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Our top choices for Simpsonville holiday rentals

1. 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 £133
includes taxes & fees
30 Aug - 31 Aug
Unique Downtown Studio with an Industrial Vibe

2. 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 £137
includes taxes & fees
30 Aug - 31 Aug
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

3. 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 £256
includes taxes & fees
30 Aug - 31 Aug
Quiet Downtown Maple Cottage Gem

4. StudioRes by Marriott Louisville East

StudioRes by Marriott Louisville East
3.0 star property
Jeffersontown
9.0 out of 10, Wonderful, (2 reviews)
"Was great enjoyed our stay and time there"
United States
Tammy
The price is £81
includes taxes & fees
1 Sept - 2 Sept
StudioRes by Marriott Louisville East

5. 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, (47 reviews)
"Great house and location. Enjoyed our stay. Would use this location again."
United States
Donald A.
The price is £169
includes taxes & fees
3 Sept - 4 Sept
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby

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 £318
includes taxes & fees
27 Aug - 28 Aug
Beautiful restored Victorian farmhouse

7. 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, (25 reviews)
"Everything was outstanding!"
United States
John W.
The price is £207
includes taxes & fees
31 Aug - 1 Sept
Historic stone cabin near Bourbon Trail on private 13 acre estate property!

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)
"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 £278
includes taxes & fees
8 Sept - 9 Sept
Near Highways and a 20 Min Drive to Louisville's Main Attractions

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

St. Matthew’s - Walk to Shops & Restaurants
St. Matthews
9.0 out of 10, Wonderful, (12 reviews)
"The neighborhood is safe and we walked around to enjoy all the nearby shops and restaurants. Very quiet and peaceful, enjoyed the porch every morning."
United States
Stacy B.
The price is £241
includes taxes & fees
30 Aug - 31 Aug
St. Matthew’s - Walk to Shops & Restaurants

10. Charming Clifton Loft with Balcony & Free

Charming Clifton Loft with Balcony & Free
Clifton
10.0 out of 10, Exceptional, (36 reviews)
"Everything was exactly as described. Location is perfect near great shops and restaurants. Will definitely use again. Owner super nice and great communicator. "
United States
Amanda H.
The price is £169
includes taxes & fees
7 Sept - 8 Sept
Charming Clifton Loft with Balcony & Free

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, (151 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 £299
includes taxes & fees
31 Aug - 1 Sept
Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

12. 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 £257
includes taxes & fees
2 Sept - 3 Sept
Charming house in one of Louisville's most coveted neighborhoods

13. Riverside Suite: Walk to Big Four Bridge &

Riverside Suite: Walk to Big Four Bridge &
Jeffersonville
9.6 out of 10, Exceptional, (44 reviews)
"Awesome little spot "
United States
Paul G.
The price is £114
includes taxes & fees
27 Aug - 28 Aug
Riverside Suite: Walk to Big Four Bridge &

14. The Bellwether Hotel

The Bellwether Hotel
3.5 star property
Tyler Park
9.0 out of 10, Wonderful, (54 reviews)
"Would stay again. Clean and comfortable in a great location. "
United States
David
The price is £125
includes taxes & fees
30 Aug - 31 Aug
The Bellwether Hotel

15. Hot Tub|Game Room|Speakeasy|FirePit|Bourbon Trail

Hot Tub|Game Room|Speakeasy|FirePit|Bourbon Trail
Shelbyville
10.0 out of 10, Exceptional, (23 reviews)
"Great location perfect house to enjoy"
United States
tim d.
The price is £416
includes taxes & fees
30 Aug - 31 Aug
Hot Tub|Game Room|Speakeasy|FirePit|Bourbon Trail

16. 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 £368
includes taxes & fees
31 Aug - 1 Sept
The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade Barn, Sleeps 12+

17. Renovated 2BR/1BA Oasis in Jeffersonville - 10 Mins to Louisville - with Yard

Renovated 2BR/1BA Oasis in Jeffersonville - 10 Mins to Louisville - with Yard
Jeffersonville
10.0 out of 10, Exceptional, (8 reviews)
"You won’t regret it! Private parking, quiet neighborhood, and fully stocked supplies for your stay! Easy check in and great hostess!"
United States
Sharonda
The price is £176
includes taxes & fees
27 Aug - 28 Aug
Renovated 2BR/1BA Oasis in Jeffersonville - 10 Mins to Louisville - with Yard

18. American Pharoah Twin Spires Suite

American Pharoah Twin Spires Suite
Jeffersonville
10.0 out of 10, Exceptional, (6 reviews)
"Great place in downtown Jeffersonville. Clean and great location for Abbey Road on the River. Just had a few suggestions for mgr, im sure he'll consider. We'd def stay here again!"
United States
doris S.
The price is £108
includes taxes & fees
30 Aug - 31 Aug
American Pharoah Twin Spires Suite

19. 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, (37 reviews)
"Great close to everything clean place definitely recommend "
United States
Jefferey S.
The price is £540
includes taxes & fees
8 Sept - 9 Sept
Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!

20. 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.
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill
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, apart-hotels, 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 £81 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?

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 10 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.