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
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Simpsonville vacation rentals

Bar (on property)

Unique Downtown Studio with an Industrial Vibe

Unique Downtown Studio with an Industrial Vibe
Shelbyville
10.0 out of 10, Exceptional, (32 reviews)
"The VRBO was perfect. Has the elegant modern feel just like the pictures show and has lots of space to hang out and relax. Loved the location and how walkable it was to coffee shops, restaurants, and bars. Loved staying here and highly recommend!"
United States
Lucas L.
The price is ￥14,551
￥28,724 total
includes taxes & fees
Jul 14 - Jul 15
Unique Downtown Studio with an Industrial Vibe
Interior

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, (23 reviews)
"Everything was outstanding!"
United States
John W.
The price is ￥28,811
￥45,264 total
includes taxes & fees
Jul 21 - Jul 22
Historic stone cabin near Bourbon Trail on private 13 acre estate property!
Fridge, microwave, oven, stovetop

Quiet Downtown Maple Cottage Gem

Quiet Downtown Maple Cottage Gem
Shelbyville
10.0 out of 10, Exceptional, (1 review)
"Very convenient for Horse Show we were attending. Everything was as described and the hosts were very accommodating. "
United States
Marlena J.
The price is ￥20,372
￥56,731 total
includes taxes & fees
Jul 19 - Jul 20
Quiet Downtown Maple Cottage Gem
Exterior

St. Matthew’s - Walk to Shops & Restaurants

St. Matthew’s - Walk to Shops & Restaurants
St. Matthews
9.0 out of 10, Wonderful, (12 reviews)
"The neighborhood is safe and we walked around to enjoy all the nearby shops and restaurants. Very quiet and peaceful, enjoyed the porch every morning."
United States
Stacy B.
The price is ￥11,641
￥63,243 total
includes taxes & fees
Jul 14 - Jul 15
St. Matthew’s - Walk to Shops & Restaurants
Fridge, microwave, oven, stovetop

Beautiful restored Victorian farmhouse

Beautiful restored Victorian farmhouse
Shelbyville
9.4 out of 10, Exceptional, (14 reviews)
"Great location to downtown Shelbyville. Porch is awesome!!"
United States
Alison L.
The price is ￥35,650
￥72,072 total
includes taxes & fees
Jul 20 - Jul 21
Beautiful restored Victorian farmhouse
Fridge, microwave, oven, stovetop

Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill

Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill
Frankfort
9.8 out of 10, Exceptional, (25 reviews)
"Awesome place, it was clean and spacious! "
United States
Ben M.
The price is ￥32,304
￥82,852 total
includes taxes & fees
Jul 26 - Jul 27
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill
TV

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.
The price is ￥15,360
￥29,622 total
includes taxes & fees
Jul 19 - Jul 20
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
Exterior

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, (149 reviews)
"Host were nice and friendly "
United States
Robert M.
The price is ￥37,106
￥59,584 total
includes taxes & fees
Jul 15 - Jul 16
Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance
Smart TV, books

Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee!

Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee!
Clifton
10.0 out of 10, Exceptional, (35 reviews)
"Quirky, clean, comfortable, and spacious!"
United States
D K.
The price is ￥9,216
￥28,524 total
includes taxes & fees
Jul 15 - Jul 16
Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee!
Fridge, microwave, oven, stovetop

Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Charlestown
10.0 out of 10, Exceptional, (23 reviews)
"Amazing, would stay again in a heartbeat"
United States
Ian M.
The price is ￥17,138
￥25,760 total
includes taxes & fees
Jul 14 - Jul 15
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Living area

Cozy Cottage House in Louisville

Cozy Cottage House in Louisville
Schnitzelburg
9.0 out of 10, Wonderful, (8 reviews)
The price is ￥12,490
￥29,177 total
includes taxes & fees
Jul 21 - Jul 22
Cozy Cottage House in Louisville
Smart TV

Close to Everything in Louisville!!!

