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Pleasureville Holiday Rentals

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Our top choices for Pleasureville holiday rentals

1. 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, (21 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$325
includes taxes & fees
5 Oct - 6 Oct
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

2. Unique Downtown Studio with an Industrial Vibe

Unique Downtown Studio with an Industrial Vibe
Shelbyville
10.0 out of 10, Exceptional, (32 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$349
includes taxes & fees
28 Oct - 29 Oct
Unique Downtown Studio with an Industrial Vibe

3. 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, (24 reviews)
"The place was gorgeous, beautifully set up and easy to get to. We were disappointed that we were unable to enjoy the outdoors due to the level of humidity. We recommend this place and we hope to stay here again for our future visits."
United States
Terry-Ann
The price is NZ$434
includes taxes & fees
7 Oct - 8 Oct
Bourbon Barrel Cabin B. There are 2 cabins available A & B. Brand new Cabins.

4. Sip on bourbon in the hot tub! +hiking & game shed

Sip on bourbon in the hot tub! +hiking & game shed
Frankfort
9.4 out of 10, Exceptional, (6 reviews)
"Family friendly"
United States
Michael I.
The price is NZ$790
includes taxes & fees
7 Oct - 8 Oct
Sip on bourbon in the hot tub! +hiking & game shed

5. Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill

Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill
Frankfort
9.8 out of 10, Exceptional, (28 reviews)
"Our stay was amazing! Beautiful porch for sitting outside on a rainy Kentucky night in late spring. The spa was delightful as well when it was raining. We stayed with our daughter and son in law, we look forward to bringing friends with us in the future."
United States
Laura O.
The price is NZ$1,427
includes taxes & fees
19 Oct - 20 Oct
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill

6. The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade Barn, Sleeps 12+

The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade Barn, Sleeps 12+
Shelbyville
9.8 out of 10, Exceptional, (10 reviews)
"Stay was great, the place was perfect, and the view was beautiful."
United States
Bobby E.
The price is NZ$900
includes taxes & fees
4 Oct - 5 Oct
The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade Barn, Sleeps 12+

7. Beautiful restored Victorian farmhouse

Beautiful restored Victorian farmhouse
Shelbyville
9.2 out of 10, Wonderful, (15 reviews)
"Lovely place, great outdoor seating areas, and spacious rooms."
United States
Joann E.
The price is NZ$779
includes taxes & fees
1 Oct - 2 Oct
Beautiful restored Victorian farmhouse

8. 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$695
includes taxes & fees
13 Oct - 14 Oct
Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views

9. *NEW* UNIQUE HOME: HOT TUB-SAUNA-FIREPIT-GAME ROOM-SPEAKEASY-INGROUND POOL-6 BEDS/5 BATHS-5 KING BEDS

*NEW* UNIQUE HOME: HOT TUB-SAUNA-FIREPIT-GAME ROOM-SPEAKEASY-INGROUND POOL-6 BEDS/5 BATHS-5 KING BEDS
Bagdad
9.6 out of 10, Exceptional, (7 reviews)
"We had a fantastic holiday weekend at this property - Two families (4 adults, 4 kids) stayed with plenty of room and amenities. This house could have easily slept more. Communication from the host was clear and prompt. The kids absolutely loved the game room and adults enjoyed the ample living spaces on both the main floor and the basement. Although we didn't use the pool given the time of year, the hot tub, sauna, and fire pit were great! Our kids loved seeing the horses all around...
United States
Justin C.
The price is NZ$1,919
includes taxes & fees
12 Oct - 13 Oct
*NEW* UNIQUE HOME: HOT TUB-SAUNA-FIREPIT-GAME ROOM-SPEAKEASY-INGROUND POOL-6 BEDS/5 BATHS-5 KING BEDS

10. 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)
"Perfect location for the Bourbon Trail. Nice, clean, and affordable. 10 out of 10, would do it again!"
United States
Dwight K.
The price is NZ$291
includes taxes & fees
1 Oct - 2 Oct
Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.

11. 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.
Capital City Condo #10

12. 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, (50 reviews)
"Great house and location. Enjoyed our stay. Would use this location again."
United States
Donald A.
The price is NZ$532
includes taxes & fees
25 Oct - 26 Oct
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby

13. 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$291
includes taxes & fees
4 Oct - 5 Oct
Capital City Condo #1 close to Interstate, Water Park, Restaurants and Shopping

14. Scenic Highgrounds Modern Cabin - Chicory

Scenic Highgrounds Modern Cabin - Chicory
Frankfort
9.8 out of 10, Exceptional, (8 reviews)
"Great place for a quiet getaway."
United States
john w.
The price is NZ$525
includes taxes & fees
4 Oct - 5 Oct
Scenic Highgrounds Modern Cabin - Chicory

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

The Bourbon Garage- walking distance to Buffalo Trace!
Frankfort
10.0 out of 10, Exceptional, (33 reviews)
"Great property and wonderful hosts! "
United States
Jacinda C.
The price is NZ$437
includes taxes & fees
26 Oct - 27 Oct
The Bourbon Garage- walking distance to Buffalo Trace!

16. 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$291
includes taxes & fees
1 Oct - 2 Oct
Capital City Condo #8

17. Renovated 3 bedroom, 2.5 bath 1,900 sq ft home with finished walkout basement

Renovated 3 bedroom, 2.5 bath 1,900 sq ft home with finished walkout basement
La Grange
10.0 out of 10, Exceptional, (9 reviews)
"Very nice house, spacious, clean and very comfortable. Perfect for our stay to attend a conference in the area. Highly recommend!!"
United States
Jessica B.
The price is NZ$926
includes taxes & fees
1 Oct - 2 Oct
Renovated 3 bedroom, 2.5 bath 1,900 sq ft home with finished walkout basement

18. Luxury farmhouse on Bourbon Trail with hot tub - Bulleit 4 mi - Frankfort 15 mi

Luxury farmhouse on Bourbon Trail with hot tub - Bulleit 4 mi - Frankfort 15 mi
Bagdad
10.0 out of 10, Exceptional, (17 reviews)
"Great location and very clean. Plenty of room to spread out and relax. Carrie is a Professional and thoughtful host!!"
United States
David S.
The price is NZ$1,331
includes taxes & fees
7 Oct - 8 Oct
Luxury farmhouse on Bourbon Trail with hot tub - Bulleit 4 mi - Frankfort 15 mi

19. Off to the Races Retreat - Hidden Clues Inside

Off to the Races Retreat - Hidden Clues Inside
Frankfort
10.0 out of 10, Exceptional, (11 reviews)
"Great place! "
United States
Brad S.
The price is NZ$405
includes taxes & fees
12 Oct - 13 Oct
Off to the Races Retreat - Hidden Clues Inside

20. This gem sits in the heart of picturesque South Frankfort, near the Kentucky river

This gem sits in the heart of picturesque South Frankfort, near the Kentucky river
Frankfort
8.6 out of 10, Excellent, (12 reviews)
"We had the best time! Second time staying at this location - first time was on the first floor. A great location and very welcoming! We'll be back!"
United States
Melissa R.
The price is NZ$368
includes taxes & fees
26 Oct - 27 Oct
This gem sits in the heart of picturesque South Frankfort, near the Kentucky river
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.