Simpsonville, KY Vacation Homes from AED 594

Simpsonville Vacation Homes
Louisville
Kentucky
United States of America
Expedia.ae

A brick clock tower with two clocks, surrounded by dense foliage.

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Our top choices for Simpsonville vacation homes

A dining area with a marble table and blue upholstered chairs, a kitchen with modern appliances, and a view of the outdoors through large windows.

A residential property with a two-story house, a covered patio, and a driveway.

A residential backyard with a grassy lawn, a concrete pathway leading to a covered porch, and a staircase to an upper level.

A garage with a concrete floor and a white door.

1. Spacious Bourbon retreat near Downtown Louisville!

Spacious Bourbon retreat near Downtown Louisville!

Simpsonville

The price is AED 577

AED 577

AED 1,534 total

includes taxes & fees

18 Oct - 19 Oct

Spacious Bourbon retreat near Downtown Louisville!

A two-story house with a porch, a small garden, and a sign that reads "Hotel."

A dining area with a black table and white chairs, a chandelier, and a window with white shutters.

A modern kitchen with white cabinets, a marble floor, a farmhouse-style accent wall, and a kitchen island with a towel rack.

A living room with two grey sofas, a white coffee table, a fireplace, and a staircase leading to another room.

2. 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

9.4 out of 10, Exceptional, (50 reviews)

9.4/10

Exceptional

(50 reviews)

"Great house and location. Enjoyed our stay. Would use this location again."

Donald A.

The price is AED 555

AED 555

AED 1,104 total

includes taxes & fees

25 Oct - 26 Oct

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

A hot tub with a glass of red wine, surrounded by a lush green outdoor setting.

A modern kitchen with white cabinets, a built-in dishwasher, a window with blinds, and various kitchen items on the counter.

A two-story house with a front porch, columns, and a red door.

A modern living room with a black leather sofa, brown armchairs, a round coffee table, and a flat-screen TV mounted on the wall.

3. Bourbon Trail! Game Room Hot Tub Speakeasy FirePit

Bourbon Trail! Game Room Hot Tub Speakeasy FirePit

Shelbyville

10.0 out of 10, Exceptional, (23 reviews)

10/10

Exceptional

(23 reviews)

"Great location perfect house to enjoy"

tim d.

The price is AED 1,960

AED 1,960

AED 2,486 total

includes taxes & fees

27 Oct - 28 Oct

Bourbon Trail! Game Room Hot Tub Speakeasy FirePit

A living room with a fireplace, a sofa, a coffee table, and a dining area with a table and chairs.

A cozy bedroom with a large bed, a bookshelf, a desk, and a window with curtains.

A spacious living room with a wooden coffee table, a sofa with red and white cushions, and a dining area with a wooden table and chairs.

A two-story brick house with a front porch, garage, and a small garden with a birdbath.

4. 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, (58 reviews)

10/10

Exceptional

(58 reviews)

"This is the second time we’ve stayed a long weekend here and plan to do so again in the future! Highly recommended!"

Clint S.

The price is AED 661

AED 661

AED 1,514 total

includes taxes & fees

29 Oct - 30 Oct

Near Highways and a 20 Min Drive to Louisville's Main Attractions

A modern kitchen with wooden cabinets, a marble countertop, and a dining area with a round table and chairs.

A bedroom with a bed, dresser, ceiling fan, and a TV on the wall.

A modern kitchen with wooden cabinets, stainless steel appliances, and a granite countertop.

A spacious living room with a large gray sectional sofa, wooden flooring, a ceiling fan, and a flat-screen TV mounted on the wall.

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

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

Jeffersontown

9.2 out of 10, Wonderful, (40 reviews)

9.2/10

Wonderful

(40 reviews)

"Great close to everything clean place definitely recommend "

Jefferey S.

The price is AED 1,319

AED 1,319

AED 2,631 total

includes taxes & fees

18 Oct - 19 Oct

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

A modern kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a marble countertop.

A dining table set with plates and placemats, surrounded by chairs, in a room with wooden cabinets and a window.

A modern kitchen with a built-in refrigerator, a dining area with a table set for two, and a green plant in the foreground.

A patio with Adirondack chairs and a table, a screened porch, and a view of a house and greenery.

6. Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views

Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views

Waddy

9.0 out of 10, Wonderful, (12 reviews)

9.0/10

Wonderful

(12 reviews)

"Excellent stay and a beautiful property. Perfect for our needs no complaints."

Anthony T.

The price is AED 393

AED 393

AED 1,285 total

includes taxes & fees

21 Oct - 22 Oct

Cozy Bourbon Trail Stay | Jacuzzi Tub & Best Views

A modern kitchen with a central island, stainless steel appliances, and a large window providing natural light.

A white building with a porch and four white Adirondack chairs facing a grassy field.

A kitchen with a central island, a double sink, and a dining area in the background.

A living room with a sectional sofa, a coffee table, and a TV mounted on the wall.

7. Ridge View Villa #1 -Haven in the Heart of the Bourbon Trail.

Ridge View Villa #1 -Haven in the Heart of the Bourbon Trail.

