Cottage holiday rentals in Jefferson County

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Popular amenities for Jefferson County cottage rentals

Cottage rentals with a hot tub

Guest favourite
Cottage in Taylorsville
4.79 out of 5 average rating, 133 reviews

Anchor Rental

AlexRating, 5 stars1 month ago
Went to the Kentucky Derby with a group of friends. He graciously left us a derby care package at check-in. This place was perfect for 8 guys who just were looking for a place to sleep and have a BBQ in the driveway. Pillows could use an upgrade, and the closet in the bunk bed room had games and toys thrown about, but overall a good place to stay and worth the money of the rental.
Guest favourite
Cottage in Shelbyville
4.95 out of 5 average rating, 65 reviews

2025 KY Derby 30 min Away ~ Bourbon Trail ~ Hot Tu

RachelRating, 5 stars3 weeks ago
Nice and clean place. The train at night was a bit annoying, went through a couple different times. So bring some earplugs if possible. But we did get use to it. We had a blast listening to the record player one night over a drink. The hot tub was great , especially on the rainy colder days of the trip. We would definitely recommend and stay again. If and when we plan another trip to Kentucky. Thanks!
Top Guest favourite
Cottage in Simpsonville
5 out of 5 average rating, 35 reviews

Miles Around KY Cottage-Hot Tub

TaylorRating, 5 stars3 weeks ago
Lovely location, loved the space, the back porch was such a lovely way to end the day with the hot tub. Super responsive, and a great central location to the bourbon trail! Definitely will stay here again when we visit this side of KY!
Top Guest favourite
Cottage in Taylorsville
4.96 out of 5 average rating, 195 reviews

Luxury Retreat with Hot Tub

GretchenRating, 5 stars3 weeks ago
Such an awesome place to stay for our wedding weekend. Thank you so much.
Top Guest favourite
Cottage in Taylorsville
4.99 out of 5 average rating, 136 reviews

Lakeside Cottage -upgraded hot tub- Bourbon Trail!

KristenRating, 5 stars6 months ago
After the recent passing of my Mom, I needed a getaway to relax , unwind and clear my head . I wanted someplace cozy and private, surrounded by nature. I knew nothing of the area but was very pleased. So quite and relaxing. SUPER clean, very impressive, no details overlooked. While relaxing in the hot tub, you could hear an owl calling in the distance. Exactly what I needed. Thank you for sharing your beautiful cottage with us.
Cottage in Taylorsville
4.84 out of 5 average rating, 132 reviews

Mint Julep Cottage near Louisville & Bourbon Trail

JulieRating, 5 stars2 weeks ago
Cute cottage perfect for a weekend getaway. Close to the playground for the kids.
Cottage in Taylorsville
4.64 out of 5 average rating, 74 reviews

Splash of 7&7

AlexandreaRating, 5 stars1 month ago
I used this cottage to prepare for my wedding. It had great spaces for several people to get ready including a large area in the master bedroom upstairs. The wedding venue was right across the street. We stayed here for the weekend so we could setup and take down without having to rush. The jacuzzi out back was clean and private. The home was beautiful and comfortable. I would highly recommend!
Guest favourite
Cottage in Taylorsville
4.93 out of 5 average rating, 74 reviews

Little Beauty, lake cottage, near Louisville.

JenRating, 5 stars3 weeks ago
We loved the warm welcome of flowers, snacks, waters, and bourbon gift basket. Everything was spotless and very homey. We had plenty of room in the kitchen and appreciated all of the different types of glasses etc for drinking and eating. We enjoyed our stay very much and appreciated all of the thought and time that went into making this cottage a great vacation retreat for the two of us.

Pet-friendly cottage rentals

Cottage in Prospect
4.29 out of 5 average rating, 14 reviews

Spacious Prospect Cottage w/ Deck & Scenic Views

JessiRating, 5 stars4 months ago
Great Experience. The house had a beautiful view of a creek and had plenty of room for entertaining. Very clean and well kept, I would definitely stay here again.
Top Guest favourite
Cottage in Willisburg
4.99 out of 5 average rating, 71 reviews

A Romantic Getaway on the Bourbon Trail

LisaRating, 5 stars1 month ago
This place is a little out of way, but so peaceful and beautiful scene. Very comfortable bed! Judith checked in a couple times via email to see if we needed anything, but we really had everything we needed. It was one of the best for us.
Cottage in Taylorsville
4.84 out of 5 average rating, 111 reviews

Shore Thing Bourbon Trail Lodging #20

JakeRating, 5 stars3 months ago
We’ve stayed here several times over the last few years and we plan on continuing to do so on our annual Kentucky trip.
Superhost
Cottage in Bardstown
4.72 out of 5 average rating, 306 reviews

Bourbon Oak Smokehouse Cottage

ErinRating, 5 stars1 week ago
Perfect for our weekend stay as we explored nearby distilleries. Quiet, tucked away place with lots of charm.
Guest favourite
Cottage in New Pekin
4.95 out of 5 average rating, 43 reviews

