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Pleasureville Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Pleasureville holiday rentals

A living room with a TV, a wooden entertainment unit, a round coffee table, and a sofa.

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 HK$745
HK$1,437 total
includes taxes & fees
4 Oct - 5 Oct
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
A bar area with a black bar counter, stools, and a large horseshoe-shaped metal object on the wall.

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 HK$753
HK$1,446 total
includes taxes & fees
7 Oct - 8 Oct
Unique Downtown Studio with an Industrial Vibe
A modern cabin with a wooden deck and a balcony, surrounded by a natural landscape.

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 HK$1,098
HK$1,984 total
includes taxes & fees
7 Oct - 8 Oct
Bourbon Barrel Cabin B. There are 2 cabins available A & B. Brand new Cabins.
A log cabin with a fire pit and outdoor seating.

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 HK$1,873
HK$3,273 total
includes taxes & fees
11 Oct - 12 Oct
Sip on bourbon in the hot tub! +hiking & game shed
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and pendant lighting.

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.
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill
A log cabin with a covered porch, large windows, and a well-maintained front yard.

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 HK$3,177
HK$4,043 total
includes taxes & fees
4 Oct - 5 Oct
The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade Barn, Sleeps 12+
A kitchen with grey cabinets, a large island, pendant lighting, and a view of the outdoors.

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 HK$1,730
HK$3,497 total
includes taxes & fees
13 Oct - 14 Oct
Beautiful restored Victorian farmhouse
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a marble countertop.

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 HK$926
HK$2,696 total
includes taxes & fees
19 Oct - 20 Oct
Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views
A swimming pool with a deck area, outdoor seating, and a covered patio with string lights.

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 HK$2,581
HK$7,199 total
includes taxes & fees
4 Oct - 5 Oct
*NEW* UNIQUE HOME: HOT TUB-SAUNA-FIREPIT-GAME ROOM-SPEAKEASY-INGROUND POOL-6 BEDS/5 BATHS-5 KING BEDS
A living room with a sofa, a coffee table, a rug, and a bookshelf.

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 HK$549
HK$1,292 total
includes taxes & fees
1 Oct - 2 Oct
Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.
A reception area with a mounted TV displaying various streaming services, a wooden console with a welcome sign, and a seating area with a table and chairs.

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.
The price is HK$549
HK$1,292 total
includes taxes & fees
5 Oct - 6 Oct
Capital City Condo #10
A two-story house with a porch, a small garden, and a sign that reads "Hotel."

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 HK$1,208
HK$2,261 total
includes taxes & fees
25 Oct - 26 Oct
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
A modern living room with a TV mounted on the wall, a wooden console table, a floor lamp, a potted plant, and a basket.

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 HK$549
HK$1,292 total
includes taxes & fees
4 Oct - 5 Oct
Capital City Condo #1 close to Interstate, Water Park, Restaurants and Shopping
A modern cabin with a wooden deck, a covered outdoor seating area, and a bright orange door.

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 HK$1,223
HK$2,433 total
includes taxes & fees
13 Oct - 14 Oct
Scenic Highgrounds Modern Cabin - Chicory
A modern living room with a sofa, a coffee table, and a bed.

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 HK$819
HK$1,933 total
includes taxes & fees
26 Oct - 27 Oct
The Bourbon Garage- walking distance to Buffalo Trace!
A beige sofa with patterned cushions, a dark patterned rug, and a window with blinds.

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 HK$549
HK$1,292 total
includes taxes & fees
1 Oct - 2 Oct
Capital City Condo #8
A modern kitchen with stainless steel appliances, a built-in oven, and a microwave.

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 HK$1,451
HK$3,928 total
includes taxes & fees
1 Oct - 2 Oct
Renovated 3 bedroom, 2.5 bath 1,900 sq ft home with finished walkout basement
A white building with a porch, columns, and a covered entrance.

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 HK$3,050
HK$6,128 total
includes taxes & fees
7 Oct - 8 Oct
Luxury farmhouse on Bourbon Trail with hot tub - Bulleit 4 mi - Frankfort 15 mi
A modern living room with a round coffee table, a sofa with numbered cushions, a dining area with striped curtains, and a chandelier with red flowers.

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 HK$981
HK$1,828 total
includes taxes & fees
12 Oct - 13 Oct
Off to the Races Retreat - Hidden Clues Inside
A room with a large open door leading to a balcony with a view of houses. There is a small table and chairs on the balcony.

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 HK$816
HK$1,665 total
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

Holiday Inn Express & Suites La Grange by IHG

Holiday Inn Express & Suites La Grange by IHG

8/10 Good
"The ice machine was out of order and the pool was out of order"
Alton 3-night trip
Posted 3 hours ago
Holiday Inn Express & Suites La Grange by IHG

Find out more about Pleasureville

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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.