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

Simpsonville Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Simpsonville vacation rentals

Exterior

1. StudioRes by Marriott Louisville East

StudioRes by Marriott Louisville East
3.0 star property
Jeffersontown
7.6 out of 10, Good, (4 reviews)
"Was great enjoyed our stay and time there"
United States
Tammy
$109 nightly
The price is $128
Sep 11 - Sep 12
Total with taxes and fees
StudioRes by Marriott Louisville East
Living area

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
Sep 15 - Sep 16
Total with taxes and fees
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
Bar (on property)

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.
$152 nightly
The price is $169
Sep 13 - Sep 14
Total with taxes and fees
Unique Downtown Studio with an Industrial Vibe
Outdoor spa tub

4. 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.
$526 nightly
The price is $584
Sep 13 - Sep 14
Total with taxes and fees
Bourbon Trail! Game Room Hot Tub Speakeasy FirePit
Exterior

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, (48 reviews)
"Great house and location. Enjoyed our stay. Would use this location again."
United States
Donald A.
$262 nightly
The price is $292
Sep 14 - Sep 15
Total with taxes and fees
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
Private kitchen

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.
$380 nightly
The price is $422
Sep 14 - Sep 15
Total with taxes and fees
Beautiful restored Victorian farmhouse
Living area

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.
$343 nightly
The price is $398
Oct 5 - Oct 6
Total with taxes and fees
Near Highways and a 20 Min Drive to Louisville's Main Attractions
Exterior

8. Captain's Cabin Bed & Breakfast: Louder Than Life! Bourbon Trail History Romance

Captain's Cabin Bed & Breakfast: Louder Than Life! Bourbon Trail History Romance
Louisville
9.8 out of 10, Exceptional, (152 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.
$315 nightly
The price is $365
Sep 14 - Sep 15
Total with taxes and fees
Captain's Cabin Bed & Breakfast: Louder Than Life! Bourbon Trail History Romance
Exterior

9. 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
9.8 out of 10, Exceptional, (9 reviews)
"Stay was great, the place was perfect, and the view was beautiful."
United States
Bobby E.
$390 nightly
The price is $434
Sep 13 - Sep 14
Total with taxes and fees
The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade, Pickle Ball, Sleeps 12+
Private kitchen

10. 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.
$300 nightly
The price is $348
Sep 14 - Sep 15
Total with taxes and fees
Charming house in one of Louisville's most coveted neighborhoods
Interior

11. 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, (27 reviews)
"Everything was outstanding!"
United States
John W.
$241 nightly
The price is $280
Sep 13 - Sep 14
Total with taxes and fees
Historic stone cabin near Bourbon Trail on private 13 acre estate property!
Private kitchen

12. 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
$161 nightly
The price is $172
Sep 14 - Sep 15
Total with taxes and fees
Top Floor Apt Near Churchill Downs & Expo Center
Exterior

13. Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!

Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Louisville
9.8 out of 10, Exceptional, (87 reviews)
"We had a great time! "
United States
Amber H.
$1,108 nightly
The price is $1,285
Sep 14 - Sep 15
Total with taxes and fees
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Exterior

14. Luxury lodge in the heart of the Bluegrass

Luxury lodge in the heart of the Bluegrass
Waddy
10.0 out of 10, Exceptional, (9 reviews)
"Great property, nice location, well appointed. It is close to the interstate and with the leaves off, truck traffic could be heard from the top floor master bed. We would stay here again."
United States
Anonymous traveler
$1,419 nightly
The price is $1,580
Sep 11 - Sep 12
Total with taxes and fees
Luxury lodge in the heart of the Bluegrass
Exterior

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

St. Matthew’s - Walk to Shops & Restaurants
St. Matthews
9.0 out of 10, Wonderful, (12 reviews)
"cute housegreat location easy peasy"
United States
Lisa M.
$297 nightly
The price is $345
Oct 5 - Oct 6
Total with taxes and fees
St. Matthew’s - Walk to Shops & Restaurants
Private kitchen

16. Cozy stay in Germantown near Downtown attractions!

Cozy stay in Germantown near Downtown attractions!
Germantown
10.0 out of 10, Exceptional, (25 reviews)
"Nice rooms! Good location!"
United States
Ashton Y.
$188 nightly
The price is $200
Sep 13 - Sep 14
Total with taxes and fees
Cozy stay in Germantown near Downtown attractions!
Private kitchen

17. Modern unit near Churchill Downs and Expo Center!

Modern unit near Churchill Downs and Expo Center!
Audubon
10.0 out of 10, Exceptional, (4 reviews)
"Loved it. And would love to stay again"
United States
Emily V.
$171 nightly
The price is $184
Oct 6 - Oct 7
Total with taxes and fees
Modern unit near Churchill Downs and Expo Center!
Private kitchen

18. Charming Clifton Loft with Balcony & Free

Charming Clifton Loft with Balcony & Free
Clifton
10.0 out of 10, Exceptional, (37 reviews)
"Great location in Clifton neighborhood!"
United States
Kelly D.
$194 nightly
The price is $209
Sep 13 - Sep 14
Total with taxes and fees
Charming Clifton Loft with Balcony & Free
Interior

19. Riverside Suite: Walk to Big Four Bridge &

Riverside Suite: Walk to Big Four Bridge &
Jeffersonville
9.6 out of 10, Exceptional, (44 reviews)
"Easy check in and check out. Nice stay. "
United States
Kelsey R.
$167 nightly
The price is $178
Sep 13 - Sep 14
Total with taxes and fees
Riverside Suite: Walk to Big Four Bridge &
Room

20. Cozy studio near music hall, food stops and shops!

Cozy studio near music hall, food stops and shops!
Germantown
10.0 out of 10, Exceptional, (85 reviews)
"We really enjoyed our stay here. The place was clean and comfortable. "
Canada
Jonathon B.
$161 nightly
The price is $173
Sep 13 - Sep 14
Total with taxes and fees
Cozy studio near music hall, food stops and shops!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Simpsonville Hotel Reviews

Drury Inn & Suites Louisville North

Drury Inn & Suites Louisville North

10/10 Excellent
"Quick overnight stay but the room was clean and the property looked nice. We plan to come back for a longer stay at some point so I’ll have more to say."
Victor 1-night trip
Posted less than an hour ago
Drury Inn & Suites Louisville North

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 $128 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?

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

How many vacation rentals are there in Simpsonville?

Choose from 10 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.