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

Simpsonville Vacation Rentals

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Our top choices for Simpsonville vacation 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.
$160 nightly
The price is $178
Aug 16 - Aug 17
Total with taxes and fees
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.
$165 nightly
The price is $183
Aug 16 - Aug 17
Total with taxes and fees
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.
$316 nightly
The price is $351
Aug 23 - Aug 24
Total with taxes and fees
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
$108 nightly
The price is $127
Aug 20 - Aug 21
Total with taxes and fees
StudioRes by Marriott Louisville East

5. Beautiful restored Victorian farmhouse

Beautiful restored Victorian farmhouse
Shelbyville
9.2 out of 10, Wonderful, (15 reviews)
"Great location to downtown Shelbyville. Porch is awesome!!"
United States
Alison L.
$401 nightly
The price is $446
Aug 17 - Aug 18
Total with taxes and fees
Beautiful restored Victorian farmhouse

6. 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.
$244 nightly
The price is $283
Aug 18 - Aug 19
Total with taxes and fees
Historic stone cabin near Bourbon Trail on private 13 acre estate property!

7. 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.
$360 nightly
The price is $418
Sep 7 - Sep 8
Total with taxes and fees
Near Highways and a 20 Min Drive to Louisville's Main Attractions

8. Boulevard Stays Expansive 1BR Suite, Parking

Boulevard Stays Expansive 1BR Suite, Parking
Middletown
8.8 out of 10, Excellent, (10 reviews)
"Enjoyed the stay, clean, great Location!!!Will stay again…"
United States
Stephanie W.
$185 nightly
The price is $214
Aug 17 - Aug 18
Total with taxes and fees
Boulevard Stays Expansive 1BR Suite, Parking

9. 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.
$301 nightly
The price is $349
Aug 17 - Aug 18
Total with taxes and fees
Charming house in one of Louisville's most coveted neighborhoods

10. 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)
"Host were nice and friendly "
United States
Robert M.
$349 nightly
The price is $405
Aug 16 - Aug 17
Total with taxes and fees
Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

11. 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.
$283 nightly
The price is $328
Aug 18 - Aug 19
Total with taxes and fees
St. Matthew’s - Walk to Shops & Restaurants

12. 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.
$506 nightly
The price is $561
Aug 23 - Aug 24
Total with taxes and fees
Game Room Hot Tub Speakeasy FirePit Bourbon Trail

13. 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.
$639 nightly
The price is $742
Aug 16 - Aug 17
Total with taxes and fees
Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!

14. Cozy Cottage House in Louisville

Cozy Cottage House in Louisville
Schnitzelburg
9.2 out of 10, Wonderful, (9 reviews)
"It's cute and perfect for a weekend stay."
United States
Krista R.
$179 nightly
The price is $207
Aug 16 - Aug 17
Total with taxes and fees
Cozy Cottage House in Louisville

15. The Bellwether Hotel

The Bellwether Hotel
3.5 star property
Tyler Park
9.0 out of 10, Wonderful, (52 reviews)
"Would stay again. Clean and comfortable in a great location. "
United States
David
$132 nightly
The price is $152
Aug 16 - Aug 17
Total with taxes and fees
The Bellwether Hotel

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

The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade,Pickle 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.
$442 nightly
The price is $492
Aug 18 - Aug 19
Total with taxes and fees
The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade,Pickle Barn, Sleeps 12+

17. OPEN 4BR/2BA • Sleeps 8 • Near Hwy • Covered Deck • Close to Downtown & Expo Ctr

OPEN 4BR/2BA • Sleeps 8 • Near Hwy • Covered Deck • Close to Downtown & Expo Ctr
Hikes Point
10.0 out of 10, Exceptional, (67 reviews)
"Nice property close to attractions."
United States
Glenn C.
$397 nightly
The price is $460
Aug 17 - Aug 18
Total with taxes and fees
OPEN 4BR/2BA • Sleeps 8 • Near Hwy • Covered Deck • Close to Downtown & Expo Ctr

18. 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.
$158 nightly
The price is $173
Aug 17 - Aug 18
Total with taxes and fees
Charming Clifton Loft with Balcony & Free

19. KING Sleep8 4Bed 2BR 2 BA Swepson Hideaway 202

KING Sleep8 4Bed 2BR 2 BA Swepson Hideaway 202
Shelby Park
10.0 out of 10, Exceptional, (4 reviews)
"Easy check in and clean!"
United States
Sally W.
$194 nightly
The price is $224
Aug 17 - Aug 18
Total with taxes and fees
KING Sleep8 4Bed 2BR 2 BA Swepson Hideaway 202

20. 2BR Home Near Zoo & Fairgrounds – Family-Friendly!

2BR Home Near Zoo & Fairgrounds – Family-Friendly!
Poplar Level
8.0 out of 10, Very Good, (3 reviews)
"Great location and perfect size for us! Would stay again."
United States
CA S.
$236 nightly
The price is $273
Aug 16 - Aug 17
Total with taxes and fees
2BR Home Near Zoo & Fairgrounds – Family-Friendly!
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Simpsonville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Simpsonville vacation 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 low season months. For more hustle and bustle, you may prefer to visit Simpsonville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $127 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Simpsonville rentals

At Expedia, we put the best Simpsonville vacation 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 vacation.

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 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?

Riverfront Home on the Ohio River, Private Dock, Hot Tub, Sleeps 8: This vacation home rental outside of Simpsonville is located on a lake and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a hot tub and a selection of books.

How many vacation rentals are there in Simpsonville?

Choose from 9 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.