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Pleasureville Holiday Rentals

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Our top choices for Pleasureville holiday rentals

1. Unique Downtown Studio with an Industrial Vibe

Unique Downtown Studio with an Industrial Vibe
Shelbyville
10.0 out of 10, Exceptional, (34 reviews)
"Wonderful location in a very nice small town. Grocery store, coffee shop and many other amenities close by.The property was very spacious and well done for 2 people."
United States
Kathleen S.
The price is NZ$304
includes taxes & fees
18 Nov - 19 Nov
Unique Downtown Studio with an Industrial Vibe

2. Capital City Condo #5 Close to Water Park and Restaurants

Capital City Condo #5 Close to Water Park and Restaurants
Frankfort
8.6 out of 10, Excellent, (27 reviews)
"Quiet, affordable, nice local get away. Would book again."
United States
SANDRA
The price is NZ$281
includes taxes & fees
15 Nov - 16 Nov
Capital City Condo #5 Close to Water Park and Restaurants

3. Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
Shelbyville
10.0 out of 10, Exceptional, (22 reviews)
"The Stables suite was perfect for an extended stay in Shelbyville. Great location and wonderful place to stay. "
United States
Kim K.
The price is NZ$314
includes taxes & fees
30 Nov - 1 Dec
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

4. Capital City Condo #1 close to Interstate, Water Park, Restaurants and Shopping

Capital City Condo #1 close to Interstate, Water Park, Restaurants and Shopping
Frankfort
8.8 out of 10, Excellent, (92 reviews)
"It was a nice stay"
United States
Teresa M.
The price is NZ$280
includes taxes & fees
24 Nov - 25 Nov
Capital City Condo #1 close to Interstate, Water Park, Restaurants and Shopping

5. Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views

Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views
Waddy
9.0 out of 10, Wonderful, (12 reviews)
"Excellent stay and a beautiful property. Perfect for our needs no complaints."
United States
Anthony T.
The price is NZ$676
includes taxes & fees
16 Nov - 17 Nov
Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views

6. Bourbon Barrel Cabin B. There are 2 cabins available A & B. Brand new Cabins.

Bourbon Barrel Cabin B. There are 2 cabins available A & B. Brand new Cabins.
Frankfort
9.6 out of 10, Exceptional, (26 reviews)
"What a great cabin it was so clean and cute and had everything that we needed a great place to stay"
United States
Jessica S.
The price is NZ$466
includes taxes & fees
27 Nov - 28 Nov
Bourbon Barrel Cabin B. There are 2 cabins available A & B. Brand new Cabins.

7. Capital City Condo #10

Capital City Condo #10
Frankfort
8.2 out of 10, Very good, (10 reviews)
"Such a great little place. Hosts are wonderful!"
United States
Amanda L.
The price is NZ$280
includes taxes & fees
15 Nov - 16 Nov
Capital City Condo #10

8. Capital City Condo #8

Capital City Condo #8
Frankfort
8.6 out of 10, Excellent, (43 reviews)
"This was our third time staying at this place for a bourbon trip. Overall it is a good value, has the basics and close to distilleries. "
United States
Robert V.
The price is NZ$280
includes taxes & fees
27 Nov - 28 Nov
Capital City Condo #8

9. This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.

This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.
Frankfort
8.8 out of 10, Excellent, (78 reviews)
"The house is clean and cute. Beds are very comfortable. Bathroom is tight and the wifi didn't work. The outside could use some work. Trees need to be trimmed, window screens were broken, etc. Conveniently located around everything and very much enjoyed our stay."
United States
Nick K.
The price is NZ$270
includes taxes & fees
16 Nov - 17 Nov
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.

10. Capital City Condo #2

Capital City Condo #2
Frankfort
9.2 out of 10, Wonderful, (81 reviews)
"We had a great stay!!! Great location for the bourbon trail and other attractions!!"
United States
Renee L.
Capital City Condo #2

11. The Bourbon Garage- walking distance to Buffalo Trace!

The Bourbon Garage- walking distance to Buffalo Trace!
Frankfort
9.8 out of 10, Exceptional, (40 reviews)
"What a great location for bourbon lovers who want to spend the day close to the distilleries! The apt was perfect & offered all of the comforts of home. Would definitely stay again!"
United States
Susan H.
The price is NZ$416
includes taxes & fees
13 Dec - 14 Dec
The Bourbon Garage- walking distance to Buffalo Trace!

