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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Simpsonville vacation homes

A kitchen counter with a vase of flowers, a coffee maker, and a small appliance.

1. Spacious Bourbon retreat near Downtown Louisville!

Spacious Bourbon retreat near Downtown Louisville!
Simpsonville
Spacious Bourbon retreat near Downtown Louisville!
A two-story house with a porch, a small garden, and a sign that reads "Hotel."

2. 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 AED 558
AED 1,108 total
includes taxes & fees
2 Nov - 3 Nov
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
A living room with a fireplace, a sofa, a coffee table, and a dining area with a table and chairs.

3. Near Highways and a 20 Min Drive to Louisville's Main Attractions

Near Highways and a 20 Min Drive to Louisville's Main Attractions
Louisville
10.0 out of 10, Exceptional, (58 reviews)
"This is the second time we’ve stayed a long weekend here and plan to do so again in the future! Highly recommended!"
United States
Clint S.
The price is AED 661
AED 1,514 total
includes taxes & fees
28 Oct - 29 Oct
Near Highways and a 20 Min Drive to Louisville's Main Attractions
A hot tub with a glass of red wine, surrounded by a lush green outdoor setting.

4. 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.
Bourbon Trail! Game Room Hot Tub Speakeasy FirePit
A modern kitchen with wooden cabinets, a marble countertop, and a dining area with a round table and chairs.

5. Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!

Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!
Jeffersontown
9.2 out of 10, Wonderful, (40 reviews)
"Great close to everything clean place definitely recommend "
United States
Jefferey S.
The price is AED 1,319
AED 2,725 total
includes taxes & fees
24 Oct - 25 Oct
Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!
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 AED 666
AED 2,828 total
includes taxes & fees
2 Nov - 3 Nov
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 modern kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a marble countertop.

7. 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 AED 298
AED 1,159 total
includes taxes & fees
26 Oct - 27 Oct
Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views
A modern kitchen with a large window, a dining area with a table and chairs, and a view of the outdoors.

8. Charming house in one of Louisville's most coveted neighborhoods

Charming house in one of Louisville's most coveted neighborhoods
Louisville
10.0 out of 10, Exceptional, (88 reviews)
"Enjoyed the location and quiet neighborhood. You will not be one disappointed."
United States
Tania B.
The price is AED 837
AED 1,471 total
includes taxes & fees
2 Nov - 3 Nov
Charming house in one of Louisville's most coveted neighborhoods
A modern kitchen with a central island, stainless steel appliances, and a large window providing natural light.

9. 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 AED 437
AED 1,018 total
includes taxes & fees
26 Oct - 27 Oct
Ridge View Villa #1 -Haven in the Heart of the Bourbon Trail.
A living room with a fireplace, a television, a sofa, and a dining area with chairs and a table.

10. #29 Angels Envy Lakefront Home with Hot Tub and Resort Pool

#29 Angels Envy Lakefront Home with Hot Tub and Resort Pool
Taylorsville
9.0 out of 10, Wonderful, (30 reviews)
"Owner was so easy to work with and very responsive! House was clean and great location! Lots of family memories made!"
United States
Kathleen Y.
The price is AED 569
AED 1,265 total
includes taxes & fees
15 Nov - 16 Nov
#29 Angels Envy Lakefront Home with Hot Tub and Resort Pool
A modern kitchen with stainless steel appliances, a built-in oven, and a microwave.

11. 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, (10 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.
Renovated 3 bedroom, 2.5 bath 1,900 sq ft home with finished walkout basement
A large rectangular swimming pool with a deck, surrounded by a white fence. There are lounge chairs and a small patio area with tables and chairs.

12. #18 Kentucky Sunrise - Lakefront Home with spacuios patio and Hot Tub

#18 Kentucky Sunrise - Lakefront Home with spacuios patio and Hot Tub
Taylorsville
9.8 out of 10, Exceptional, (56 reviews)
"Excellent view and cozy home"
United States
Adam D.
The price is AED 724
AED 1,382 total
includes taxes & fees
2 Nov - 3 Nov
#18 Kentucky Sunrise - Lakefront Home with spacuios patio and Hot Tub
A hot tub with a floating platform, surrounded by a deck with chairs and string lights.

