A brick clock tower with two clocks, surrounded by dense foliage.

Simpsonville Holiday Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Simpsonville holiday rentals

Coffee/tea maker, fridge, microwave, oven

1. 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, (26 reviews)
"Awesome place, it was clean and spacious! "
United States
Ben M.
The price is HK$1,313
HK$3,659 total
includes taxes & fees
19 Aug - 20 Aug
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill
Exterior

2. 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$3,049
HK$6,126 total
includes taxes & fees
19 Aug - 20 Aug
Luxury farmhouse on Bourbon Trail with hot tub - Bulleit 4 mi - Frankfort 15 mi
Exterior

3. Luxury lodge in the heart of the Bluegrass

Luxury lodge in the heart of the Bluegrass
Waddy
10.0 out of 10, Exceptional, (9 reviews)
"Great property, nice location, well appointed. It is close to the interstate and with the leaves off, truck traffic could be heard from the top floor master bed. We would stay here again."
United States
Anonymous traveller
The price is HK$10,446
HK$16,489 total
includes taxes & fees
18 Aug - 19 Aug
Luxury lodge in the heart of the Bluegrass
Interior

4. Bourbon Trail Getaway ~ Hot Tub + Dogs Welcome + Game Room + Cornhole + KY Fun

Bourbon Trail Getaway ~ Hot Tub + Dogs Welcome + Game Room + Cornhole + KY Fun
Shelbyville
9.8 out of 10, Exceptional, (26 reviews)
"Great location for the derby only 30 min easy drive to Church hills downs. Place was very clean and easy checkin"
United States
kerrie D.
The price is HK$1,999
HK$4,294 total
includes taxes & fees
31 Aug - 1 Sept
Bourbon Trail Getaway ~ Hot Tub + Dogs Welcome + Game Room + Cornhole + KY Fun
Coffee/tea maker, fridge, microwave, oven

5. Hilltop Retreat-Bourbon Trail-Pool w/Slide-Hot Tub

Hilltop Retreat-Bourbon Trail-Pool w/Slide-Hot Tub
Bloomfield
10.0 out of 10, Exceptional, (10 reviews)
"Nice newly updated home. Enjoyed stay."
United States
Jonathan H.
Hilltop Retreat-Bourbon Trail-Pool w/Slide-Hot Tub
Exterior

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, (8 reviews)
"Stay was great, the place was perfect, and the view was beautiful."
United States
Bobby E.
The price is HK$2,929
HK$3,732 total
includes taxes & fees
10 Aug - 11 Aug
The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade Barn, Sleeps 12+
Coffee/tea maker, fridge, microwave, oven

7. Beautiful restored Victorian farmhouse

Beautiful restored Victorian farmhouse
Shelbyville
9.4 out of 10, Exceptional, (14 reviews)
"Great location to downtown Shelbyville. Porch is awesome!!"
United States
Alison L.
The price is HK$1,730
HK$3,496 total
includes taxes & fees
10 Aug - 11 Aug
Beautiful restored Victorian farmhouse
TV

8. 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, (20 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
16 Aug - 17 Aug
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
Bar (on property)

9. Unique Downtown Studio with an Industrial Vibe

Unique Downtown Studio with an Industrial Vibe
Shelbyville
10.0 out of 10, Exceptional, (32 reviews)
"The VRBO was perfect. Has the elegant modern feel just like the pictures show and has lots of space to hang out and relax. Loved the location and how walkable it was to coffee shops, restaurants, and bars. Loved staying here and highly recommend!"
United States
Lucas L.
The price is HK$706
HK$1,393 total
includes taxes & fees
11 Aug - 12 Aug
Unique Downtown Studio with an Industrial Vibe
Outdoor spa tub

10. Game Room Hot Tub Speakeasy FirePit Bourbon Trail

Game Room Hot Tub Speakeasy FirePit Bourbon Trail
Shelbyville
10.0 out of 10, Exceptional, (22 reviews)
"Great location perfect house to enjoy"
United States
tim d.
The price is HK$3,558
HK$4,325 total
includes taxes & fees
10 Aug - 11 Aug
Game Room Hot Tub Speakeasy FirePit Bourbon Trail
Coffee/tea maker, fridge, microwave, oven

11. 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 HK$988
HK$2,752 total
includes taxes & fees
10 Aug - 11 Aug
Quiet Downtown Maple Cottage Gem
Outdoor dining

12. Distiller's Dream - Bourbon Trail Country Fun - 12 minutes to Bardstown Square

Distiller's Dream - Bourbon Trail Country Fun - 12 minutes to Bardstown Square
Coxs Creek
9.8 out of 10, Exceptional, (20 reviews)
"Great place to stay! House was just as listed. Plenty of space and the Bar-n was a great place to hangout."
United States
Nicholas H.
The price is HK$2,118
HK$5,585 total
includes taxes & fees
10 Aug - 11 Aug
Distiller's Dream - Bourbon Trail Country Fun - 12 minutes to Bardstown Square
Dining