Waddy

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"The place was great. Tucked away off the main highway and between bourbon country’s best. Well stocked amenities and little things provided that were a great touch. Will be back again!"

Daniel H.

The price is AED 437

AED 437

AED 1,022 total

includes taxes & fees

27 Oct - 28 Oct

Ridge View Villa #1 -Haven in the Heart of the Bourbon Trail.

A modern kitchen with a large window, a dining area with a table and chairs, and a view of the outdoors.

A dining area with a white table, black chairs, a chandelier, and a window with a view of greenery.

A modern living room with a fireplace, a sofa, a coffee table, and a TV mounted above the fireplace.

A stone house with a porch, a chimney, and a staircase leading to the entrance.

8. Charming house in one of Louisville's most coveted neighborhoods

Charming house in one of Louisville's most coveted neighborhoods

Louisville

10.0 out of 10, Exceptional, (87 reviews)

10/10

Exceptional

(87 reviews)

"Enjoyed the location and quiet neighborhood. You will not be one disappointed."

Tania B.

The price is AED 837

AED 837

AED 1,479 total

includes taxes & fees

19 Oct - 20 Oct

Charming house in one of Louisville's most coveted neighborhoods

A marina with boats docked, a covered seating area, and a building with a distinctive sun emblem.

A swimming pool with a deck, lounge chairs, and a small building.

A covered patio with two rocking chairs and a table, overlooking a scenic landscape.

A single-story house with a red door, a small porch, and a tree in the front yard.

9. #29 Angels Envy Lakefront Home with Hot Tub and Resort Pool

#29 Angels Envy Lakefront Home with Hot Tub and Resort Pool

Taylorsville

9.0 out of 10, Wonderful, (30 reviews)

9.0/10

Wonderful

(30 reviews)

"Very clean. Nice place! Recommended"

Anonymous traveler

The price is AED 573

AED 573

AED 1,269 total

includes taxes & fees

1 Nov - 2 Nov

#29 Angels Envy Lakefront Home with Hot Tub and Resort Pool

A kitchen with wooden cabinets, a stove, a microwave, a sink, and a refrigerator.

A room with a beige wall, a white sofa with multiple cushions, a small table, and a window with a curtain.

A room with a bed, a television, a desk, and a chair.

A covered patio with a table and chairs, a window with green trim, and a brick wall.

10. St. Matthew’s - Walk to Shops & Restaurants

St. Matthew’s - Walk to Shops & Restaurants

St. Matthews

9.0 out of 10, Wonderful, (14 reviews)

9.0/10

Wonderful

(14 reviews)

"cute housegreat location easy peasy"

Lisa M.

The price is AED 364

AED 364

AED 1,334 total

includes taxes & fees

1 Nov - 2 Nov

St. Matthew’s - Walk to Shops & Restaurants

A large rectangular swimming pool with a deck, surrounded by a white fence. There are lounge chairs and a small patio area with tables and chairs.

A hot tub with a view of a forested area.

A residential area with houses, a driveway, and a blue car parked on the street.

11. #18 Kentucky Sunrise - Lakefront Home with spacuios patio and Hot Tub

#18 Kentucky Sunrise - Lakefront Home with spacuios patio and Hot Tub

Taylorsville

9.8 out of 10, Exceptional, (56 reviews)

9.8/10

Exceptional

(56 reviews)

"Excellent view and cozy home"

Adam D.

The price is AED 724

AED 724

AED 1,435 total

includes taxes & fees

1 Nov - 2 Nov

#18 Kentucky Sunrise - Lakefront Home with spacuios patio and Hot Tub

A hot tub with a floating platform, surrounded by a deck with chairs and string lights.

A modern kitchen with wooden flooring, a dining area with a wooden table and chairs, a kitchen island, and a large window providing natural light.

12. Seabiscuit 5- Relax And Kick Back with private Hot Tub and communal Pool

Seabiscuit 5- Relax And Kick Back with private Hot Tub and communal Pool

Taylorsville

9.6 out of 10, Exceptional, (57 reviews)

9.6/10

Exceptional

(57 reviews)

"We thoroughly enjoyed our stay. The house was the perfect size for our group, the hot tub was great after a long day, and the game was an added bonus!"

Lisa L.

The price is AED 646

AED 646

AED 1,176 total

includes taxes & fees

1 Nov - 2 Nov

Seabiscuit 5- Relax And Kick Back with private Hot Tub and communal Pool

A bedroom with a bed, nightstands, a ceiling fan, and a window with shutters.

A living room with a fireplace, a television mounted above it, and a door with a mirror.

A kitchen with white cabinets, a stainless steel refrigerator, a built-in oven, a granite countertop, and a hanging light fixture.

A wooden deck with a sofa, a small table, and a potted plant.

13. Convenient & Cozy! Close to everything Louisville!

Convenient & Cozy! Close to everything Louisville!

Belknap

Convenient & Cozy! Close to everything Louisville!

