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
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Simpsonville vacation rentals

A modern kitchen with a stainless steel sink, a built-in faucet, and a window overlooking a deck with outdoor seating.

1. Spacious Bourbon retreat near Downtown Louisville!

Spacious Bourbon retreat near Downtown Louisville!
Simpsonville
$469 nightly
The price is $521
Nov 15 - Nov 16
Total with taxes and fees
Spacious Bourbon retreat near Downtown Louisville!
A multi-story hotel with a brick facade, multiple windows, and a parking lot with several cars.

2. WoodSpring Suites Louisville Jeffersontown

WoodSpring Suites Louisville Jeffersontown
2.5 star property
Jeffersontown
7.0 out of 10, Good, (607 reviews)
"Only stayed overnight. Guy at the front desk was nice. Only had a few issues but they were handled quickly."
United States
Kristin
$64 nightly
The price is $75
Nov 22 - Nov 23
Total with taxes and fees
WoodSpring Suites Louisville Jeffersontown
A multi-story building with a 'STUDIORES' sign, featuring a modern facade with evenly spaced windows and a flat roof.

3. StudioRes by Marriott Louisville East

StudioRes by Marriott Louisville East
3.0 star property
Jeffersontown
7.6 out of 10, Good, (18 reviews)
"Clean hotel, very helpful staff."
United States
Christopher
$94 nightly
The price is $111
Nov 18 - Nov 19
Total with taxes and fees
StudioRes by Marriott Louisville East
A kitchen with a gas stove, a coffee maker, and built-in ovens.

4. 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.
$158 nightly
The price is $175
Nov 30 - Dec 1
Total with taxes and fees
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
A bar area with stools, a coffee machine, and a large metal horseshoe decoration on the wall.

5. Unique Downtown Studio with an Industrial Vibe

Unique Downtown Studio with an Industrial Vibe
Shelbyville
10.0 out of 10, Exceptional, (34 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.
$152 nightly
The price is $169
Dec 8 - Dec 9
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."

6. 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, (51 reviews)
"Great house and location. Enjoyed our stay. Would use this location again."
United States
Donald A.
$251 nightly
The price is $279
Nov 15 - Nov 16
Total with taxes and fees
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
A kitchen with grey cabinets, a large island, pendant lighting, and a view of the outdoors.

7. Beautiful restored Victorian farmhouse

Beautiful restored Victorian farmhouse
Shelbyville
9.4 out of 10, Exceptional, (16 reviews)
"Lovely place, great outdoor seating areas, and spacious rooms."
United States
Joann E.
$381 nightly
The price is $424
Nov 16 - Nov 17
Total with taxes and fees
Beautiful restored Victorian farmhouse
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, (25 reviews)
"Great location perfect house to enjoy"
United States
tim d.
$560 nightly
The price is $622
Nov 15 - Nov 16
Total with taxes and fees
Bourbon Trail! Game Room Hot Tub Speakeasy FirePit
A rustic room with stone walls, a fireplace, leather armchairs, and a wooden ceiling.

9. 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, (29 reviews)
"Beautiful cabin with beautiful views!"
United States
Frida G.
$230 nightly
The price is $267
Nov 15 - Nov 16
Total with taxes and fees
Historic stone cabin near Bourbon Trail on private 13 acre estate property!
A modern living room with a sofa, a coffee table, and a TV mounted on the wall.

10. The Duke Hotel

The Duke Hotel
2.0 star property
Downtown Louisville
8.0 out of 10, Very good, (30 reviews)
"Really nice clean place to stay for very reasonable price"
United States
Joseph
$121 nightly
The price is $140
Nov 17 - Nov 18
Total with taxes and fees
The Duke Hotel
A modern kitchen with wooden cabinets, a marble countertop, and a dining area with a round table and chairs.

11. 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, (40 reviews)
"Great close to everything clean place definitely recommend "
United States
Jefferey S.
$587 nightly
The price is $681
Nov 13 - Nov 14
Total with taxes and fees
Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!
A rustic cabin with a stone chimney, wooden porch, and a garden with flowers and a wooden fence.

12. 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, (159 reviews)
"Unique cabin in the woods. Tammy and Jan were attentive hosts. Breakfast in the morning was delicious. Would definitely stay here again"
United States
Suzanne H.
$342 nightly
The price is $397
Nov 15 - Nov 16
Total with taxes and fees
Captain's Cabin Bed & Breakfast: Bourbon Trail. History & Romance
A kitchen with white cabinets, a stainless steel refrigerator, a coffee maker, and a sink.

13. Hancock House

Hancock House
3.0 star property
Downtown Louisville
8.2 out of 10, Very good, (266 reviews)
"Perfect location and room was great!"
United States
Gary
$146 nightly
The price is $169
Nov 19 - Nov 20
Total with taxes and fees
Hancock House
A log cabin with a covered porch, large windows, and a well-maintained front yard.

14. 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, (12 reviews)
"Stay was great, the place was perfect, and the view was beautiful."
United States
Bobby E.
$581 nightly
The price is $647
Nov 30 - Dec 1
Total with taxes and fees
The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade, Pickle Ball, Sleeps 12+
A living room with a fireplace, a sofa, a coffee table, and a dining area with a table and chairs.

15. 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, (60 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.
$471 nightly
The price is $547
Nov 29 - Nov 30
Total with taxes and fees
Near Highways and a 20 Min Drive to Louisville's Main Attractions
A brick building with arched windows and a sign reading "The Bellwether."

16. The Bellwether Hotel

The Bellwether Hotel
3.5 star property
Tyler Park
9.0 out of 10, Wonderful, (68 reviews)
"All was great, clean and comfortable. Only issue is parking, but this was mentioned in description, so was expecting it."
United States
Paul
$138 nightly
The price is $159
Nov 29 - Nov 30
Total with taxes and fees
The Bellwether Hotel
A bedroom with a four-poster bed, a desk with chairs, and a sofa.

17. Alfesco - Walkable Highlands Guesthouse

Alfesco - Walkable Highlands Guesthouse
Deer Park
8.8 out of 10, Excellent, (15 reviews)
"Great communication, accommodations, and location- Trifecta! "
United States
Lisa K.
$116 nightly
The price is $134
Nov 18 - Nov 19
Total with taxes and fees
Alfesco - Walkable Highlands Guesthouse
Living area

18. Charming Clifton Loft with Balcony & Free

Charming Clifton Loft with Balcony & Free
Clifton
10.0 out of 10, Exceptional, (39 reviews)
"Great location in Clifton neighborhood!"
United States
Kelly D.
$173 nightly
The price is $186
Nov 16 - Nov 17
Total with taxes and fees
Charming Clifton Loft with Balcony & Free
A hot tub with a waterfall feature, surrounded by trees and a wooden fence.

19. #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.
$338 nightly
The price is $372
Nov 29 - Nov 30
Total with taxes and fees
#18 Kentucky Sunrise - Lakefront Home with spacuios patio and Hot Tub
A modern hotel lobby with a reception desk, seating area, and a staircase leading to the upper floor.

20. Stellar Suites

Stellar Suites
4.5 star property
Downtown Louisville
9.4 out of 10, Exceptional, (158 reviews)
"Location was great near meant restaurants and nightspots"
United States
Kevin
$157 nightly
The price is $182
Dec 13 - Dec 14
Total with taxes and fees
Stellar Suites
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

Moxy Louisville Downtown

Moxy Louisville Downtown

10/10 Excellent
"Amazing staff and location!!"
Priscilla 1-night trip
Posted 5 hours ago
Moxy Louisville Downtown

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 $75 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.