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Compare 656 Vacation Homes in Simpsonville with updated reviews, rates, and availability.

Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill

9.8 out of 10, Exceptional, (13)
"My brother and I and our spouses stayed here as a base for exploring bourbon distilleries. The house was perfect for us and was beautifully decorated. I regret not using the hot tub and fire pit but the snow and cold weather was too much to hang out outdoors! "
Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill

Home Sweet Hayden - 4 beds/3 Full Bath in East End

10.0 out of 10, Exceptional, (36)
"This home was exactly what you hoped for when searching for a short, stay location. Reasonably priced, extraordinarily clean, and well furnished."
Home Sweet Hayden - 4 beds/3 Full Bath in East End

Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!

10.0 out of 10, Exceptional, (83)
"My family stayed here while visiting Louisville for the National Farm Machinery show. There was plenty of space for our group of 9!"
The price is AED 735
AED 1,868 total
includes taxes & fees
25 Mar - 26 Mar
Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!

New! Kings on Restaurant Row! HotTub!Close to NuLu

8.8 out of 10, Excellent, (18)
"Great location. Modern updates with a ton of character. "
New! Kings on Restaurant Row! HotTub!Close to NuLu

Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby

9.2 out of 10, Wonderful, (14)
"Everything you could need is here. Very clean. I would recommend if you are vertically challenged like myself you bring a step stool if you are planning to get in the master bed. I stayed here because it was pet friendly and I was being my dog to Louisville for a surgery. It was perfect for what we needed. "
The price is AED 364
AED 801 total
includes taxes & fees
2 Mar - 3 Mar
Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby

Preston Retreat - Convenient Germantown Location

The price is AED 320
AED 889 total
includes taxes & fees
2 Mar - 3 Mar
Preston Retreat - Convenient Germantown Location

Peaceful Contemporary Close to Everything

10.0 out of 10, Exceptional, (39)
"Great place to stay while we attended class at Moonshine University and toured some distilleries downtown! "
The price is AED 764
AED 1,668 total
includes taxes & fees
3 Mar - 4 Mar
Peaceful Contemporary Close to Everything

New! The Old Timer - 5BR/4.5BA - Hot Tub! Historic!

9.4 out of 10, Exceptional, (21)
"Nice location, super cool place, would stay again! "
New! The Old Timer - 5BR/4.5BA - Hot Tub! Historic!

3 BR Downtown Sanctuary! Huge back yard

8.6 out of 10, Excellent, (26)
"The property was in a convenient location for our stay. We went to the Louisville Mega Caverns, the Ohio River Falls, the Kentucky Derby Museum, Derby Downs Casino. We had 6 adults and the place was roomy for us all"
The price is AED 371
AED 847 total
includes taxes & fees
2 Mar - 3 Mar
3 BR Downtown Sanctuary! Huge back yard

THE BARRET HOUSE, 2 floor luxury home, LOCATION! Downtown, HIGHLANDS, NuLu, EXPO

10.0 out of 10, Exceptional, (72)
"I am not able to fully rate the property, since we were unable to stay here due to the significant snowfall in Louisville. Despite that, I did want to pass along praise for the host, James! He was a great communicator throughout and incredibly helpful in every way! 5 stars for James and I hope to return and stay at this property and explore Louisville (without snow!!) in the future!"
THE BARRET HOUSE, 2 floor luxury home, LOCATION! Downtown, HIGHLANDS, NuLu, EXPO

The Highlands Hideaway, 50 steps from Restaurant Row, Downtown, Expo, Highlands

10.0 out of 10, Exceptional, (144)
"James and the property were both outstanding! It was really fun to stay in such a cool house! The Highlands area is busy in all the best ways! Off-street parking was so helpful and made our stay very easy. The shops, restaurants, spa, people, and energy were welcoming and friendly. I wouldn't recommend going anywhere else if you and your peeps need a quick, fun getaway!!"
The Highlands Hideaway, 50 steps from Restaurant Row, Downtown, Expo, Highlands

Charming Private Bungalow with EV Charger Near Downtown Louisville

10.0 out of 10, Exceptional, (77)
"Well stocked full kitchen, comfortable bed, covered parking. Nice size for two. Say “hi” to Mike for us if you stay!"
Charming Private Bungalow with EV Charger Near Downtown Louisville

Riverview balcony. Historic dwntn Jeffersonville. 1 mile from dwntn Louisville.

