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

Simpsonville Holiday Rentals

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Our top choices for Simpsonville holiday rentals

St. Matthew’s - Walk to Shops & Restaurants

St. Matthew’s - Walk to Shops & Restaurants
St. Matthews
9.0 out of 10, Wonderful, (12 reviews)
"We had everything we needed. Great location!"
United States
Adam S.
The price is NZ$676
includes taxes & fees
15 July - 16 July
St. Matthew’s - Walk to Shops & Restaurants

StudioRes by Marriott Louisville East

StudioRes by Marriott Louisville East
3.0 star property
Jeffersontown
The price is NZ$250
includes taxes & fees
2 Aug - 3 Aug
StudioRes by Marriott Louisville East

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, (148 reviews)
"Host were nice and friendly "
United States
Robert M.
The price is NZ$630
includes taxes & fees
12 July - 13 July
Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

The Bellwether Hotel

The Bellwether Hotel
3.5 star property
Tyler Park
9.0 out of 10, Wonderful, (51 reviews)
"Would stay again. Clean and comfortable in a great location. "
United States
David
The price is NZ$284
includes taxes & fees
3 Aug - 4 Aug
The Bellwether Hotel

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 NZ$779
includes taxes & fees
14 July - 15 July
Beautiful restored Victorian farmhouse

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, (23 reviews)
"Amazing, would stay again in a heartbeat"
United States
Ian M.
The price is NZ$285
includes taxes & fees
14 July - 15 July
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

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 NZ$626
includes taxes & fees
3 Aug - 4 Aug
Quiet Downtown Maple Cottage Gem

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 NZ$356
includes taxes & fees
3 Aug - 4 Aug
Top Floor Apt Near Churchill Downs & Expo Center

Kentucky Bourbon Trail: Hot Tub & Game Room

Kentucky Bourbon Trail: Hot Tub & Game Room
Bagdad
10.0 out of 10, Exceptional, (24 reviews)
"We enjoyed our stay. It's a great cozy and comfortable place that's secluded and private. Iris was a great host. "
United States
Madison W.
The price is NZ$991
includes taxes & fees
13 July - 14 July
Kentucky Bourbon Trail: Hot Tub & Game Room

NEW Cozy Home in Shelby Park Near Cafes & Stores

NEW Cozy Home in Shelby Park Near Cafes & Stores
Shelby Park
9.2 out of 10, Wonderful, (15 reviews)
"Perfect location and house for several people!"
United States
Pam H.
The price is NZ$706
includes taxes & fees
21 July - 22 July
NEW Cozy Home in Shelby Park Near Cafes & Stores

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 NZ$313
includes taxes & fees
13 July - 14 July
Unique Downtown Studio with an Industrial Vibe

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, (25 reviews)
"Awesome place, it was clean and spacious! "
United States
Ben M.
The price is NZ$896
includes taxes & fees
12 July - 13 July
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill

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 NZ$715
includes taxes & fees
3 Aug - 4 Aug
Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views

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, (23 reviews)
"Everything was outstanding!"
United States
John W.
The price is NZ$489
includes taxes & fees
21 July - 22 July
Historic stone cabin near Bourbon Trail on private 13 acre estate property!

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, (84 reviews)
The price is NZ$600
includes taxes & fees
20 July - 21 July
Charming house in one of Louisville's most coveted neighborhoods

Close to Everything in Louisville!!!

Close to Everything in Louisville!!!
Camp Taylor
9.4 out of 10, Exceptional, (40 reviews)
"It was a great stay"
United States
Jim M.
The price is NZ$466
includes taxes & fees
20 July - 21 July
Close to Everything in Louisville!!!

Minutes from Churchill Downs & Downtown Lou!

Minutes from Churchill Downs & Downtown Lou!
Schnitzelburg
10.0 out of 10, Exceptional, (9 reviews)
"Met my brother there for the weekend. Great food just 2 blocks away. Very happy with our stay. We would stay there again!"
United States
Greg B.
The price is NZ$627
includes taxes & fees
21 July - 22 July
Minutes from Churchill Downs & Downtown Lou!

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 NZ$323
includes taxes & fees
26 July - 27 July
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

Stunning Victorian Home - prime location minutes from Louisville

Stunning Victorian Home - prime location minutes from Louisville
Jeffersonville
9.8 out of 10, Exceptional, (29 reviews)
"We really enjoyed our stay. Close to everything!"
United States
cheryl n.
The price is NZ$994
includes taxes & fees
19 July - 20 July
Stunning Victorian Home - prime location minutes from Louisville

Spacious 3BD Luxury Stay

Spacious 3BD Luxury Stay
Louisville
8.8 out of 10, Excellent, (23 reviews)
"Very clean house. Great location for our stay. "
United States
Megan
The price is NZ$592
includes taxes & fees
22 July - 23 July
Spacious 3BD Luxury Stay
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

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$250 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?

The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville: This holiday home rental outside of Simpsonville is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books in this rental home to help you unwind.

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.