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Holiday Homes in Pleasureville

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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 homes

A modern kitchen with a dining area, built-in shelves, and a green sofa in the living room.

1. Quiet Downtown Maple Cottage Gem

Quiet Downtown Maple Cottage Gem
Shelbyville
10.0 out of 10, Exceptional, (1 review)
"Very convenient for Horse Show we were attending. Everything was as described and the hosts were very accommodating. "
United States
Marlena J.
The price is NZ$605
includes taxes & fees
5 Oct - 6 Oct
Quiet Downtown Maple Cottage Gem
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a marble countertop.

2. 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$670
includes taxes & fees
26 Oct - 27 Oct
Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views
A living room with a beige sofa, a brown leather chair, a coffee table, and a ceiling fan.

3. Beautiful New 2-Bedroom Villa with Stunning Rolling-Hill Views

Beautiful New 2-Bedroom Villa with Stunning Rolling-Hill Views
Waddy
The price is NZ$530
includes taxes & fees
26 Oct - 27 Oct
Beautiful New 2-Bedroom Villa with Stunning Rolling-Hill Views
A modern kitchen with a central island, stainless steel appliances, and a large window providing natural light.

4. Ridge View Villa #1 -Haven in the Heart of the Bourbon Trail.

Ridge View Villa #1 -Haven in the Heart of the Bourbon Trail.
Waddy
10.0 out of 10, Exceptional, (2 reviews)
"The place was great. Tucked away off the main highway and between bourbon country’s best. Well stocked amenities and little things provided that were a great touch. Will be back again!"
United States
Daniel H.
The price is NZ$487
includes taxes & fees
4 Oct - 5 Oct
Ridge View Villa #1 -Haven in the Heart of the Bourbon Trail.
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

5. Haven of the Bluegrass | Bourbon Trail Getaway!

Haven of the Bluegrass | Bourbon Trail Getaway!
Shelbyville
The price is NZ$757
includes taxes & fees
5 Oct - 6 Oct
Haven of the Bluegrass | Bourbon Trail Getaway!
A house with a covered porch, outdoor seating, and a grill area.

6. Your Kentucky Bourbon Trail stay hosted by Sixteen Chairs with panoramic horse country views, barrel sauna, cold plunge, hot tub, gym, game room, theatre room, and dedicated outdoor space

Your Kentucky Bourbon Trail stay hosted by Sixteen Chairs with panoramic horse country views, barrel sauna, cold plunge, hot tub, gym, game room, theatre room, and dedicated outdoor space
Shelbyville
The price is NZ$1,306
includes taxes & fees
4 Oct - 5 Oct
Your Kentucky Bourbon Trail stay hosted by Sixteen Chairs with panoramic horse country views, barrel sauna, cold plunge, hot tub, gym, game room, theatre room, and dedicated outdoor space
A two-story house with a porch, a small garden, and a sign that reads "Hotel."

7. 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
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and pendant lighting.

8. 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
A wooden coffee table with three bottles and a glass container in a living room.

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, (76 reviews)
"Great stay! "
United States
Armando G.
The price is NZ$280
includes taxes & fees
1 Oct - 2 Oct
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.
A modern kitchen with white cabinetry, stainless steel appliances, and a granite countertop.

10. the bourbon barrel escape HotTub Game Room pets ok

the bourbon barrel escape HotTub Game Room pets ok
Shelbyville
The price is NZ$959
includes taxes & fees
19 Oct - 20 Oct
the bourbon barrel escape HotTub Game Room pets ok
A hotel room with two beds, a nightstand, a lamp, and plaid-patterned walls.

11. University Stay | Sleeps 10 | Game Room + Firepit + Grill

University Stay | Sleeps 10 | Game Room + Firepit + Grill
Frankfort
The price is NZ$618
includes taxes & fees
19 Oct - 20 Oct
University Stay | Sleeps 10 | Game Room + Firepit + Grill
A swimming pool with a deck area, outdoor seating, and a covered patio with string lights.

12. *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$1,587
includes taxes & fees
1 Oct - 2 Oct
*NEW* UNIQUE HOME: HOT TUB-SAUNA-FIREPIT-GAME ROOM-SPEAKEASY-INGROUND POOL-6 BEDS/5 BATHS-5 KING BEDS
A white building with a porch, columns, and a covered entrance.

13. 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
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.

14. 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
A modern kitchen with stainless steel appliances, a built-in oven, and a microwave.

15. 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
A living room with a sectional sofa, a dining table, and a ceiling fan.

16. Peaceful 6-bedroom house in charming Bagdad

Peaceful 6-bedroom house in charming Bagdad
Bagdad
The price is NZ$2,169
includes taxes & fees
6 Oct - 7 Oct
Peaceful 6-bedroom house in charming Bagdad
A large, multi-story house with a central driveway and a pond in the background.

17. Bourbon Trail Lakehouse

Bourbon Trail Lakehouse
Frankfort
9.6 out of 10, Exceptional, (64 reviews)
"Great place to stay!"
United States
Jeff S.
The price is NZ$552
includes taxes & fees
20 Oct - 21 Oct
Bourbon Trail Lakehouse
A dining area with a wooden table, chairs, a bench, a chandelier, and framed artwork on the walls.

18. Spacious Bourbon retreat near Downtown Louisville!

Spacious Bourbon retreat near Downtown Louisville!
Simpsonville
The price is NZ$796
includes taxes & fees
19 Oct - 20 Oct
Spacious Bourbon retreat near Downtown Louisville!
A compact kitchen with a refrigerator, stove, microwave, and coffee maker. There is a dining area with chairs and a table.

19. Miss Reba's Love is a charming house with a warm Kentucky feel.

Miss Reba's Love is a charming house with a warm Kentucky feel.
Frankfort
10.0 out of 10, Exceptional, (10 reviews)
"Very clean and communication with host was excellent. Would recommend to anyone. "
United States
Chuck F.
The price is NZ$583
includes taxes & fees
6 Oct - 7 Oct
Miss Reba's Love is a charming house with a warm Kentucky feel.
A hot tub with a glass of red wine, surrounded by a lush green outdoor setting.

20. Bourbon Trail! Game Room Hot Tub Speakeasy FirePit

Bourbon Trail! Game Room Hot Tub Speakeasy FirePit
Shelbyville
10.0 out of 10, Exceptional, (23 reviews)
"Great location perfect house to enjoy"
United States
tim d.
The price is NZ$1,112
includes taxes & fees
5 Oct - 6 Oct
Bourbon Trail! Game Room Hot Tub Speakeasy FirePit
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

Hampton Inn Simpsonville

Hampton Inn Simpsonville

10/10 Excellent
"We loved our stay here! The room was neat and comfortable, it was clean. This is a new or newly renovated facility. The staff was very friendly and helpful. We definitely would stay here again!"
Jon 1-night trip
Posted 3 hours ago
Hampton Inn Simpsonville

Find out more about Pleasureville

Pleasureville Holiday Homes information

Number of reviews
283
Accommodation
202 Holiday Homes
Lowest Price
NZ$280
Highest Price
NZ$2,169