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Simpsonville Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Simpsonville vacation rentals

TV

1. 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 ￥14,815
￥28,571 total
includes taxes & fees
Sep 29 - Sep 30
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
Exterior

2. StudioRes by Marriott Louisville East

StudioRes by Marriott Louisville East
3.0 star property
Jeffersontown
8.0 out of 10, Very good, (5 reviews)
"This is about the best place that you can spend your dollar and get the professionalism that you deserve"
United States
James
The price is ￥16,702
￥20,569 total
includes taxes & fees
Sep 29 - Sep 30
StudioRes by Marriott Louisville East
Bar (on property)

3. Unique Downtown Studio with an Industrial Vibe

Unique Downtown Studio with an Industrial Vibe
Shelbyville
10.0 out of 10, Exceptional, (32 reviews)
"Wonderful location in a very nice small town. Grocery store, coffee shop and many other amenities close by.The property was very spacious and well done for 2 people."
United States
Kathleen S.
The price is ￥14,747
￥28,568 total
includes taxes & fees
Oct 5 - Oct 6
Unique Downtown Studio with an Industrial Vibe
Outdoor spa tub

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.
The price is ￥75,792
￥95,585 total
includes taxes & fees
Sep 22 - Sep 23
Bourbon Trail! Game Room Hot Tub Speakeasy FirePit
Coffee/tea maker, fridge, microwave, oven

5. Beautiful restored Victorian farmhouse

Beautiful restored Victorian farmhouse
Shelbyville
9.2 out of 10, Wonderful, (15 reviews)
"Lovely place, great outdoor seating areas, and spacious rooms."
United States
Joann E.
The price is ￥34,387
￥66,394 total
includes taxes & fees
Sep 24 - Sep 25
Beautiful restored Victorian farmhouse
Exterior

6. 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 ￥26,042
￥49,938 total
includes taxes & fees
Oct 11 - Oct 12
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
Interior

7. Riverside Suite: Walk to Big Four Bridge &

Riverside Suite: Walk to Big Four Bridge &
Jeffersonville
9.6 out of 10, Exceptional, (44 reviews)
"Easy check in and check out. Nice stay. "
United States
Kelsey R.
The price is ￥8,472
￥23,931 total
includes taxes & fees
Sep 28 - Sep 29
Riverside Suite: Walk to Big Four Bridge &
Smart TV, fireplace, printers

8. 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)
"Great place!"
United States
Nakoma F.
The price is ￥27,454
￥62,093 total
includes taxes & fees
Oct 5 - Oct 6
Near Highways and a 20 Min Drive to Louisville's Main Attractions
Exterior

9. 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 traveler
The price is ￥207,725
￥327,010 total
includes taxes & fees
Oct 2 - Oct 3
Luxury lodge in the heart of the Bluegrass
Coffee/tea maker, fridge, microwave, oven

10. 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, (86 reviews)
"Enjoyed the location and quiet neighborhood. You will not be one disappointed."
United States
Tania B.
The price is ￥29,631
￥53,399 total
includes taxes & fees
Oct 14 - Oct 15
Charming house in one of Louisville's most coveted neighborhoods
2 bedrooms, travel crib, WiFi (free), bed sheets

11. Rooftop Patio & Games in Historic Highlands

Rooftop Patio & Games in Historic Highlands
Cherokee Triangle
9.2 out of 10, Wonderful, (14 reviews)
"Great pace to stay if you want to be in the middle of a vibrant night life. Tons of restaurants and bars. Only a short uber ride to downtown. The host was great and responded quickly with any questions."
United States
Nan W.
The price is ￥7,798
￥26,707 total
includes taxes & fees
Oct 1 - Oct 2
Rooftop Patio & Games in Historic Highlands
Exterior

12. The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade, Pickle Ball, Sleeps 12+

The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade, Pickle Ball, Sleeps 12+
Shelbyville
9.8 out of 10, Exceptional, (10 reviews)
"Stay was great, the place was perfect, and the view was beautiful."
United States
Bobby E.
The price is ￥85,773
￥109,178 total
includes taxes & fees
Sep 29 - Sep 30
The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade, Pickle Ball, Sleeps 12+
Exterior