12. Kentucky Bourbon Trail: Hot Tub & Game Room

Kentucky Bourbon Trail: Hot Tub & Game Room
Bagdad
10.0 out of 10, Exceptional, (26 reviews)
"Such a beautiful, peaceful area and the cutest home! It was perfect for our large group and Iris was an incredible host. We definitely want to visit again!"
United States
Hannah G.
The price is NZ$1,009
includes taxes & fees
17 Nov - 18 Nov
Kentucky Bourbon Trail: Hot Tub & Game Room

13. Rustic Container Cabin on Beautiful Farm - Near Ark & Bourbon Trail

Rustic Container Cabin on Beautiful Farm - Near Ark & Bourbon Trail
Owenton
9.4 out of 10, Exceptional, (92 reviews)
"Such a great stay & getaway with my pups! The property is so nice and cozy for what we needed! Wonderful and helpful host too! We’ll be back "
United States
Mary S.
The price is NZ$201
includes taxes & fees
15 Nov - 16 Nov
Rustic Container Cabin on Beautiful Farm - Near Ark & Bourbon Trail

14. Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.

Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.
Frankfort
8.8 out of 10, Excellent, (110 reviews)
"It was a great place to stay & conveniently located to lots of restaurants & distilleries."
United States
Darby D.
The price is NZ$280
includes taxes & fees
27 Nov - 28 Nov
Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.

15. Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby

Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
Shelbyville
9.4 out of 10, Exceptional, (51 reviews)
"Great house and location. Enjoyed our stay. Would use this location again."
United States
Donald A.
The price is NZ$483
includes taxes & fees
15 Nov - 16 Nov
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby

16. Capital City Condo #4

Capital City Condo #4
Frankfort
8.8 out of 10, Excellent, (61 reviews)
"Great property, Great host, Great experience, will stay again!!!"
United States
Christopher R.
The price is NZ$281
includes taxes & fees
28 Nov - 29 Nov
Capital City Condo #4

17. Vintage Camper Cabin on Beautiful Farm Near Ark & Bourbon Trail

Vintage Camper Cabin on Beautiful Farm Near Ark & Bourbon Trail
Owenton
9.4 out of 10, Exceptional, (18 reviews)
"If you’re looking for a quiet place to relax this is it. Josh was so pleasant to work with."
United States
Teresa I.
The price is NZ$176
includes taxes & fees
15 Nov - 16 Nov
Vintage Camper Cabin on Beautiful Farm Near Ark & Bourbon Trail

18. This apartment is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.

This apartment is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.
Frankfort
9.4 out of 10, Exceptional, (13 reviews)
"Excellent location with many shops and restaurants within walking distance."
United States
Mark S.
The price is NZ$323
includes taxes & fees
15 Nov - 16 Nov
This apartment is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.

19. Capital City Condo #3

Capital City Condo #3
Frankfort
8.2 out of 10, Very good, (43 reviews)
"Our stay was great. The price was good for the type place it was. Our host was friendly and so helpful, even bringing the best donuts to us our first morning there. It was very convenient to Buffalo Trace Distillery and a nice drive to Churchill Downs."
United States
Margie B.
Capital City Condo #3

20. Scenic Highgrounds Modern Cabin - Chicory

Scenic Highgrounds Modern Cabin - Chicory
Frankfort
9.8 out of 10, Exceptional, (8 reviews)
"Great place to stay, beautiful scenery! just far enough out of the city! Would definitely stay there again."
United States
Rob L.
The price is NZ$492
includes taxes & fees
15 Nov - 16 Nov
Scenic Highgrounds Modern Cabin - Chicory
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pleasureville Hotel Reviews

Find out more about Pleasureville

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Pleasureville holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Pleasureville. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Pleasureville. Seeing all the best attractions is bound to make you fall in love with Pleasureville. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Pleasureville short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Pleasureville?

Yes, there are holiday rentals close to the most popular sights in Pleasureville, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Pleasureville has to offer?

Charming 2-bedroom house on our farm with beautiful sunsets: This holiday home rental outside of Pleasureville is located in a rural location, and offers a BBQ, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Pleasureville?

Explore the area and family-friendly sights such as La Grange Railroad Museum & Learning Center, or get out into nature at a spot like Ohio River Valley. In the wider area, you’ll find Bulleit Distilling Co. and Jeptha Creed Distillery.

What are holiday rentals like in Pleasureville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pleasureville. Holiday rentals feature amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for a family trip.