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.
Superhost
Home in Shelbyville
4.76 out of 5 average rating, 59 reviews

Pool*HOT TUB*Bourbon Trail

NicholasRating, 5 stars2 weeks ago
Toni was great and the place was exactly as advertised.
Top Guest favourite
Home in Lexington
4.97 out of 5 average rating, 116 reviews

Summer Bliss! Pool&FunZone Oasis! Hottub! GameRm!

NicoleRating, 5 stars4 days ago
This home was amazing. The pool was great and exactly as described. Harrison was a great host!!
Top Guest favourite
Home in Prospect
5 out of 5 average rating, 108 reviews

Stay@Peppermint Cottage Norton Commons w/breakfast

CarlaRating, 5 stars4 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 Lexington
5 out of 5 average rating, 103 reviews

Game room! 5 beds an 4 bedrooms

ShellyRating, 5 stars5 days ago
We stayed at The Nest for 5 nights and enjoyed every minute of it. It has a very homey feel to it. Jeff has provided everything you need for a vacay and a few things you might have forgotten to bring. We had family over for a cookout while we were in town, we had like 12-14 people over for dinner and we had plenty of room for everyone. The kids loved the game room. The pool was amazing, it was extremely clean. Jeff even has pool floaties for his guests. He came over during our stay just to clean the pool. He takes great care of his property. The backyard is spacious and beautiful. The neighborhood is so pretty. We felt very safe. I would go out for a walk every day, it was quiet, beautiful and peaceful. This house is honestly close to everything, most of it within walking distance. Jeff is an amazing host. This is our go-to AirBnB from now on every time we come to Kentucky. Thank you Jeff for a great stay and for providing the foundation for some wonderful family memories.
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 stars1 month 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.

Weekly house rentals

Top Guest favourite
Home in Frankfort
5 out of 5 average rating, 48 reviews

The Crafty Bourbon Bungalow Apartment

ChristinaRating, 5 stars4 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 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 Shelbyville
5 out of 5 average rating, 37 reviews

Historic Downtown~Heart of Bourbon Trail

RebeccaRating, 5 stars3 weeks ago
Stayed at the Washington Belle for my wedding weekend and it was perfect! Myself and my bridesmaids got ready there and there was plenty of space, light, and rooms to get ready in! Everywhere is decorated so cute and the house is perfectly situated to the Shelbyville Conference Center and the downtown Main Street. We loved staying there and the host is so nice! Such a charming house!
Top Guest favourite
Home in Frankfort
5 out of 5 average rating, 88 reviews

*Long Pour: Your Luxury Downtown Bourbon Home*

AnnRating, 5 stars3 weeks ago
Long Pour was an amazing place to stay while in Frankfort. The decor was perfectly curated for the Bourbon Trail. Lauren provided everything we needed and more: Buffalo Trace coffee, tea, robes, face masks, just to name a few. The beds were comfortable with nice linens and towels. It was very walkable to restaurants and bars. Would highly recommend for a memorable stay.
Top Guest favourite
Home in Louisville
5 out of 5 average rating, 18 reviews

Historic 1905 Kentucky Farmhouse

LyndseyRating, 5 stars4 days ago
We stayed at The Farmhouse during a trip for a baseball tournament. We chose it for it's wheelchair accessibility and it did not disappoint! The ramp outside and the extra large doorways were a huge help for my Dad while he was maneuvering in & out of the home. The location was private, peaceful, and beautiful. The house was spacious, had comfortable beds and furniture, a fully stocked kitchen, and clean bathrooms. Our only note is that the upstairs bedroom was hot!!! We found a window air unit in a closet and put it in. It would have been nice if that had been done prior to our arrival. The hosts we're quick to answer questions we had and helped us anyway they could. Wonderful place to stay!
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.
Guest favourite
Home in Shelbyville
4.96 out of 5 average rating, 28 reviews

~Bourbon Trail~Hot Tub~Pool Table/Ping Pong~Derby~

WilliamRating, 5 stars2 months ago
We were a group of 4 couples visiting local distilleries. This place was fantastic! Local to Bulleit, Whiskey Thief, and a short drive to all of the big names. Welcoming and comfortable for the 8 of us, with a pool table to keep the guys occupied while the girls hit up the hot tub or chatted on the ridiculously comfortable sectional. Can’t think of a thing I would have asked for, this met all of our expectations.
Guest favourite
Home in Lawrenceburg
4.93 out of 5 average rating, 30 reviews

Lakefront. Boat Dock. Private Bar. Hot Tub

JordanRating, 5 stars2 days ago
Great location and beautiful home. Definitely a go to place to stay for spending time at beaver lake.

Private house rentals

Top Guest favourite
Home in Midway
5 out of 5 average rating, 37 reviews

Bourbon Trail ~ Pickleball ~ Hot Tub ~ Mini-Golf

AbbeyRating, 5 stars5 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.
Superhost
Home in Shelbyville
4.72 out of 5 average rating, 18 reviews

Peace and Quiet Close to Louisville - 80+ Acres

ManuelRating, 5 stars2 weeks 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.
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!!
Guest favourite
Home in Lawrenceburg
4.95 out of 5 average rating, 62 reviews

Bourbon Crossing II

TimothyRating, 5 stars1 day ago
We absolutely loved our stay at this bourbon-themed Airbnb in Lawrenceburg! From the moment we walked in, we could tell this place was something special. The attention to detail is incredible — from the tasteful bourbon-inspired décor to the high-quality furnishings and thoughtful amenities. Every inch of the space felt curated, cozy, and inviting. The bed was exceptionally comfortable (we slept better than at home!), and the whole place was spotless and beautifully maintained. The full kitchen had everything we needed. Location-wise, it was perfect. Just a short drive from Buffalo Trace, this gem is ideally situated between Louisville and Lexington along the Bourbon Trail. It was the perfect home base for our adventures, and it was great to return to such a peaceful and relaxing space after a full day of exploring. If you’re looking for a place that’s clean, stylish, comfortable, and perfectly located for exploring Kentucky bourbon country, look no further. We’ll definitely be back!
Top Guest favourite
Home in Louisville
5 out of 5 average rating, 47 reviews

Convenient & Cozy! Close 2 it all in Louisville!

AllisonRating, 5 stars2 weeks ago
Home was exactly as described— very clean, clear instructions for check in and check out. Nice quiet neighborhood close to downtown and all the distilleries and restaurants. Would definitely stay here again.
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 stars1 week 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 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.

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