stars3 days ago
We had a great stay here! Perfect little place to stay for a weekend! Host goes above and beyond to make you feel at home!!! Definitely recommend!!
Top Guest favourite
Home in Shelbyville
5 out of 5 average rating, 28 reviews

Bourbon by the Lake

JesseRating, 5 stars1 day ago
The house was perfect, the beds were soft and the host was very responsive. We would absolutely stay again, and our kids enjoyed the kayaking, fishing, and fireflies. The location was close to many distilleries and food options while also allowing a private peaceful experience. We were very pleased with our stay. The dock on the water was a big plus!
Top Guest favourite
Home in Versailles
5 out of 5 average rating, 7 reviews

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

JamesRating, 5 stars6 days ago
Place was amazing! John was responsive and recommended some local restaurants that were great! Close to distilleries. Beautiful country. The hot tub controls are on the back "under the cover once you open it". Maybe the bourbon didn't help us lol. Golf simulator was a blast! We actually cut our evening short to go back to the place and hang out! Don't miss this special gem!
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 stars2 months 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.
Top Guest favourite
Home in Shelbyville
5 out of 5 average rating, 11 reviews

Luxurious Kentucky Bourbon Trail Getaway by Lville

TinaRating, 5 stars8 months ago
It’s beautifully decorated, very clean and well equipped. We fully enjoyed our stay and would stay here again. It was an easy walk to downtown to visit local shops and eateries.

Private house rentals

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 stars4 days ago
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!
Top Guest favourite
Home in Midway
5 out of 5 average rating, 37 reviews

Bourbon Trail ~ Pickleball ~ Hot Tub ~ Mini-Golf

AbbeyRating, 5 stars4 days ago
This is our second time here. Even better this time! We’ve been in the winter and now in the summer. I brought the kids down and they have so much fun. We went horse back riding and drove down to red river gorge for a day too. Lots to do and beautiful.
Guest favourite
Home in Taylorsville
4.92 out of 5 average rating, 25 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!
Guest favourite
Home in Louisville
5 out of 5 average rating, 53 reviews

Countryside Getaway

ZacharyRating, 5 stars6 months ago
We stay here every year when visiting family for thanksgiving. It is perfect for our small family. The host is always so responsive. The property is beautiful. I can’t recommend this airbnb highly enough. Thank you Gordana!!
Top Guest favourite
Home in Frankfort
4.99 out of 5 average rating, 74 reviews

Backyard Bourbon Retreat

KellyRating, 5 stars1 week ago
The house was spotless and beautifully decorated with Kentucky charm and had everything we needed for our stay. The beds are incredibly comfortable and the shower water pressure is fabulous! From the point of booking Bobbie was incredibly responsive. We loved the thoughtful touches like the little bottles of bourbon, which really made us feel very welcome to the area! We HIGHLY recommend Bobbie's place for your next vacation stay!
Top Guest favourite
Home in Frankfort
4.98 out of 5 average rating, 62 reviews

MacAttie Acres

TriciaRating, 5 stars1 week 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 Frankfort
5 out of 5 average rating, 56 reviews

Bourbon Central - 1.8 miles to Buffalo Trace

MichaelRating, 5 stars1 week ago
This home is amazing! Brian goes to great lengths to make everything about staying here a 5 star experience. The home is luxurious and has many thoughtful details. Even though the home is right in downtown Frankfort, it is peaceful and serene once inside. My wife and I loved sitting on the back patio nestled right next to the Kentucky River. It is just a short walk to many restaurants, bakeries, and coffee shops. If I go back to Frankfort, this is the place I want to stay.
Top Guest favourite
Home in Frankfort
4.97 out of 5 average rating, 30 reviews

Green Acres

MariaRating, 5 stars1 week ago
We enjoyed our stay. Nice to be out of town a bit but not too far from many, many things to do

Quick stats about house rentals in Shelbyville

  • Total rentals

    20 properties

  • Nightly prices starting at

    $116 NZD 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

  • Wi-Fi availability

    20 properties include access to Wi-Fi

Destinations to explore

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