Holiday Homes in Pleasureville

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Cabins
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Apartments
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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Pleasureville holiday homes

A fire pit with chairs around it in a grassy outdoor area.

1. Haven of the Bluegrass | Bourbon Trail Getaway!

Haven of the Bluegrass | Bourbon Trail Getaway!
Shelbyville
The price is NZ$787
includes taxes & fees
29 Nov - 30 Nov
Haven of the Bluegrass | Bourbon Trail Getaway!
A porch with two wooden chairs and a table, white siding, and a window.

2. The Shelby House | Historic Charm, Modern Comfort

The Shelby House | Historic Charm, Modern Comfort
Shelbyville
The price is NZ$477
includes taxes & fees
15 Nov - 16 Nov
The Shelby House | Historic Charm, Modern Comfort
A living room with a large TV mounted on the wall displaying a race track, a wooden cabinet with glass doors, a dining area with a table and chairs, and a small side table with a radio.

3. 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
An outdoor patio with wicker furniture, a central fire pit, and string lights.

4. 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$988
includes taxes & fees
17 Nov - 18 Nov
Kentucky Bourbon Trail: Hot Tub & Game Room
A modern kitchen with black cabinets, a central island, and wooden shelves above a textured backsplash.

5. 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$595
includes taxes & fees
15 Nov - 16 Nov
Quiet Downtown Maple Cottage Gem
A white building with a porch and four white Adirondack chairs facing a grassy field.

6. 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$468
includes taxes & fees
24 Nov - 25 Nov
Ridge View Villa #1 -Haven in the Heart of the Bourbon Trail.
A modern kitchen with white cabinets, a marble floor, a farmhouse-style accent wall, and a kitchen island with a towel rack.

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, (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
A house with a covered porch, outdoor seating, and a grill area.

8. Bourbon Trail | 4BR, Sleeps 10, Barrel Sauna, Hot Tub, Gym, Game Room, Fire Pits

Bourbon Trail | 4BR, Sleeps 10, Barrel Sauna, Hot Tub, Gym, Game Room, Fire Pits
Shelbyville
Bourbon Trail | 4BR, Sleeps 10, Barrel Sauna, Hot Tub, Gym, Game Room, Fire Pits
A wooden deck with a view of a cityscape, a wooden bench, and a table with chairs.

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.
A modern kitchen with a central island, stainless steel appliances, and a blue accent wall.

10. 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$534
includes taxes & fees
30 Nov - 1 Dec
Beautiful New 2-Bedroom Villa with Stunning Rolling-Hill Views
A living room with a brick wall, a ceiling fan, a sofa, an orange chair, and a painting.

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

University Stay | Sleeps 10 | Game Room + Firepit + Grill
Frankfort
University Stay | Sleeps 10 | Game Room + Firepit + Grill
A wooden shelf with framed artwork, a thank you box, and a remote control.

12. 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, (11 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$900
includes taxes & fees
15 Nov - 16 Nov
Renovated 3 bedroom, 2.5 bath 1,900 sq ft home with finished walkout basement
A covered deck with a railing, a white building with large windows, and a metal roof.

13. Spacious Bourbon retreat near Downtown Louisville!

Spacious Bourbon retreat near Downtown Louisville!
Simpsonville
The price is NZ$849
includes taxes & fees
15 Nov - 16 Nov
Spacious Bourbon retreat near Downtown Louisville!
A swimming pool with a deck area, outdoor seating, and a covered patio with string lights.

14. *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
9.8 out of 10, Exceptional, (11 reviews)
"My family & I had a great time at the house. My grandkids loved the pool. It was a very enjoyable stay."
United States
LORI T.
The price is NZ$1,562
includes taxes & fees
17 Nov - 18 Nov
*NEW* UNIQUE HOME: HOT TUB-SAUNA-FIREPIT-GAME ROOM-SPEAKEASY-INGROUND POOL-6 BEDS/5 BATHS-5 KING BEDS
A porch with white rocking chairs and a wooden floor.

15. 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, (30 reviews)
"Beautiful and spacious! The host has thought of absolutely everything. We had a wonderfully relaxing time and the beds are SUPER comfortable! It's a perfect blend of being "out in the country" and close enough to civilization that you don't feel isolated."
United States
Sabrina P.
The price is NZ$837
includes taxes & fees
15 Nov - 16 Nov
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill
A hot tub with a wooden deck and outdoor furniture.

16. the bourbon barrel escape HotTub Game Room pets ok

the bourbon barrel escape HotTub Game Room pets ok
Shelbyville
10.0 out of 10, Exceptional, (1 review)
"The host was super helpful and friendly! We had everything that was advertised. The House was cozy and fun for a group of friends. Wonderful stay!"
United States
Breanna N.
The price is NZ$1,104
includes taxes & fees
9 Dec - 10 Dec
the bourbon barrel escape HotTub Game Room pets ok
A kitchen with a wooden countertop, a white vase with dried flowers, and a gold decorative sign on the wall.

17. 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, (12 reviews)
"The place was perfect for the 6 of us!! Close to the distilleries as a bonus!"
United States
Erik S.
The price is NZ$498
includes taxes & fees
22 Nov - 23 Nov
Miss Reba's Love is a charming house with a warm Kentucky feel.
A covered deck with outdoor furniture, a grill, and a view of a lake and surrounding houses.

18. Bourbon Trail Lakehouse

Bourbon Trail Lakehouse
Frankfort
9.6 out of 10, Exceptional, (66 reviews)
"Great stay!"
United States
Beth S.
The price is NZ$519
includes taxes & fees
15 Dec - 16 Dec
Bourbon Trail Lakehouse
A spacious living room with a fireplace, leather furniture, and a large TV mounted on the wall.

19. 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
9.0 out of 10, Wonderful, (12 reviews)
"Excellent location and very clean property in Frankfort. We had a fantastic time during our stay and would definitely book again next time we come into town."
United States
Chris B.
The price is NZ$352
includes taxes & fees
15 Nov - 16 Nov
This gem sits in the heart of picturesque South Frankfort, near the Kentucky river
Private kitchen

20. Bourbon trail - conveniently located 8 min to buffalo trace

Bourbon trail - conveniently located 8 min to buffalo trace
Frankfort
8.8 out of 10, Excellent, (5 reviews)
"Cozy home, very inviting place. The place was well maintained and clean. "
United States
Ethiel R.
The price is NZ$686
includes taxes & fees
17 Nov - 18 Nov
Bourbon trail - conveniently located 8 min to buffalo trace
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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