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

Simpsonville Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Simpsonville holiday rentals

1. Spacious Bourbon retreat near Downtown Louisville!

Spacious Bourbon retreat near Downtown Louisville!
Simpsonville
The price is NZ$762
includes taxes & fees
14 Oct - 15 Oct
Spacious Bourbon retreat near Downtown Louisville!

2. StudioRes by Marriott Louisville East

StudioRes by Marriott Louisville East
3.0 star property
Jeffersontown
8.0 out of 10, Very good, (11 reviews)
"The front desk staff made check in/out so smooth & were amazing!"
United States
Brandon
The price is NZ$197
includes taxes & fees
28 Oct - 29 Oct
StudioRes by Marriott Louisville East

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 NZ$316
includes taxes & fees
12 Oct - 13 Oct
Unique Downtown Studio with an Industrial Vibe

4. 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 NZ$525
includes taxes & fees
25 Oct - 26 Oct
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby

5. 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, (22 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 NZ$326
includes taxes & fees
11 Oct - 12 Oct
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

6. 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 NZ$791
includes taxes & fees
15 Oct - 16 Oct
Beautiful restored Victorian farmhouse

7. 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, (10 reviews)
"Stay was great, the place was perfect, and the view was beautiful."
United States
Bobby E.
The price is NZ$1,025
includes taxes & fees
4 Nov - 5 Nov
The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade Barn, Sleeps 12+

8. 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 NZ$1,097
includes taxes & fees
13 Oct - 14 Oct
Bourbon Trail! Game Room Hot Tub Speakeasy FirePit

9. The Bellwether Hotel

The Bellwether Hotel
3.5 star property
Tyler Park
9.0 out of 10, Wonderful, (60 reviews)
"This is a hotel not to be missed. The Art Deco style in the rooms combined with the cleanliness and boutique style makes it a Louisville treasure. Plenty of street parking and a great neighborhood."
United States
Sandy
The price is NZ$278
includes taxes & fees
26 Oct - 27 Oct
The Bellwether Hotel

10. 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)
"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 NZ$864
includes taxes & fees
12 Oct - 13 Oct
Near Highways and a 20 Min Drive to Louisville's Main Attractions

11. 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 NZ$731
includes taxes & fees
19 Oct - 20 Oct
Captain's Cabin Bed & Breakfast: Bourbon Trail. History & Romance

12. 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, (39 reviews)
"Great close to everything clean place definitely recommend "
United States
Jefferey S.
The price is NZ$1,282
includes taxes & fees
18 Oct - 19 Oct
Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!

13. Stellar Suites

Stellar Suites
4.5 star property
Downtown Louisville
9.4 out of 10, Exceptional, (155 reviews)
"Location was great near meant restaurants and nightspots"
United States
Kevin
The price is NZ$296
includes taxes & fees
18 Oct - 19 Oct
Stellar Suites

14. 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, (87 reviews)
"Enjoyed the location and quiet neighborhood. You will not be one disappointed."
United States
Tania B.
The price is NZ$693
includes taxes & fees
12 Oct - 13 Oct
Charming house in one of Louisville's most coveted neighborhoods

15. 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, (9 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$921
includes taxes & fees
11 Oct - 12 Oct
Renovated 3 bedroom, 2.5 bath 1,900 sq ft home with finished walkout basement

16. On-Site Tastings, 32 Acre Estate, Shuffleboard , 20 minutes to Buffalo Trace

On-Site Tastings, 32 Acre Estate, Shuffleboard , 20 minutes to Buffalo Trace
Waddy
9.0 out of 10, Wonderful, (7 reviews)
"Some friends and I were in town for a bourbon tour and a Keeneland visit. The property is gorgeous, and centrally located between Lexington and Louisville, The house is immaculate and perfect for a trip like this. The host is excellent, and every detail of the property was thought of. Our stay was over and above anything we imagined. Thank You!! "
United States
Timothy S.
The price is NZ$1,451
includes taxes & fees
13 Oct - 14 Oct
On-Site Tastings, 32 Acre Estate, Shuffleboard , 20 minutes to Buffalo Trace

17. #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 NZ$691
includes taxes & fees
1 Nov - 2 Nov
#18 Kentucky Sunrise - Lakefront Home with spacuios patio and Hot Tub

18. 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, (56 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.
Seabiscuit 5- Relax And Kick Back with private Hot Tub and communal Pool

19. CozySuites at Nulu

CozySuites at Nulu
4.0 star property
Downtown Louisville
7.6 out of 10, Good, (36 reviews)
"We love staying at this location when we come to Louisville. It’s a great apartment that is conveniently located. Love the view of the Big Four Bridge at night!"
United States
Jennifer
The price is NZ$383
includes taxes & fees
13 Oct - 14 Oct
CozySuites at Nulu

20. #29 Angels Envy Lakefront Home with Hot Tub and Resort Pool

#29 Angels Envy Lakefront Home with Hot Tub and Resort Pool
Taylorsville
9.2 out of 10, Wonderful, (29 reviews)
"Very clean. Nice place! Recommended"
United States
Anonymous traveller
The price is NZ$702
includes taxes & fees
3 Nov - 4 Nov
#29 Angels Envy Lakefront Home with Hot Tub and Resort Pool
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Simpsonville Hotel Reviews

Find out more about Simpsonville

Everything you need to know about Simpsonville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Simpsonville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Simpsonville holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Simpsonville holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Simpsonville. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Simpsonville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Simpsonville holiday rentals we have selected for you start as low as NZ$197 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Simpsonville rentals

At Expedia, we put the best Simpsonville holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Simpsonville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Simpsonville holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Simpsonville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Parklike Estate in the Heart of Louisville w/Pool and Gardens -- Family Friendly: This holiday home rental outside of Simpsonville offers an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Simpsonville?

Choose from 11 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.