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

Simpsonville Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Simpsonville vacation rentals

A dining area with a marble table and blue upholstered chairs, a kitchen with modern appliances, and a view of the outdoors through large windows.

1. Spacious Bourbon retreat near Downtown Louisville!

Spacious Bourbon retreat near Downtown Louisville!
Simpsonville
$377 nightly
The price is $403
Oct 14 - Oct 15
Total with taxes and fees
Spacious Bourbon retreat near Downtown Louisville!
A multi-story hotel with a flat facade, a parking lot in front, and a sign indicating 'STUDIOS.'

2. StudioRes by Marriott Louisville East

StudioRes by Marriott Louisville East
3.0 star property
Jeffersontown
7.6 out of 10, Good, (12 reviews)
"The front desk staff made check in/out so smooth & were amazing!"
United States
Brandon
$94 nightly
The price is $111
Oct 25 - Oct 26
Total with taxes and fees
StudioRes by Marriott Louisville East
A bar area with stools, a counter, and a television mounted on the wall.

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.
$160 nightly
The price is $178
Oct 12 - Oct 13
Total with taxes and fees
Unique Downtown Studio with an Industrial Vibe
A two-story house with a porch, a small garden, and a sign that reads "Hotel."

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.
$257 nightly
The price is $286
Oct 11 - Oct 12
Total with taxes and fees
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
A kitchen with a gas stove, a stainless steel range hood, and built-in ovens.

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.
$165 nightly
The price is $183
Nov 2 - Nov 3
Total with taxes and fees
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
A kitchen with grey cabinets, a large island, pendant lighting, and a view of the outdoors.

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.
$401 nightly
The price is $446
Oct 12 - Oct 13
Total with taxes and fees
Beautiful restored Victorian farmhouse
A log cabin with a covered porch, large windows, and a well-maintained front yard.

7. 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
10.0 out of 10, Exceptional, (11 reviews)
"Stay was great, the place was perfect, and the view was beautiful."
United States
Bobby E.
$543 nightly
The price is $604
Oct 26 - Oct 27
Total with taxes and fees
The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade, Pickle Ball, Sleeps 12+
A hot tub with a glass of red wine, surrounded by a lush green outdoor setting.

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.
$551 nightly
The price is $612
Oct 13 - Oct 14
Total with taxes and fees
Bourbon Trail! Game Room Hot Tub Speakeasy FirePit
A brick building with arched windows and a sign reading "The Bellwether."

9. The Bellwether Hotel

The Bellwether Hotel
3.5 star property
Tyler Park
9.2 out of 10, Wonderful, (62 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
$123 nightly
The price is $142
Oct 26 - Oct 27
Total with taxes and fees
The Bellwether Hotel
A living room with a fireplace, a sofa, a coffee table, and a dining area with a table and chairs.

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.
$406 nightly
The price is $471
Oct 25 - Oct 26
Total with taxes and fees
Near Highways and a 20 Min Drive to Louisville's Main Attractions
A cozy log cabin interior with a stone fireplace, leather furniture, and rustic decor.

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, (154 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.
$355 nightly
The price is $412
Oct 19 - Oct 20
Total with taxes and fees
Captain's Cabin Bed & Breakfast: Bourbon Trail. History & Romance
A modern kitchen with wooden cabinets, a marble countertop, and a dining area with a round table and chairs.

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.
$639 nightly
The price is $742
Oct 18 - Oct 19
Total with taxes and fees
Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!
A modern hotel lobby with a reception desk, seating area, and a staircase leading to the upper floor.

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
$160 nightly
The price is $186
Oct 25 - Oct 26
Total with taxes and fees
Stellar Suites
A modern kitchen with a large window, a dining area with a table and chairs, and a view of the outdoors.

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.
$347 nightly
The price is $403
Oct 12 - Oct 13
Total with taxes and fees
Charming house in one of Louisville's most coveted neighborhoods
A modern kitchen with stainless steel appliances, a built-in oven, and a microwave.

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.
$466 nightly
The price is $527
Oct 11 - Oct 12
Total with taxes and fees
Renovated 3 bedroom, 2.5 bath 1,900 sq ft home with finished walkout basement
A wooden deck with rocking chairs and a bench, surrounded by trees with autumn foliage.

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.
$680 nightly
The price is $757
Oct 14 - Oct 15
Total with taxes and fees
On-Site Tastings, 32 Acre Estate, Shuffleboard , 20 minutes to Buffalo Trace
A large rectangular swimming pool with a deck, surrounded by a white fence. There are lounge chairs and a small patio area with tables and chairs.

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.
$344 nightly
The price is $378
Nov 1 - Nov 2
Total with taxes and fees
#18 Kentucky Sunrise - Lakefront Home with spacuios patio and Hot Tub
A hot tub with a floating platform, surrounded by a deck with chairs and string lights.

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.
$280 nightly
The price is $308
Nov 1 - Nov 2
Total with taxes and fees
Seabiscuit 5- Relax And Kick Back with private Hot Tub and communal Pool
A rooftop pool area with multiple lounge chairs and umbrellas, surrounded by a high-rise building with balconies.

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
$185 nightly
The price is $215
Oct 13 - Oct 14
Total with taxes and fees
CozySuites at Nulu
A marina with boats docked, a covered seating area, and a building with a distinctive sun emblem.

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 traveler
$302 nightly
The price is $332
Nov 1 - Nov 2
Total with taxes and fees
#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.
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Top Simpsonville Hotel Reviews

Wingate by Wyndham Louisville Fair and Expo

Wingate by Wyndham Louisville Fair and Expo

10/10 Excellent
"Staff was amazing breakfast was very limited parking was great but seemed insecure"
Gabriel 1-night trip
Posted 9 hours ago
Wingate by Wyndham Louisville Fair and Expo

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 $111 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?

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 11 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.