Simpsonville Vacation Rentals

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Check prices for these dates

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

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
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, (608 reviews)
"Only stayed overnight. Guy at the front desk was nice. Only had a few issues but they were handled quickly."
United States
Kristin
The price is AED 235
AED 277 total
includes taxes & fees
22 Nov - 23 Nov
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
The price is AED 327
AED 407 total
includes taxes & fees
21 Nov - 22 Nov
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.
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.
The price is AED 331
AED 620 total
includes taxes & fees
18 Nov - 19 Nov
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.
The price is AED 610
AED 1,112 total
includes taxes & fees
10 Dec - 11 Dec
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.
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.
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.
The price is AED 655
AED 981 total
includes taxes & fees
15 Nov - 16 Nov
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
The price is AED 261
AED 516 total
includes taxes & fees
16 Nov - 17 Nov
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)
"Location was great. Close to highway access, food and entertainment. Enjoyed it thoroughly. Thank you for being flexible at check in."
United States
John B.
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.
The price is AED 977
AED 1,462 total
includes taxes & fees
14 Dec - 15 Dec
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, (267 reviews)
"Perfect location and room was great!"
United States
Gary
The price is AED 241
AED 621 total
includes taxes & fees
19 Nov - 20 Nov
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.
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.
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, (69 reviews)
"All was great, clean and comfortable. Only issue is parking, but this was mentioned in description, so was expecting it."
United States
Paul
The price is AED 497
AED 601 total
includes taxes & fees
29 Nov - 30 Nov
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.
The price is AED 198
AED 492 total
includes taxes & fees
18 Nov - 19 Nov
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.
The price is AED 253
AED 680 total
includes taxes & fees
15 Nov - 16 Nov
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.
The price is AED 724
AED 1,366 total
includes taxes & fees
29 Nov - 30 Nov
#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
The price is AED 400
AED 657 total
includes taxes & fees
19 Nov - 20 Nov
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

A swimming pool with clear water, surrounded by blue walls and a seating area with chairs and a table.
Hampton Inn Simpsonville

Hampton Inn Simpsonville

Hampton Inn Simpsonville
Simpsonville

10/10 Excellent

Great experience and wonderful breakfast
United States
Alison
Reviewed October 22, 2024
Hampton Inn Simpsonville

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.