13. Seabiscuit 5- Relax And Kick Back with private Hot Tub and communal Pool

Seabiscuit 5- Relax And Kick Back with private Hot Tub and communal Pool
Taylorsville
9.6 out of 10, Exceptional, (57 reviews)
"We thoroughly enjoyed our stay. The house was the perfect size for our group, the hot tub was great after a long day, and the game was an added bonus!"
United States
Lisa L.
The price is AED 646
AED 1,132 total
includes taxes & fees
3 Nov - 4 Nov
Seabiscuit 5- Relax And Kick Back with private Hot Tub and communal Pool
A wooden cabin with a green roof, surrounded by lush greenery and a gravel path.

14. Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!

Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Louisville
9.8 out of 10, Exceptional, (87 reviews)
"We had a great time! "
United States
Amber H.
The price is AED 2,479
AED 4,745 total
includes taxes & fees
2 Nov - 3 Nov
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
A modern kitchen with white cabinets, a dining table set for four, and a black patterned curtain.

15. 3-BDR King Suite in Mount Washington Fenced yard minutes from Louisville

3-BDR King Suite in Mount Washington Fenced yard minutes from Louisville
Mount Washington
10.0 out of 10, Exceptional, (1 review)
"We had a great experience with the host and the property. We would rent this again."
United States
Meghan T.
The price is AED 532
AED 899 total
includes taxes & fees
25 Oct - 26 Oct
3-BDR King Suite in Mount Washington Fenced yard minutes from Louisville
A wooden deck with a green door, wicker chairs, and a small table.

16. The Sweet Retreat Wheelchair Accessible Historic Home

The Sweet Retreat Wheelchair Accessible Historic Home
La Grange
10.0 out of 10, Exceptional, (7 reviews)
"We had a family gathering over Thanksgiving and the large table was very nice and appreciated. Host was very prompt with communication and most everything we needed was there. Would stay again!"
United States
Shelley S.
The price is AED 988
AED 1,708 total
includes taxes & fees
1 Nov - 2 Nov
The Sweet Retreat Wheelchair Accessible Historic Home
A spacious kitchen with a large island, wooden cabinets, and a high ceiling with exposed beams.

17. Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Charlestown
10.0 out of 10, Exceptional, (27 reviews)
"The carriage house was very roomy and nice. We would definitely stay here again."
United States
Pam
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
A bedroom with a bed, nightstands, a ceiling fan, and a window with shutters.

18. Convenient & Cozy! Close to everything Louisville!

Convenient & Cozy! Close to everything Louisville!
Belknap
The price is AED 464
AED 1,004 total
includes taxes & fees
9 Nov - 10 Nov
Convenient & Cozy! Close to everything Louisville!
A two-story house with a front porch, a chimney, and a number '3935' on the door.

19. St. Matthew’s - Walk to Shops & Restaurants

St. Matthew’s - Walk to Shops & Restaurants
St. Matthews
9.0 out of 10, Wonderful, (15 reviews)
"cute housegreat location easy peasy"
United States
Lisa M.
The price is AED 327
AED 1,288 total
includes taxes & fees
1 Nov - 2 Nov
St. Matthew’s - Walk to Shops & Restaurants
A backyard with a barbecue grill, outdoor seating, and a fire pit.

20. Stable #3 ~ Mini Golf, Foosball, BBQ, Fire Pits

Stable #3 ~ Mini Golf, Foosball, BBQ, Fire Pits
Irish Hill
10.0 out of 10, Exceptional, (11 reviews)
"Very nice place, great location for us."
United States
peter m.
The price is AED 125
AED 714 total
includes taxes & fees
26 Oct - 27 Oct
Stable #3 ~ Mini Golf, Foosball, BBQ, Fire Pits
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 Simpsonville Hotel Reviews

Drury Inn & Suites Louisville North

Drury Inn & Suites Louisville North

8/10 Good
"The receptionist was wonderful! The hotel very clean and of course the food was great!!! There were two things that were challenging: The sheets were rough and had an odd odor ~ not pleasant at all The fan would not stay on at night as it was set. We would hear it get silent and then it would kick on. We had it set to be on all of the time with the cool temp set. So, there you have it."
Shawn 1-night trip
Posted 3 hours ago
Drury Inn & Suites Louisville North

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