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
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Simpsonville vacation rentals

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 AED 235
AED 797 total
includes taxes & fees
28 Jun - 29 Jun
Preston Retreat - Convenient Germantown Location
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 AED 770
AED 1,589 total
includes taxes & fees
29 Jun - 30 Jun
Beautiful restored Victorian farmhouse
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.
Quiet Downtown Maple Cottage Gem
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 AED 331
AED 653 total
includes taxes & fees
28 Jun - 29 Jun
Unique Downtown Studio with an Industrial Vibe
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)
"Our stay was very pleasant, great location, lots of great restaurants. Tyler the host was was always available when we had an issue. "
United States
Max D.
The price is AED 275
AED 725 total
includes taxes & fees
28 Jun - 29 Jun
Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee!
Iron/ironing board, WiFi, bed sheets

Alfesco - Walkable Highlands Guesthouse

Alfesco - Walkable Highlands Guesthouse
Deer Park
8.8 out of 10, Excellent, (12 reviews)
"Great communication, accommodations, and location- Trifecta! "
United States
Lisa K.
The price is AED 213
AED 543 total
includes taxes & fees
22 Jul - 23 Jul
Alfesco - Walkable Highlands Guesthouse
Outdoor dining

Mid-Century Modern Gem Pet-Friendly 2BR w/ Deck

Mid-Century Modern Gem Pet-Friendly 2BR w/ Deck
Schnitzelburg
9.2 out of 10, Wonderful, (5 reviews)
"Nice place! "
United States
Sierra S.
The price is AED 392
AED 997 total
includes taxes & fees
21 Jul - 22 Jul
Mid-Century Modern Gem Pet-Friendly 2BR w/ Deck
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)
"We had everything we needed. Great location!"
United States
Adam S.
The price is AED 298
AED 1,479 total
includes taxes & fees
30 Jun - 1 Jul
St. Matthew’s - Walk to Shops & Restaurants
Front of property

The Bellwether Hotel

The Bellwether Hotel
3.5 star property
Tyler Park
9.0 out of 10, Wonderful, (51 reviews)
"Would stay again. Clean and comfortable in a great location. "
United States
David
The price is AED 487
AED 566 total
includes taxes & fees
1 Jul - 2 Jul
The Bellwether Hotel
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, (23 reviews)
"Awesome place, it was clean and spacious! "
United States
Ben M.
The price is AED 734
AED 1,891 total
includes taxes & fees
28 Jun - 29 Jun
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 AED 430
AED 763 total
includes taxes & fees
20 Jul - 21 Jul
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
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 AED 261
AED 1,061 total
includes taxes & fees
29 Jun - 30 Jun
KING Sleep8 4Bed 2BR 2 BA Swepson Hideaway 202
Living area

Stylish House Walking Distance from the Fun of the Highlands!

Stylish House Walking Distance from the Fun of the Highlands!
Phoenix Hill
9.4 out of 10, Exceptional, (35 reviews)
"Solid place, close to everything, perfect for Bourbon Trail trip!"
United States
Jake F.
The price is AED 496
AED 1,036 total
includes taxes & fees
27 Jul - 28 Jul
Stylish House Walking Distance from the Fun of the Highlands!
Smart TV

Close to Everything in Louisville!!!

Close to Everything in Louisville!!!
Camp Taylor
9.4 out of 10, Exceptional, (40 reviews)
"Everything about our stay was excellent."
United States
James H.
The price is AED 386
AED 989 total
includes taxes & fees
29 Jun - 30 Jun
Close to Everything in Louisville!!!
2 bedrooms, desk, iron/ironing board, travel crib

Historic Highlands Retreat! Spacious Rustic Apt in the Heart of it all!

Historic Highlands Retreat! Spacious Rustic Apt in the Heart of it all!
Cherokee Triangle
9.0 out of 10, Wonderful, (6 reviews)
The price is AED 275
AED 661 total
includes taxes & fees
28 Jun - 29 Jun
Historic Highlands Retreat! Spacious Rustic Apt in the Heart of it all!
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, (148 reviews)
"Host were nice and friendly "
United States
Robert M.
The price is AED 843
AED 1,349 total
includes taxes & fees
28 Jun - 29 Jun
Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance
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, (21 reviews)
"Everything was outstanding!"
United States
John W.
The price is AED 655
AED 1,028 total
includes taxes & fees
28 Jun - 29 Jun
Historic stone cabin near Bourbon Trail on private 13 acre estate property!
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)
"This little apartment was great for what we needed! Clean, efficient, fast communication with the host, and right on the river near cute shops and restaurants. The washer/dryer was a great bonus. "
United States
Courtney
The price is AED 257
AED 581 total
includes taxes & fees
28 Jun - 29 Jun
Cozy Riverside Apt. Min to Downtown Louisville. King Bed, Coffee Bar!
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)
"Clean and was as advertised Great location for our plans "
United States
Mike A.
The price is AED 389
AED 585 total
includes taxes & fees
29 Jun - 30 Jun
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
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

Hawthorn Suites by Wyndham Louisville East

Hawthorn Suites by Wyndham Louisville East

10/10 Excellent
"As usual this was a good experience and the best value in the area. Staff was good, rooms were clean and breakfast was adequate."
Brett 1-night trip
Posted 3 hours ago
Hawthorn Suites by Wyndham Louisville East

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.