10.0 out of 10, Exceptional, (2)
"I was really impressed with this beautifully restored historic property. It was very clean and included some very welcoming touches. I want to come back this summer and enjoy both decks. A wonderful spot to enjoy downtown Jeff when it’s really hoppin."
The price is AED 511
AED 1,228 total
includes taxes & fees
2 Mar - 3 Mar
Riverview balcony. Historic dwntn Jeffersonville. 1 mile from dwntn Louisville.

NEW: Hot Tub, Pool, Fully Loaded, 10 min to Bulleit, Between LOU and LEX.

10.0 out of 10, Exceptional, (1)
"Our stay at the Bourbon Bungalow was a fantastic experience for our group of three families! The property is in a peaceful, rural spot across from Guist Creek Lake, offering a relaxing atmosphere and perfect access to the Bourbon Trail.The house is incredibly spacious and thoughtfully designed. Each of the four bedrooms is themed after a local distillery, adding a unique, fun touch. The Woodford and Buffalo Trace rooms, both with king beds and en-suite baths, were hits for the adults. The...
The price is AED 698
AED 1,928 total
includes taxes & fees
4 Mar - 5 Mar
NEW: Hot Tub, Pool, Fully Loaded, 10 min to Bulleit, Between LOU and LEX.

River City Retreat

9.8 out of 10, Exceptional, (8)
"We felt comfortable in this home"
River City Retreat

Cheerful Historical Mansion 8-bedrooms and 6 baths Vacation Home in Derby City

9.8 out of 10, Exceptional, (63)
"Very neat place. Very satisfying for all of us."
The price is AED 2,494
AED 4,762 total
includes taxes & fees
2 Mar - 3 Mar
Cheerful Historical Mansion 8-bedrooms and 6 baths Vacation Home in Derby City

Historic District Townhouse in City's BEST Location

9.8 out of 10, Exceptional, (186)
"Huge well appointed townhouse, nicely decorated and some of the most comfortable beds we have ever slept in!Restaurants, bars, art and coffee right out your front door. Rent this place. "
Historic District Townhouse in City's BEST Location

☆Stunning Derby Home☆ 5 KING BEDS, HOT TUB,FIREPIT

9.0 out of 10, Wonderful, (20)
"Wonderful set up for our ladies weekend. Tyler was easy to work with and very responsive. Jeffersonville is a hidden gem!"
The price is AED 395
AED 1,332 total
includes taxes & fees
4 Mar - 5 Mar
☆Stunning Derby Home☆ 5 KING BEDS, HOT TUB,FIREPIT

River City Retreat near Zoo/Expo/Airport/Churchill + Arcade

9.8 out of 10, Exceptional, (55)
"We took a short weekend trip to Louisville to go on some Bourbon tours and this place was perfect. Nearby to many tours and breweries. Quiet neighborhood, very clean with smart TVs, and very responsive! Would definitely stay again!"
River City Retreat near Zoo/Expo/Airport/Churchill + Arcade

Updated 3 Bedroom Centrally Located Near Downtown

9.2 out of 10, Wonderful, (30)
"Good place, easy parking and right price. Thank you "
The price is AED 378
AED 1,202 total
includes taxes & fees
9 Mar - 10 Mar
Updated 3 Bedroom Centrally Located Near Downtown
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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Other property types in Simpsonville

Hancock House

3.0 star property
8.0 out of 10, Very Good, (213)
"cleaning staff was very helpful"
The price is AED 322
AED 587 total
includes taxes & fees
3 Mar - 4 Mar
Hancock House

Stellar Suites

4.5 star property
9.6 out of 10, Exceptional, (91)
"Outstanding!"
The price is AED 430
AED 690 total
includes taxes & fees
30 Mar - 31 Mar
Stellar Suites

The Bellwether Hotel

2.0 star property
8.0 out of 10, Very Good, (11)
"Beautifully redone historic building. Enjoyed design features and Christmas decor! Great walkable neighborhood. "
The price is AED 537
AED 624 total
includes taxes & fees
28 Feb - 1 Mar
The Bellwether Hotel
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.