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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sep - 13 Sep

Our top choices for Simpsonville vacation homes

Property grounds

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 1,924
AED 3,994 total
includes taxes & fees
20 May - 21 May
Luxury 6-Bedroom Estate on 7 Private Acres with Hot Tub, Theater & Fire Pit
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, (20 reviews)
"Beautiful home and surroundings!"
United States
Peg H.
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill
Terrace/patio

Bourbon Trail Retreat: Hot Tub & Game Room

Bourbon Trail Retreat: Hot Tub & Game Room
Bagdad
10.0 out of 10, Exceptional, (24 reviews)
The price is AED 808
AED 2,259 total
includes taxes & fees
20 May - 21 May
Bourbon Trail Retreat: 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 AED 1,428
AED 2,869 total
includes taxes & fees
2 Jun - 3 Jun
Luxury farmhouse on Bourbon Trail with hot tub - Bulleit 4 mi - Frankfort 15 mi
TV, offices

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 403
AED 1,226 total
includes taxes & fees
2 Jun - 3 Jun
Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views
Smart TV

Private A-frame Cabin - Hot tub, Firepit & Views

Private A-frame Cabin - Hot tub, Firepit & Views
Waddy
10.0 out of 10, Exceptional, (3 reviews)
"Loved our stay, very clean in a peaceful country setting. Communication with owner was great and very accommodating!!"
United States
Dana C.
The price is AED 1,060
AED 1,981 total
includes taxes & fees
2 Jun - 3 Jun
Private A-frame Cabin - Hot tub, Firepit & Views
Interior

Bourbon Trail Getaway ~ Hot Tub + Dogs Welcome + Game Room + Cornhole + KY Fun

Bourbon Trail Getaway ~ Hot Tub + Dogs Welcome + Game Room + Cornhole + KY Fun
Shelbyville
9.8 out of 10, Exceptional, (21 reviews)
"Great house for my family of five! The pool/ping pong table was the perfect way to spend our wit we getaway. "
United States
Jenn S.
The price is AED 812
AED 1,852 total
includes taxes & fees
20 May - 21 May
Bourbon Trail Getaway ~ Hot Tub + Dogs Welcome + Game Room + Cornhole + KY Fun
Fridge, microwave, oven, stovetop

Hilltop Retreat-Bourbon Trail-Pool w/Slide-Hot Tub

Hilltop Retreat-Bourbon Trail-Pool w/Slide-Hot Tub
Bloomfield
10.0 out of 10, Exceptional, (4 reviews)
Hilltop Retreat-Bourbon Trail-Pool w/Slide-Hot Tub
Outdoor spa tub

Hot Tub•Sleeps 10•Firepit•Gameroom•Bourbon Trail

Hot Tub•Sleeps 10•Firepit•Gameroom•Bourbon Trail
Shelbyville
10.0 out of 10, Exceptional, (20 reviews)
"Overall great value and accommodations. Would highly recommend this property."
United States
Chad K.
The price is AED 1,527
AED 1,941 total
includes taxes & fees
8 Jun - 9 Jun
Hot Tub•Sleeps 10•Firepit•Gameroom•Bourbon Trail
Fridge, microwave, oven, stovetop

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
Terrace/patio

Pendleton, KY Farm in Oldham Co

Pendleton, KY Farm in Oldham Co
Pendleton
10.0 out of 10, Exceptional, (4 reviews)
"The house was perfect for our group of 8. Very clean, great gathering space inside and out and well maintained. Highly recommended! Thanks Betty!"
United States
Scott B.
The price is AED 1,650
AED 3,422 total
includes taxes & fees
29 May - 30 May
Pendleton, KY Farm in Oldham Co
Exterior detail

The Sweet Retreat Wheelchair Accessible Historic Home

The Sweet Retreat Wheelchair Accessible Historic Home
La Grange
10.0 out of 10, Exceptional, (5 reviews)
"We had a family gathering over Thanksgiving and the large table was very nice and appreciated. Host was very prompt with communication and most everything we needed was there. Would stay again!"
United States
Shelley S.
The price is AED 988
AED 1,708 total
includes taxes & fees
24 May - 25 May
The Sweet Retreat Wheelchair Accessible Historic Home
Outdoor dining