Close to Everything in Louisville!!!
Camp Taylor
9.4 out of 10, Exceptional, (40 reviews)
"It was a great stay"
United States
Jim M.
The price is ￥16,976
￥43,726 total
includes taxes & fees
Jul 20 - Jul 21
Close to Everything in Louisville!!!
Smart TV, books

Renovated 2BR/1BA Oasis in Jeffersonville - 10 Mins to Louisville - with Yard

Renovated 2BR/1BA Oasis in Jeffersonville - 10 Mins to Louisville - with Yard
Jeffersonville
10.0 out of 10, Exceptional, (6 reviews)
"Our stay was great. Beautiful house , very accommodating, everything we needed! Comfy and cozy and close to Big four bridge, would highly recommend "
United States
Sam T.
The price is ￥14,697
￥35,242 total
includes taxes & fees
Jul 21 - Jul 22
Renovated 2BR/1BA Oasis in Jeffersonville - 10 Mins to Louisville - with Yard
Fridge, microwave, oven, stovetop

KING Sleep8 4Bed 2BR 2 BA Swepson Hideaway 202

KING Sleep8 4Bed 2BR 2 BA Swepson Hideaway 202
Shelby Park
10.0 out of 10, Exceptional, (4 reviews)
"Easy check in and clean!"
United States
Sally W.
The price is ￥11,479
￥46,714 total
includes taxes & fees
Jul 21 - Jul 22
KING Sleep8 4Bed 2BR 2 BA Swepson Hideaway 202
Terrace/patio

Kentucky Bourbon Trail: Hot Tub & Game Room

Kentucky Bourbon Trail: Hot Tub & Game Room
Bagdad
10.0 out of 10, Exceptional, (24 reviews)
"Great place with a grill and hot tub. Lots of parking space. "
United States
Samantha M.
The price is ￥37,833
￥91,860 total
includes taxes & fees
Jul 14 - Jul 15
Kentucky Bourbon Trail: Hot Tub & Game Room
Exterior

Luxury farmhouse on Bourbon Trail with hot tub - Bulleit 4 mi - Frankfort 15 mi

Luxury farmhouse on Bourbon Trail with hot tub - Bulleit 4 mi - Frankfort 15 mi
Bagdad
10.0 out of 10, Exceptional, (16 reviews)
"Great location and very clean. Plenty of room to spread out and relax. Carrie is a Professional and thoughtful host!!"
United States
David S.
The price is ￥62,861
￥126,288 total
includes taxes & fees
Jul 15 - Jul 16
Luxury farmhouse on Bourbon Trail with hot tub - Bulleit 4 mi - Frankfort 15 mi
Property grounds

Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill

Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill
Crescent Hill
10.0 out of 10, Exceptional, (130 reviews)
"The place was clean and had all the basic needs in the kitchen. Great location to all different parts of Louisville.We would stay here again."
United States
Jodi D.
The price is ￥21,018
￥37,909 total
includes taxes & fees
Jul 14 - Jul 15
Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill
Smart TV, books

Cozy Riverside Apt. Min to Downtown Louisville. King Bed, Coffee Bar!

Cozy Riverside Apt. Min to Downtown Louisville. King Bed, Coffee Bar!
Jeffersonville
9.6 out of 10, Exceptional, (42 reviews)
"Easy check in and check out. Nice stay. "
United States
Kelsey R.
The price is ￥12,934
￥27,404 total
includes taxes & fees
Jul 17 - Jul 18
Cozy Riverside Apt. Min to Downtown Louisville. King Bed, Coffee Bar!
Property amenity

StudioRes by Marriott Louisville East

StudioRes by Marriott Louisville East
3.0 star property
Jeffersontown
The price is ￥18,771
￥23,036 total
includes taxes & fees
Aug 2 - Aug 3
StudioRes by Marriott Louisville East
Fridge, microwave, oven, stovetop

Preston Retreat - Convenient Germantown Location

Preston Retreat - Convenient Germantown Location
Merriwether
8.2 out of 10, Very Good, (13 reviews)
"Close to where we needed to be"
United States
terry k.
The price is ￥10,509
￥35,223 total
includes taxes & fees
Aug 3 - Aug 4
Preston Retreat - Convenient Germantown Location
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

Studio 6 Suites Louisville, KY – Airport/Expo Center

Studio 6 Suites Louisville, KY – Airport/Expo Center

8/10 Good
"When you arrive the facility is avg to below avg. it’s a motel set up. Doors to rooms are outside. Room was clean, AC blew cold, beds comfortable lots of hot water. Extra small bathroom. No hair dryer. Affordable place to stay close to fairgrounds"
Jammi 3-night trip
Posted 2 hours ago
Studio 6 Suites Louisville, KY – Airport/Expo Center

Find out more about Simpsonville

Search for holiday rentals in Simpsonville on Expedia! You can easily find your home rentals, villas, holiday apartments in Simpsonville using one of the methods below:

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Look no further and take a look at our great range of rental properties in 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?

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 9 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.