Search Vacation Homes in Simpsonville

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Simpsonville vacation homes

The Burb Inn - Nulu & Downtown *w/Firepit*

The Burb Inn - Nulu & Downtown *w/Firepit*
Phoenix Hill
9.8 out of 10, Exceptional, (6 reviews)
"The host was great. She communicated the whole stay and was very helpful. The house was smaller than anticipated and only had one very small shower."
United States
Jaime S.
The price is AED 520
AED 1,179 total
includes taxes & fees
27 May - 28 May
The Burb Inn - Nulu & Downtown *w/Firepit*

Bourbon Trail Retreat: Hot Tub & Game Room

Bourbon Trail Retreat: Hot Tub & Game Room
Bagdad
10.0 out of 10, Exceptional, (24 reviews)
"We enjoyed our stay. It's a great cozy and comfortable place that's secluded and private. Iris was a great host. "
United States
Madison W.
The price is AED 808
AED 2,259 total
includes taxes & fees
19 May - 20 May
Bourbon Trail Retreat: Hot Tub & Game Room

Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views

Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views
Waddy
9.0 out of 10, Wonderful, (11 reviews)
"Clean, quiet and a great location. "
United States
Marla B.
The price is AED 466
AED 1,306 total
includes taxes & fees
27 May - 28 May
Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views

Quiet Downtown Maple Cottage Gem

Quiet Downtown Maple Cottage Gem
Shelbyville
The price is AED 463
AED 1,289 total
includes taxes & fees
24 May - 25 May
Quiet Downtown Maple Cottage Gem

Close to Everything in Louisville!!!

Close to Everything in Louisville!!!
Camp Taylor
9.4 out of 10, Exceptional, (39 reviews)
"This is a great little place to stay! Close to the Exposition Center and a lot of other attractions. It is an older place but clean and comfortable. This is our second stay at this place. "
United States
jaggers959
The price is AED 386
AED 993 total
includes taxes & fees
19 May - 20 May
Close to Everything in Louisville!!!

Luxury 6-Bedroom Estate on 7 Private Acres with Hot Tub, Theater & Fire Pit

Luxury 6-Bedroom Estate on 7 Private Acres with Hot Tub, Theater & Fire Pit
Frankfort
10.0 out of 10, Exceptional, (6 reviews)
"Wonderful location and fantastic space for our family! "
United States
Erica R.
The price is AED 1,901
AED 3,956 total
includes taxes & fees
19 May - 20 May
Luxury 6-Bedroom Estate on 7 Private Acres with Hot Tub, Theater & Fire Pit

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, (20 reviews)
"Beautiful home and surroundings!"
United States
Peg H.
The price is AED 734
AED 1,845 total
includes taxes & fees
19 May - 20 May
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill

Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!

Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!
Shelby Park
9.6 out of 10, Exceptional, (23 reviews)
"This home is warm and cozy and close to everything we had planned."
United States
Dawn G.
The price is AED 347
AED 838 total
includes taxes & fees
19 May - 20 May
Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!

St. Matthew’s - Walk to Shops & Restaurants

St. Matthew’s - Walk to Shops & Restaurants
St. Matthews
9.0 out of 10, Wonderful, (10 reviews)
"It was everything we needed."
United States
Carmen C.
The price is AED 281
AED 1,464 total
includes taxes & fees
31 May - 1 Jun
St. Matthew’s - Walk to Shops & Restaurants

Carriage House, 7 minutes from downtown Louisville

Carriage House, 7 minutes from downtown Louisville
louisville
10.0 out of 10, Exceptional, (56 reviews)
"Amazing host! Great place to stay."
United States
Robert M.
The price is AED 496
AED 900 total
includes taxes & fees
19 May - 20 May
Carriage House, 7 minutes from downtown Louisville

+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+

+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+
Jeffersonville
9.4 out of 10, Exceptional, (90 reviews)
"Very nice place"
United States
Seth B.
The price is AED 495
AED 1,216 total
includes taxes & fees
19 May - 20 May
+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+

Cozy Kentucky Derby stay close to Churchill Downs!

Cozy Kentucky Derby stay close to Churchill Downs!
Jeffersonville
The price is AED 333
AED 918 total
includes taxes & fees
19 May - 20 May
Cozy Kentucky Derby stay close to Churchill Downs!

Perfect Kentucky Derby stay near Churchill Downs!

Perfect Kentucky Derby stay near Churchill Downs!
Jeffersonville
10.0 out of 10, Exceptional, (1 review)
"It was a great place to stay! "
United States
Lexi S.
The price is AED 333
AED 873 total
includes taxes & fees
19 May - 20 May
Perfect Kentucky Derby stay near Churchill Downs!

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, (19 reviews)
"House was cozy, and host was responsive. Rooms were clean and welcoming. A lovely place to stay."
United States
Alec S.
The price is AED 400
AED 598 total
includes taxes & fees
8 Jun - 9 Jun
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

The Adelyn, where comfort meets convenience

The Adelyn, where comfort meets convenience
Jeffersonville
10.0 out of 10, Exceptional, (8 reviews)
"The host was super responsive. The place was absolutely a gem!"
United States
Jeffery
The price is AED 453
AED 1,138 total
includes taxes & fees
19 May - 20 May
The Adelyn, where comfort meets convenience

Minutes from Churchill Downs & Downtown Lou!

Minutes from Churchill Downs & Downtown Lou!
Schnitzelburg
10.0 out of 10, Exceptional, (9 reviews)
"Met my brother there for the weekend. Great food just 2 blocks away. Very happy with our stay. We would stay there again!"
United States
Greg B.
The price is AED 661
AED 1,317 total
includes taxes & fees
21 May - 22 May
Minutes from Churchill Downs & Downtown Lou!

Whiskey Stop-Close to Ky Expo, Walkable & Parking!

Whiskey Stop-Close to Ky Expo, Walkable & Parking!
Germantown
10.0 out of 10, Exceptional, (76 reviews)
"The amenities were great and the house was the perfect spot for our weekend getaway. "
United States
Janessa D.
The price is AED 337
AED 754 total
includes taxes & fees
10 Jun - 11 Jun
Whiskey Stop-Close to Ky Expo, Walkable & Parking!

Chestnut Street Charmer-Walk to Louisville!

Chestnut Street Charmer-Walk to Louisville!
Jeffersonville
10.0 out of 10, Exceptional, (15 reviews)
"The house was clean and spacious. A great place to stay while in town for a family gathering."
United States
Connie D.
The price is AED 606
AED 1,249 total
includes taxes & fees
26 May - 27 May
Chestnut Street Charmer-Walk to Louisville!

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, (33 reviews)
"We will stay here over and over again. It’s a lovely place that a perfect location."
United States
Jennifer H.
The price is AED 182
AED 637 total
includes taxes & fees
26 May - 27 May
Stylish House Walking Distance from the Fun of the Highlands!

The Burnt Barrel | New HotTub & Grill | Backyard!

The Burnt Barrel | New HotTub & Grill | Backyard!
Germantown
10.0 out of 10, Exceptional, (4 reviews)
"This property is simply wonderful. The atmosphere is super nice and cozy, and the area is super quiet. I had an amazing night, and the weather was perfect for a dip in the hot tub . I definitely recommend it, and I am sure I will return to this beautiful property."
Mexico
Juan Miguel
The price is AED 435
AED 947 total
includes taxes & fees
19 May - 20 May
The Burnt Barrel | New HotTub & Grill | Backyard!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Simpsonville Hotel Reviews