Simpsonville Holiday Rentals

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Simpsonville holiday rentals

TV

Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
Shelbyville
10.0 out of 10, Exceptional, (19 reviews)
"The Stables suite was perfect for an extended stay in Shelbyville. Great location and wonderful place to stay. "
United States
Kim K.
The price is HK$744
HK$1,434 total
includes taxes & fees
18 May - 19 May
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
Fridge, microwave, oven, stovetop

Quiet Downtown Maple Cottage Gem

Quiet Downtown Maple Cottage Gem
Shelbyville
The price is HK$986
HK$2,747 total
includes taxes & fees
13 May - 14 May
Quiet Downtown Maple Cottage Gem
Fridge, microwave, oven, stovetop

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 HK$566
HK$1,477 total
includes taxes & fees
13 May - 14 May
Whiskey Stop-Close to Ky Expo, Walkable & Parking!
Smart TV, books

Cozy Riverside Apt. Min to Downtown Louisville. King Bed, Coffee Bar!

Cozy Riverside Apt. Min to Downtown Louisville. King Bed, Coffee Bar!
Jeffersonville
9.6 out of 10, Exceptional, (36 reviews)
"This little apartment was great for what we needed! Clean, efficient, fast communication with the host, and right on the river near cute shops and restaurants. The washer/dryer was a great bonus. "
United States
Courtney
The price is HK$548
HK$1,239 total
includes taxes & fees
25 May - 26 May
Cozy Riverside Apt. Min to Downtown Louisville. King Bed, Coffee Bar!
Smart TV, books

Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee!

Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee!
Clifton
10.0 out of 10, Exceptional, (33 reviews)
"Our stay was very pleasant, great location, lots of great restaurants. Tyler the host was was always available when we had an issue. "
United States
Max D.
The price is HK$470
HK$1,409 total
includes taxes & fees
18 May - 19 May
Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee!
Fridge, microwave, oven, stovetop

Top Floor Apt Near Churchill Downs & Expo Center

Top Floor Apt Near Churchill Downs & Expo Center
Audubon
10.0 out of 10, Exceptional, (3 reviews)
"Super unique spot with great ambiance and energy! You can tell the hosts put a lot of time into making it a one-of-a-kind retreat. "
United States
andrew
The price is HK$484
HK$1,229 total
includes taxes & fees
13 May - 14 May
Top Floor Apt Near Churchill Downs & Expo Center
Fridge, microwave, oven, stovetop

Beautiful restored Victorian farmhouse

Beautiful restored Victorian farmhouse
Shelbyville
9.4 out of 10, Exceptional, (13 reviews)
"Great location to downtown Shelbyville. Porch is awesome!!"
United States
Alison L.
The price is HK$1,726
HK$3,490 total
includes taxes & fees
13 May - 14 May
Beautiful restored Victorian farmhouse
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)
"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 HK$1,722
HK$4,814 total
includes taxes & fees
13 May - 14 May
Bourbon Trail Retreat: Hot Tub & Game Room
Bar (on property)

Unique Downtown Studio with an Industrial Vibe

Unique Downtown Studio with an Industrial Vibe
Shelbyville
10.0 out of 10, Exceptional, (31 reviews)
"The VRBO was perfect. Has the elegant modern feel just like the pictures show and has lots of space to hang out and relax. Loved the location and how walkable it was to coffee shops, restaurants, and bars. Loved staying here and highly recommend!"
United States
Lucas L.
The price is HK$1,002
HK$1,730 total
includes taxes & fees
3 Jun - 4 Jun
Unique Downtown Studio with an Industrial Vibe
Interior

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 HK$1,057
HK$1,899 total
includes taxes & fees
14 May - 15 May
Carriage House, 7 minutes from downtown Louisville
Exterior

LUX Farmhouse on Bourbon Trail! Hot tub, Game Room, Firepit, Yard Games, 5-Acres

LUX Farmhouse on Bourbon Trail! Hot tub, Game Room, Firepit, Yard Games, 5-Acres
Bagdad
9.6 out of 10, Exceptional, (12 reviews)
"I had my bachelor party here and it was the perfect place to get away!"
United States
Kyser M.
The price is HK$1,389
HK$4,431 total
includes taxes & fees
13 May - 14 May
LUX Farmhouse on Bourbon Trail! Hot tub, Game Room, Firepit, Yard Games, 5-Acres
Smart TV, books

OG Highlands Home, Walkable & priv parking!