Toad Stop Cottage in New Pekin, Indiana

LaurenRating, 5 stars3 months ago
Such a peaceful, quint place! Julia and her family were perfect hosts…will definitely be back!
Cottage in Louisville
4.78 out of 5 average rating, 23 reviews

2 Mi to Churchill Downs: Louisville Home!

ChrisRating, 5 stars8 months ago
This is a good spot and was worth the price. It had everything our group needed and made for a comfy stay. The only things that I have that are even kind of negative are the lack of a few cleaning/trash supplies (no big deal, the host was graciously okay with us just piling stuff near the trash can on our way out) and the kind of creepy basement. But overall excellent place, exactly what you want out of a BnB in Louisville.
Cottage in Spencer County
4.56 out of 5 average rating, 48 reviews

Shore Thing Bourbon Trail Lodging #21

TammyRating, 5 stars1 month ago
The place was beautiful, peaceful, and had everything we needed. The hot tub was hot and ready for us and we could see the lake from the house. We enjoyed cooking in the beautiful kitchen, soaking in the hot tub, and making our way to the lake to fish. We ate at Cattlemans Roadhouse nearby which was great as well. Great weekend getaway.
Superhost
Cottage in Taylorsville
4.82 out of 5 average rating, 109 reviews

Lake Livin' & Bourbon Sippin'

ChristopherRating, 5 stars3 weeks ago
Great host and stay. Highly recommend

Private cottage rentals

Superhost
Cottage in Prospect
4.93 out of 5 average rating, 14 reviews

The Woodlands: a new cottage nestled in the woods.

TylerRating, 5 stars4 months ago
Perfect! The pictures do not do justice for this place. It was such a nice and cozy cottage. We felt so much at home. We were only about 12 minutes from town to go get dinner one night and a beautiful country drive there.. The rest of all the meals we cooked in the house and everything was there we needed. We did not want to even leave. We came down to visit the farm machinery show and tractor pull at the fairgrounds. It was a nice easy drive there. So nice to get out of the busy area to such a beautiful home and farm. We felt so safe. It rained the whole weekend, but enjoyed the cottage from the inside listening to the rain and thunder. Everything was so nice. We enjoyed looking through the books throughout the house. It was updated with new but still felt like you were in the original era of the house. I cant say enough how much we loved this place and can't wait to go back!
Cottage in Taylorsville
4.7 out of 5 average rating, 73 reviews

"On the Rocks" Bourbon Trail Getaway

DavidRating, 5 stars1 month ago
We loved our stay here and Cliff was wonderful. We were three couples and there was plenty of room. This house is larger than it appears from the pictures. We had an issue with the gate code being different than what we were given but Cliff was instantly available, very nice, and got us in. It's a beautiful home and we'd stay there again. Very quiet, places to walk, and clean. I think if you switched the bunk beds with a Queen sized bed from downstairs it would be set up better for Adult couples. Thanks so much for our stay and we loved our Kentucky trip!
Guest favourite
Cottage in Louisville
4.9 out of 5 average rating, 86 reviews

The Paddock Carriage House

JenniferRating, 5 stars2 weeks ago
Very easy to find. Friendly gentleman, will go back again.
Top Guest favourite
Cottage in Floyds Knobs
5 out of 5 average rating, 73 reviews

Tranquil setting with breathtaking views

AudyRating, 5 stars1 month ago
Thanks for the stay. Very unique. Pretty amazing view.
Guest favourite
Cottage in Spencer County
5 out of 5 average rating, 20 reviews

LAKE COTTAGE, near Louisville & the Bourbon Trail

BrianRating, 5 stars5 months ago
Meg goes above and beyond!!! Not only does she have the best view of the lake, the accommodations are impeccable from the screened in porch to the hot tub to the adorable kitchen and amazing sleeping accommodations!!! Every other cottage on Taylorsville pales in comparison!!! If you have not been, you need to check it out!!! There is a peacefulness and tranquillity that you immediately get as soon as you open the door to the #17.
Guest favourite
Cottage in Jeffersonville
4.89 out of 5 average rating, 74 reviews

Peaceful Easy Feeling

AlanaRating, 5 stars8 months ago
The place was very nice. Very clean and quiet. Loved how peaceful it was the entire time. Can’t wait to come back and stay again.
Superhost
Cottage in Bardstown
4.9 out of 5 average rating, 405 reviews

Bardstown Coppersmith Cottage

MaxRating, 5 stars4 weeks ago
Cute cottage right in Bardstown, really reminds you of how it was probably like hundreds of years ago, in a good way!
Guest favourite
Cottage in Bardstown
4.95 out of 5 average rating, 204 reviews

McIntyre’s Country Cottage

EllieRating, 5 stars3 weeks ago
It was great and the owners are so kind and very helpful. I would definitely stay here again and beautiful surroundings.

Destinations to explore