A living room with a sofa, armchair, coffee table, and a dining area with a table and chairs.

A living room with a couch, armchair, coffee table, and a small table with a lamp. There is a kitchen in the background with cabinets and a clock on the wall.

A single-story house with a red door, a front porch, and a mailbox.

A modern kitchen with white cabinets, a wooden dining table, and a vintage clock.

14. The Whiskey Stop! A Spacious Highlands Retreat

The Whiskey Stop! A Spacious Highlands Retreat

Germantown

10.0 out of 10, Exceptional, (79 reviews)

10/10

Exceptional

(79 reviews)

"It was perfect for our stay very comfortable and we enjoyed it very much"

Lester W.

The price is AED 375

AED 375

AED 862 total

includes taxes & fees

15 Nov - 16 Nov

The Whiskey Stop! A Spacious Highlands Retreat

A modern kitchen with white cabinets, a dining table set for four, and a black patterned curtain.

A kitchen with white cabinets, a dishwasher, an oven, a coffee maker, and a window with a curtain.

A neatly made bed with rolled towels, colorful pillows, and a yellow blanket.

A living room with a green sofa, a wooden coffee table, an orange armchair, a TV on a stand, and a patterned rug.

15. 3-BDR King Suite in Mount Washington Fenced yard minutes from Louisville

3-BDR King Suite in Mount Washington Fenced yard minutes from Louisville

Mount Washington

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"We had a great experience with the host and the property. We would rent this again."

Meghan T.

The price is AED 532

AED 532

AED 907 total

includes taxes & fees

25 Oct - 26 Oct

3-BDR King Suite in Mount Washington Fenced yard minutes from Louisville

A wooden cabin with a green roof, surrounded by lush greenery and a gravel path.

A stone pathway leading to a wooden building with a covered patio area, surrounded by lush greenery and a large tree.

A brick pathway leading to a house with a covered patio area.

A cozy living room with a leather sofa, a patterned ottoman, a fireplace, and a bookshelf filled with books.

16. 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, (87 reviews)

9.8/10

Exceptional

(87 reviews)

"We had a great time! "

Amber H.

The price is AED 2,479

AED 2,479

AED 4,745 total

includes taxes & fees

2 Nov - 3 Nov

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

A wooden deck with a green door, wicker chairs, and a small table.

A two-story house with a front porch, a staircase, and a mailbox marked with the number 211.

A hallway with a fireplace, a sofa, and a black door.

A bedroom with a large bed, a fireplace, a TV, and a window with curtains.

17. The Sweet Retreat Wheelchair Accessible Historic Home

The Sweet Retreat Wheelchair Accessible Historic Home

La Grange

10.0 out of 10, Exceptional, (7 reviews)

10/10

Exceptional

(7 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!"

Shelley S.

The price is AED 988

AED 988

AED 1,708 total

includes taxes & fees

1 Nov - 2 Nov

The Sweet Retreat Wheelchair Accessible Historic Home

A spacious kitchen with a large island, wooden cabinets, and a high ceiling with exposed beams.

A dining area with a round table, four chairs, a vase with flowers, and a corkboard on the wall.

A bedroom with a bed, a ceiling fan, a window, and a door.

A modern kitchen with a central island, stainless steel sink, and wooden cabinets.

18. 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, (26 reviews)

10/10

Exceptional

(26 reviews)

"The carriage house was very roomy and nice. We would definitely stay here again."

Pam

The price is AED 397

AED 397

AED 594 total

includes taxes & fees

20 Oct - 21 Oct

Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

A patio with a table and chairs, surrounded by a wooden fence and tall, conical trees.

A living room with a TV displaying 'NETFLIX,' a round mirror, a potted plant, and a cozy chair.

A modern kitchen with a stainless steel refrigerator, wooden dining table, and dark cabinetry.

A bedroom with a bed, bedside lamps, a painting, and a wooden dresser.

19. Bourbon Belle- Cozy Germantown home with parking!

Bourbon Belle- Cozy Germantown home with parking!

Germantown

10.0 out of 10, Exceptional, (79 reviews)

10/10

Exceptional

(79 reviews)

"We've stayed here a few times in the past and it's always been a great experience!"

Paul H.

The price is AED 224

AED 224

AED 667 total

includes taxes & fees

2 Nov - 3 Nov

Bourbon Belle- Cozy Germantown home with parking!

A living room with a grey sofa, blue ottoman, and a ceiling fan.

A two-story building with a garage entrance, a car parked in front, and a clear sky.

A front door with a teal color, a mailbox, and a doormat with the word "WELCOME".

A kitchen with white cabinets, a stove, a microwave, and a refrigerator.

20. Walk to EVERYTHING- Top Restaurants/Shopping/Nightlife - Bardstown Rd /Highlands

Walk to EVERYTHING- Top Restaurants/Shopping/Nightlife - Bardstown Rd /Highlands

Louisville

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"Great little spot, and communication with the host was phenomenal!"

Kate J.

Walk to EVERYTHING- Top Restaurants/Shopping/Nightlife - Bardstown Rd /Highlands

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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