OG Highlands Home, Walkable & priv parking!
Germantown
10.0 out of 10, Exceptional, (60 reviews)
"Everything was wonderful - house nicelyDecorated & very large &Well appointed. Nice location easy to get all around Louisville "
United States
Pamela L.
The price is HK$676
HK$1,876 total
includes taxes & fees
13 May - 14 May
OG Highlands Home, Walkable & priv parking!
TV

American Pharoah Twin Spires Suite

American Pharoah Twin Spires Suite
Jeffersonville
10.0 out of 10, Exceptional, (2 reviews)
"Very accommodating...easy to communicate wit"
United States
Chris L.
The price is HK$626
HK$1,116 total
includes taxes & fees
13 May - 14 May
American Pharoah Twin Spires Suite
Smart TV

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 HK$822
HK$2,108 total
includes taxes & fees
13 May - 14 May
Close to Everything in Louisville!!!
Exterior

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 HK$673
HK$3,217 total
includes taxes & fees
31 May - 1 Jun
St. Matthew’s - Walk to Shops & Restaurants
Dining

Putt Putt House by Louisville Walking Bridge

Putt Putt House by Louisville Walking Bridge
Jeffersonville
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful property in lovely area "
United States
A. Dawn
The price is HK$783
HK$2,318 total
includes taxes & fees
31 May - 1 Jun
Putt Putt House by Louisville Walking Bridge
Iron/ironing board, WiFi, bed sheets

Alfesco - Walkable Highlands Guesthouse

Alfesco - Walkable Highlands Guesthouse
Deer Park
8.6 out of 10, Excellent, (11 reviews)
"Great communication, accommodations, and location- Trifecta! "
United States
Lisa K.
The price is HK$423
HK$1,122 total
includes taxes & fees
2 Jun - 3 Jun
Alfesco - Walkable Highlands Guesthouse
Property grounds

Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill

Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill
Crescent Hill
10.0 out of 10, Exceptional, (125 reviews)
"Really nice unit. Very comfortable and clean. Very nice area -"
United States
Harry
The price is HK$1,018
HK$1,845 total
includes taxes & fees
20 May - 21 May
Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill
TV, stereo, offices

Exquisite Condo with Views in Trendy NuLu District

Exquisite Condo with Views in Trendy NuLu District
Downtown Louisville
10.0 out of 10, Exceptional, (11 reviews)
"Perfect spot for a family looking for the comforts of home while traveling. Lots of restaurants nearby just a walk or shirt driveways. Very easy to navigate everywhere we planned to go during our stay in town. "
United States
Abigail
The price is HK$695
HK$1,826 total
includes taxes & fees
13 May - 14 May
Exquisite Condo with Views in Trendy NuLu District
Fridge, microwave, oven, stovetop

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 HK$869
HK$1,292 total
includes taxes & fees
10 Jun - 11 Jun
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
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

Birch Hill Suites Louisville

Birch Hill Suites Louisville

6/10 Okay
"."
Jihad 6-night trip
Posted 8 hours ago
Birch Hill Suites Louisville

Find out more about Simpsonville

Search for holiday rentals in Simpsonville on Expedia! You can easily find your home rentals, villas, holiday apartments in Simpsonville using one of the methods below:

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Look no further and take a look at our great range of rental properties in Simpsonville!

Frequently asked questions

Can I find a holiday rental in Simpsonville?

Yes, there are holiday rentals close to the most popular sights in Simpsonville, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Simpsonville has to offer?

Newly renovated 4BR CozySuites: This holiday home rental outside Simpsonville is equipped with a garden, air conditioning and free WiFi to help you feel comfortable during your stay. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Simpsonville?

Choose from 10 Expedia holiday rentals in Simpsonville for a memorable holiday.

What’s there to see and do in Simpsonville?

While exploring the area, visit family-friendly sights like Louisville Zoo, or get outside and enjoy nature at Beckley Creek Park. The Outlet Shoppes of the Bluegrass and Whitney M. Young, Jr. Birthplace are other places to visit while you're in town.

What’s a holiday rental in Simpsonville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Simpsonville. Holiday rentals offer extras like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for family trips or small group gatherings.