13. 3.7 Acre Estate w/ Heated Pool, 5 Kings-2 Game Rms

3.7 Acre Estate w/ Heated Pool, 5 Kings-2 Game Rms
La Grange
10.0 out of 10, Exceptional, (25 reviews)
"We had the best experience staying here. From the gorgeous property, fabulous pool, to the excellent communication from the host. 10/10 definitely would recommend and would stay there again. We did not want to leave! "
United States
Kelly B.
The price is HK$4,676
HK$10,475 total
includes taxes & fees
1 Sept - 2 Sept
3.7 Acre Estate w/ Heated Pool, 5 Kings-2 Game Rms
Smart TV, fireplace, printers

14. 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, (57 reviews)
"Ross was super helpful from start to finish, and had plenty of space for our 14 guests to stay. This property would be very very high on my list to stay at again as a home base for a future Kentucky Derby weekend, or even a bourbon trail trip."
United States
Stephen Y.
The price is HK$1,235
HK$2,918 total
includes taxes & fees
10 Aug - 11 Aug
Near Highways and a 20 Min Drive to Louisville's Main Attractions
Dining

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

Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!
Jeffersontown
9.4 out of 10, Exceptional, (36 reviews)
"Great close to everything clean place definitely recommend "
United States
Jefferey S.
The price is HK$2,816
HK$5,818 total
includes taxes & fees
9 Aug - 10 Aug
Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!
Coffee/tea maker, fridge, microwave, oven

16. 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, (85 reviews)
"Home was great for a short stay. Kitchen fully furnished and all niceties such as coffee, snacks and toiletries. "
United States
Tony A.
The price is HK$1,482
HK$2,694 total
includes taxes & fees
31 Aug - 1 Sept
Charming house in one of Louisville's most coveted neighborhoods
Interior

17. Historic stone cabin near Bourbon Trail on private 13 acre estate property!

Historic stone cabin near Bourbon Trail on private 13 acre estate property!
Louisville
10.0 out of 10, Exceptional, (24 reviews)
"Everything was outstanding!"
United States
John W.
The price is HK$1,398
HK$2,196 total
includes taxes & fees
9 Aug - 10 Aug
Historic stone cabin near Bourbon Trail on private 13 acre estate property!
Exterior

18. 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, (86 reviews)
"We had a great time! "
United States
Amber H.
The price is HK$4,341
HK$8,872 total
includes taxes & fees
10 Aug - 11 Aug
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Exterior

19. Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance
Louisville
9.8 out of 10, Exceptional, (150 reviews)
"Host were nice and friendly "
United States
Robert M.
The price is HK$2,000
HK$3,150 total
includes taxes & fees
1 Sept - 2 Sept
Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance
Property grounds

20. Charlie Long Cabin - Active Heroes

Charlie Long Cabin - Active Heroes
Bullitt County
10.0 out of 10, Exceptional, (1 review)
"Peaceful, beautifully maintained property"
United States
renee b.
The price is HK$1,961
HK$2,231 total
includes taxes & fees
7 Aug - 8 Aug
Charlie Long Cabin - Active Heroes
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 East

Drury Inn & Suites Louisville East

10/10 Excellent
"Hotel is well maintained with a great breakfast as well."
Mason 1-night trip
Posted 1 hour ago
Drury Inn & Suites Louisville East

Find out more about Simpsonville

Search for holiday rentals in Simpsonville on Expedia! You can easily find your home rentals, villas, holiday apartments in Simpsonville using one of the methods below:

  • View our selection of featured holiday rentals in Simpsonville
  • Use the map to find apartments and other holiday homes in the Simpsonville neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Simpsonville while they last

Look no further and take a look at our great range of rental properties in Simpsonville!

Frequently asked questions

Can I find a holiday rental in Simpsonville?

Yes, there are holiday rentals close to the most popular sights in Simpsonville, 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 Simpsonville has to offer?

Riverfront Home on the Ohio River, Private Dock, Hot Tub, Sleeps 8: This holiday home rental outside of Simpsonville is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with 1 hot tub and a selection of books.

How many holiday rentals are there in Simpsonville?

Choose from 9 Expedia holiday rentals in Simpsonville for a memorable holiday.

What’s there to see and do in Simpsonville?

While exploring the area, visit family-friendly sights like IceLand Sports Complex, or get outside and enjoy nature at Beckley Creek Park. The Outlet Shoppes of the Bluegrass and Whitney M. Young, Jr. Birthplace are other places to visit while you're in town.

What’s a holiday rental in Simpsonville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Simpsonville. Holiday rentals offer extras like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for family trips or small group gatherings.