Holiday Homes in Pleasureville

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Check prices for these dates

Our top choices for Pleasureville holiday homes

1. Haven of the Bluegrass | Bourbon Trail Getaway!

Haven of the Bluegrass | Bourbon Trail Getaway!
Shelbyville
The price is AU$636
includes taxes & fees
29 Nov - 30 Nov
Haven of the Bluegrass | Bourbon Trail Getaway!

2. The Shelby House | Historic Charm, Modern Comfort

The Shelby House | Historic Charm, Modern Comfort
Shelbyville
The price is AU$392
includes taxes & fees
15 Nov - 16 Nov
The Shelby House | Historic Charm, Modern Comfort

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 AU$555
includes taxes & fees
16 Nov - 17 Nov
Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views

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 AU$799
includes taxes & fees
17 Nov - 18 Nov
Kentucky Bourbon Trail: Hot Tub & Game Room

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 AU$481
includes taxes & fees
15 Nov - 16 Nov
Quiet Downtown Maple Cottage Gem

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 AU$385
includes taxes & fees
15 Nov - 16 Nov
Ridge View Villa #1 -Haven in the Heart of the Bourbon Trail.

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 AU$395
includes taxes & fees
15 Nov - 16 Nov
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby

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
The price is AU$881
includes taxes & fees
29 Nov - 30 Nov
Bourbon Trail | 4BR, Sleeps 10, Barrel Sauna, Hot Tub, Gym, Game Room, Fire Pits

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 AU$222
includes taxes & fees
16 Nov - 17 Nov
This house is a 2 bedroom(s), 1 bathrooms, located in Frankfort, KY.

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 AU$440
includes taxes & fees
30 Nov - 1 Dec
Beautiful New 2-Bedroom Villa with Stunning Rolling-Hill Views

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

University Stay | Sleeps 10 | Game Room + Firepit + Grill
Frankfort
The price is AU$400
includes taxes & fees
29 Nov - 30 Nov
University Stay | Sleeps 10 | Game Room + Firepit + Grill

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 AU$733
includes taxes & fees
15 Nov - 16 Nov
Renovated 3 bedroom, 2.5 bath 1,900 sq ft home with finished walkout basement

13. Spacious Bourbon retreat near Downtown Louisville!

Spacious Bourbon retreat near Downtown Louisville!
Simpsonville
The price is AU$692
includes taxes & fees
15 Nov - 16 Nov
Spacious Bourbon retreat near Downtown Louisville!

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

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 AU$687
includes taxes & fees
15 Nov - 16 Nov
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill

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 AU$898
includes taxes & fees
29 Nov - 30 Nov
the bourbon barrel escape HotTub Game Room pets ok

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 AU$414
includes taxes & fees
22 Nov - 23 Nov
Miss Reba's Love is a charming house with a warm Kentucky feel.

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 AU$390
includes taxes & fees
15 Nov - 16 Nov
Bourbon Trail Lakehouse

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 AU$291
includes taxes & fees
29 Nov - 30 Nov
This gem sits in the heart of picturesque South Frankfort, near the Kentucky river

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 AU$627
includes taxes & fees
29 Nov - 30 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.