Book Holiday Homes in Simpsonville

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Featured Holiday Homes in Simpsonville

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 KY
When you stay at this vacation home in Shelbyville, you'll be 11 minutes by car from The Outlet Shoppes of the Bluegrass.
Opens in a new windowParris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE

RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE

Pendleton KY
The price is AU$347 per night from 27 Dec to 28 Dec
AU$347
27 Dec - 28 Dec
includes taxes & fees
Located in Pendleton, this vacation home is in a rural location, within a 15-minute drive of Morgan Conservation Park and LaGrange Main Street Visitor ...
Opens in a new windowRETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
Spectacular waterfront house!

Spectacular waterfront house!

Prospect KY
Located in Prospect, this vacation home is on the waterfront, within a 15-minute drive of Ohio River Valley and Paddock Shops.
Opens in a new windowSpectacular waterfront house!
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7Br/4Ba - 4k Ft - Updated Gorgeous Historic Home

7Br/4Ba - 4k Ft - Updated Gorgeous Historic Home

Louisville KY
With a stay at this vacation home in Louisville (Clifton), you'll be within a 5-minute drive of Kentucky International Convention Center and KFC Yum Center.
Opens in a new window7Br/4Ba - 4k Ft - Updated Gorgeous Historic Home
Charming Private Bungalow with EV Charger Near Downtown Louisville

Charming Private Bungalow with EV Charger Near Downtown Louisville

Louisville KY
With a stay at this vacation home, you'll be centrally located in Louisville, within a 5-minute drive of KFC Yum Center and Kentucky International Convention ...
Opens in a new windowCharming Private Bungalow with EV Charger Near Downtown Louisville
Large Private Home close to Bourbon Trail!/POOL/Free Firewood/Parks/Close to I65

Large Private Home close to Bourbon Trail!/POOL/Free Firewood/Parks/Close to I65

Shepherdsville KY
Located in Shepherdsville, this vacation home is in a rural location, within a 10-minute drive of McNeely Lake Park and Fairmount Falls Park.
Opens in a new windowLarge Private Home close to Bourbon Trail!/POOL/Free Firewood/Parks/Close to I65
The Caldwell - Germantown Highlands

The Caldwell - Germantown Highlands

Louisville KY
The price is AU$339 per night from 7 Jan to 8 Jan
AU$339
7 Jan - 8 Jan 2026
includes taxes & fees
With a stay at this vacation home in Louisville (Germantown), you'll be within a 5-minute drive of University of Louisville and KFC Yum Center.
Opens in a new windowThe Caldwell - Germantown Highlands
Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!

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

Louisville KY
With a stay at this vacation home in Louisville (Shelby Park), you'll be within a 5-minute drive of University of Louisville and KFC Yum Center.
Opens in a new windowRenovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!
Close to Everything in Louisville!!!

Close to Everything in Louisville!!!

Louisville KY
The price is AU$408 per night from 28 Dec to 29 Dec
AU$408
28 Dec - 29 Dec
includes taxes & fees
With a stay at this vacation home in Louisville (Camp Taylor), you'll be a 3-minute drive from Louisville Mega Cavern and 6 minutes from Kentucky Exposition ...
Opens in a new windowClose to Everything in Louisville!!!
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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.

Simpsonville Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Simpsonville vacation homes are the perfect way for you to wing it.

Holiday houses in Simpsonville let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Simpsonville in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Simpsonville adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Simpsonville with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Simpsonville vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Simpsonville Holiday Homes essential information

Accommodation
777 Holiday Homes
Lowest Price
AU$114
Highest Price
AU$408
Popular accommodation
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby, RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE, Spectacular waterfront house!, 7Br/4Ba - 4k Ft - Updated Gorgeous Historic Home, Charming Private Bungalow with EV Charger Near Downtown Louisville, Large Private Home close to Bourbon Trail!/POOL/Free Firewood/Parks/Close to I65, The Caldwell - Germantown Highlands, Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!, Close to Everything in Louisville!!!

Top trending hotels in Simpsonville

Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
830 Phillips Lane Louisville KY
Fully refundableReserve now, pay when you stay
The price is AU$164 per night from 29 Dec to 30 Dec
AU$164
29 Dec - 30 Dec
includes taxes & fees
Located in Louisville (Fairgrounds), Crowne Plaza Louisville Airport Expo Ctr by IHG is within a 15-minute walk of Kentucky Kingdom and Kentucky Exposition ...
Opens in a new windowCrowne Plaza Louisville Airport Expo Ctr by IHG
Derby City Gaming & Hotel -  A Churchill Downs Property

Derby City Gaming & Hotel - A Churchill Downs Property

4 out of 5
4520 Poplar Level Rd Louisville KY
Fully refundableReserve now, pay when you stay
When you stay at Derby City Gaming & Hotel - A Churchill Downs Property in Louisville, you'll be near the airport, within a 10-minute drive of Louisville Mega ...
Opens in a new windowDerby City Gaming & Hotel - A Churchill Downs Property
Wingate by Wyndham Louisville Fair and Expo

Wingate by Wyndham Louisville Fair and Expo

2.5 out of 5
3200 Kemmons Drive Louisville KY
Fully refundableReserve now, pay when you stay
The price is AU$114 per night from 25 Jan to 26 Jan
AU$114
25 Jan - 26 Jan 2026
includes taxes & fees
With a stay at Wingate by Wyndham Louisville Fair and Expo in Louisville (Hayfield Dundee), you'll be a 5-minute drive from Louisville Mega Cavern and 7 minutes ...
Opens in a new windowWingate by Wyndham Louisville Fair and Expo
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Hilton Garden Inn Louisville/Northeast

Hilton Garden Inn Louisville/Northeast

3 out of 5
9850 Park Plaza Ave Louisville KY
Fully refundableReserve now, pay when you stay
The price is AU$152 per night from 2 Jan to 3 Jan
AU$152
2 Jan - 3 Jan 2026
includes taxes & fees
Located in Louisville, Hilton Garden Inn Louisville/Northeast is connected to a shopping center, a 1-minute drive from Paddock Shops and 11 minutes from Mall ...
Opens in a new windowHilton Garden Inn Louisville/Northeast
Don't see what you're looking for?
See all available properties in Simpsonville
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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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^Subject to availability and chosen travel dates.