13. 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, (153 reviews)
"One of the most beautiful locations I've had the pleasure of staying in. Plan to book again in the future. So much historical value and comfort"
United States
Bill H.
The price is ￥39,767
￥61,184 total
includes taxes & fees
Sep 28 - Sep 29
Captain's Cabin Bed & Breakfast: Bourbon Trail. History & Romance
Interior

14. 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, (27 reviews)
"Exceptional property and experience! Don and Ron were great hosts. Will definitely stay again if we are back in the Louisville area. Highly recommend!"
United States
George S.
The price is ￥27,956
￥43,920 total
includes taxes & fees
Sep 27 - Sep 28
Historic stone cabin near Bourbon Trail on private 13 acre estate property!
Coffee/tea maker, fridge, microwave, oven

15. Top Floor Apt Near Churchill Downs & Expo Center

Top Floor Apt Near Churchill Downs & Expo Center
Audubon
10.0 out of 10, Exceptional, (4 reviews)
"Super unique spot with great ambiance and energy! You can tell the hosts put a lot of time into making it a one-of-a-kind retreat. "
United States
andrew
The price is ￥8,472
￥25,773 total
includes taxes & fees
Oct 6 - Oct 7
Top Floor Apt Near Churchill Downs & Expo Center
Front of property

16. The Bellwether Hotel

The Bellwether Hotel
3.5 star property
Tyler Park
9.0 out of 10, Wonderful, (58 reviews)
"Check in was easy, very clean and nice. Very unique property!"
United States
Amy
The price is ￥22,797
￥27,601 total
includes taxes & fees
Sep 22 - Sep 23
The Bellwether Hotel
Exterior

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

St. Matthew’s - Walk to Shops & Restaurants
St. Matthews
9.0 out of 10, Wonderful, (12 reviews)
"cute housegreat location easy peasy"
United States
Lisa M.
The price is ￥13,335
￥51,714 total
includes taxes & fees
Oct 4 - Oct 5
St. Matthew’s - Walk to Shops & Restaurants
Terrace/patio

18. Kentucky Bourbon Trail: Hot Tub & Game Room

Kentucky Bourbon Trail: Hot Tub & Game Room
Bagdad
10.0 out of 10, Exceptional, (26 reviews)
"Great place with a grill and hot tub. Lots of parking space. "
United States
Samantha M.
The price is ￥38,917
￥102,047 total
includes taxes & fees
Sep 20 - Sep 21
Kentucky Bourbon Trail: Hot Tub & Game Room
Coffee/tea maker, fridge, microwave, oven

19. Charming Clifton Loft with Balcony & Free

Charming Clifton Loft with Balcony & Free
Clifton
10.0 out of 10, Exceptional, (37 reviews)
"Great location in Clifton neighborhood!"
United States
Kelly D.
The price is ￥10,137
￥28,519 total
includes taxes & fees
Oct 4 - Oct 5
Charming Clifton Loft with Balcony & Free
Interior

20. Highlands Escape: King Bed, Coffee Bar, BBQ & WiFi

Highlands Escape: King Bed, Coffee Bar, BBQ & WiFi
Phoenix Hill
9.4 out of 10, Exceptional, (39 reviews)
"Very clean and exactly what we thought we were booking! Will book again in the future if the need arises!"
United States
Brittany H.
The price is ￥10,982
￥29,599 total
includes taxes & fees
Oct 4 - Oct 5
Highlands Escape: King Bed, Coffee Bar, BBQ & WiFi
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

Aloft by Marriott Louisville East

Aloft by Marriott Louisville East

10/10 Excellent
"Friendly staff and clean rooms, walking distance to food. It was nice after a long drive to get out and stretch legs."
Benjamin 1-night trip
Posted less than an hour ago
Aloft by Marriott 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 vacation rental in Simpsonville?

Yes, you can find vacation rentals near the most popular local attractions in Simpsonville, or you can go with a secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals in Simpsonville?

Parklike Estate in the Heart of Louisville w/Pool and Gardens -- Family Friendly: This vacation home rental outside of Simpsonville offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Simpsonville?

Choose from 10 Expedia vacation rentals in Simpsonville for a memorable vacation.

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 vacation rental in Simpsonville like?

A vacation rental is a private property you can book for a few weeks or just a few days in Simpsonville. Vacation rentals feature extras such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a family trip.