Distiller's Dream - Bourbon Trail Country Fun - 12 minutes to Bardstown Square

Distiller's Dream - Bourbon Trail Country Fun - 12 minutes to Bardstown Square
Coxs Creek
10.0 out of 10, Exceptional, (16 reviews)
"The house was beautiful and clean and we had a great time on our trip. Would stay again"
United States
Nick F.
The price is AED 1,774
AED 3,600 total
includes taxes & fees
1 Jun - 2 Jun
Distiller's Dream - Bourbon Trail Country Fun - 12 minutes to Bardstown Square
Dining

3.7 Acre Estate w/ Heated Pool, 5 Kings-2 Game Rms

3.7 Acre Estate w/ Heated Pool, 5 Kings-2 Game Rms
La Grange
10.0 out of 10, Exceptional, (21 reviews)
"We had a wonderful stay!"
United States
Katie H.
The price is AED 1,979
AED 4,671 total
includes taxes & fees
10 Jun - 11 Jun
3.7 Acre Estate w/ Heated Pool, 5 Kings-2 Game Rms
Smart TV, fireplace, printers

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, (53 reviews)
"Great place!"
United States
Nakoma F.
The price is AED 579
AED 1,345 total
includes taxes & fees
25 May - 26 May
Near Highways and a 20 Min Drive to Louisville's Main Attractions
Dining

Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!

Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!
Jeffersontown
9.6 out of 10, Exceptional, (32 reviews)
"We had a wonderful experience. The house was great and had everything we needed. Everything was clean and well maintained. The host was very friendly, responsive, and flexible, which we really appreciated. Would definitely stay again!"
United States
Dieudonne N.
The price is AED 1,319
AED 2,725 total
includes taxes & fees
20 May - 21 May
Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!
Fridge, microwave, oven, stovetop

Charming house in one of Louisville's most coveted neighborhoods NO CLEANING FEE

Charming house in one of Louisville's most coveted neighborhoods NO CLEANING FEE
Louisville
10.0 out of 10, Exceptional, (83 reviews)
"Host was accommodating and welcoming. "
United States
Bobbie S.
The price is AED 694
AED 908 total
includes taxes & fees
25 May - 26 May
Charming house in one of Louisville's most coveted neighborhoods NO CLEANING FEE
Exterior

Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!

Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Louisville
9.8 out of 10, Exceptional, (81 reviews)
"We brought a large group to a conference in Louisville and it was perfect to have all of us stay together. It was a historic house, full of charm. Only negative was the warm water ran out quickly with so many people."
United States
Benjamin T.
The price is AED 2,479
AED 4,745 total
includes taxes & fees
25 May - 26 May
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Exterior

NEW, Norton Commons, Bourbon, Horses, Golf Nearby Local Dining, Fully Loaded

NEW, Norton Commons, Bourbon, Horses, Golf Nearby Local Dining, Fully Loaded
Prospect
10.0 out of 10, Exceptional, (4 reviews)
"Great location, great communication, great valueWould stay againThank you"
United States
Scott M.
The price is AED 1,349
AED 3,010 total
includes taxes & fees
20 May - 21 May
NEW, Norton Commons, Bourbon, Horses, Golf Nearby Local Dining, Fully Loaded
Exterior

NEW Pet Friendly, WiFi, Bourbon Trail, Downtown Local Dining, Fully Loaded

NEW Pet Friendly, WiFi, Bourbon Trail, Downtown Local Dining, Fully Loaded
Prospect
10.0 out of 10, Exceptional, (13 reviews)
"Great home, excellent location, easy communication with the host-looking forward to a return trip!"
United States
Kurt F.
The price is AED 1,356
AED 2,731 total
includes taxes & fees
20 May - 21 May
NEW Pet Friendly, WiFi, Bourbon Trail, Downtown Local Dining, Fully Loaded
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

Derby City Gaming & Hotel - A Churchill Downs Property

Derby City Gaming & Hotel - A Churchill Downs Property

10/10 Excellent
"It was great"
Kimberly 2-night trip
Posted 6 hours ago
Derby City Gaming & Hotel - A Churchill Downs Property