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Simpsonville Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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
$480 nightly
The price is $553
Nov 3 - Nov 4
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, (606 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, (15 reviews)
"The front desk staff made check in/out so smooth & were amazing!"
United States
Brandon
$94 nightly
The price is $111
Nov 9 - Nov 10
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 4 - Nov 5
Total with taxes and fees
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
A two-story house with a porch, a small garden, and a sign that reads "Hotel."

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, (50 reviews)
"Great house and location. Enjoyed our stay. Would use this location again."
United States
Donald A.
$201 nightly
The price is $224
Nov 3 - Nov 4
Total with taxes and fees
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
A room with a leather sofa, two armchairs, a bed, and a small table with a tray.

6. Unique Downtown Studio with an Industrial Vibe

Unique Downtown Studio with an Industrial Vibe
Shelbyville
10.0 out of 10, Exceptional, (33 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.
$146 nightly
The price is $162
Nov 8 - Nov 9
Total with taxes and fees
Unique Downtown Studio with an Industrial Vibe
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 3 - Nov 4
Total with taxes and fees
Beautiful restored Victorian farmhouse
A living room with a fireplace, a sofa, a coffee table, and a dining area with a table and chairs.

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, (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.
$459 nightly
The price is $532
Nov 4 - Nov 5
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."

9. The Bellwether Hotel

The Bellwether Hotel
3.5 star property
Tyler Park
9.0 out of 10, Wonderful, (66 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
$133 nightly
The price is $153
Nov 8 - Nov 9
Total with taxes and fees
The Bellwether Hotel
A modern kitchen with wooden cabinets, a marble countertop, and a dining area with a round table and chairs.

10. 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.
$607 nightly
The price is $705
Nov 3 - Nov 4
Total with taxes and fees
Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!
A two-story house with a front porch, columns, and a well-maintained lawn.

11. 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.
$493 nightly
The price is $547
Nov 15 - Nov 16
Total with taxes and fees
Bourbon Trail! Game Room Hot Tub Speakeasy FirePit
A log cabin with a covered porch, large windows, and a well-maintained front yard.

12. 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.
$494 nightly
The price is $549
Nov 4 - Nov 5
Total with taxes and fees
The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade, Pickle Ball, Sleeps 12+
A rustic cabin with a stone chimney, wooden porch, and a garden with flowers and a wooden fence.

13. 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.
$343 nightly
The price is $398
Nov 3 - Nov 4
Total with taxes and fees
Captain's Cabin Bed & Breakfast: Bourbon Trail. History & Romance
A rustic room with stone walls, a fireplace, leather armchairs, and a wooden ceiling.

14. 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.
$232 nightly
The price is $270
Nov 8 - Nov 9
Total with taxes and fees
Historic stone cabin near Bourbon Trail on private 13 acre estate property!
A modern building with a sign reading "Stellar Suites" and a crescent moon logo.

15. 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
$162 nightly
The price is $188
Dec 2 - Dec 3
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.

16. 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, (88 reviews)
"Enjoyed the location and quiet neighborhood. You will not be one disappointed."
United States
Tania B.
$384 nightly
The price is $446
Nov 4 - Nov 5
Total with taxes and fees
Charming house in one of Louisville's most coveted neighborhoods
A hot tub with a waterfall feature, surrounded by trees and a wooden fence.

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.
$317 nightly
The price is $349
Nov 3 - Nov 4
Total with taxes and fees
#18 Kentucky Sunrise - Lakefront Home with spacuios patio and Hot Tub
A living room with a fireplace, a television, a sofa, and a dining area with chairs and a table.

18. #29 Angels Envy Lakefront Home with Hot Tub and Resort Pool

#29 Angels Envy Lakefront Home with Hot Tub and Resort Pool
Taylorsville
9.0 out of 10, Wonderful, (30 reviews)
"Owner was so easy to work with and very responsive! House was clean and great location! Lots of family memories made!"
United States
Kathleen Y.
$296 nightly
The price is $326
Nov 15 - Nov 16
Total with taxes and fees
#29 Angels Envy Lakefront Home with Hot Tub and Resort 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
$194 nightly
The price is $225
Nov 4 - Nov 5
Total with taxes and fees
CozySuites at Nulu
A woman in a striped jacket and yellow skirt walking through a hallway with a door and a light fixture.

20. 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
$139 nightly
The price is $161
Nov 4 - Nov 5
Total with taxes and fees
Hancock House
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

Fairfield Inn & Suites by Marriott Louisville Downtown

Fairfield Inn & Suites by Marriott Louisville Downtown

8/10 Good
"The room that we had the noise outside was ridiculous"
Dottie 1-night trip
Posted 1 hour ago
Fairfield Inn & Suites by Marriott 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.