Simpsonville Holiday Rentals

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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Simpsonville holiday rentals

Smart TV

Cottage in Shelbyville

KY Bourbon Trail Home, King Bed, FirePit, Near Louisville
9.8 out of 10, Exceptional, (8 reviews)
"The perfect location for a quick stop on the bourbon trail. Ten minutes from Bulleit, down the road from Jeptha Creed, and a short hop over to Buffalo Trace and downtown Louisville!"
United States
Shay D.
The price is HK$1,102
HK$2,580 total
includes taxes & fees
20 Jan - 21 Jan
KY Bourbon Trail Home, King Bed, FirePit, Near Louisville
27-inch Smart TV with satellite channels

Aparthotel in Downtown Louisville

The Duke Hotel
2.0 star property
The price is HK$780
HK$1,295 total
includes taxes & fees
20 Jan - 21 Jan
The Duke Hotel
Outdoor dining

Cottage in Taylorsville

Bourbon Boating Lake House, 3bed, 3 bath cottage on Taylorsville Lake-Cottage 41
10.0 out of 10, Exceptional, (11 reviews)
"Clean, comfortable and convenient for our self guided bourbon trail tour. We would definitely stay there again. "
United States
Roger S.
The price is HK$1,256
HK$2,846 total
includes taxes & fees
20 Jan - 21 Jan
Bourbon Boating Lake House, 3bed, 3 bath cottage on Taylorsville Lake-Cottage 41
Outdoor dining

Holiday Home in Taylorsville

Angels Envy 29 - A relaxing place by the lake!
9.4 out of 10, Exceptional, (20 reviews)
"Great place good accommodation "
United States
Ryan D.
The price is HK$1,053
HK$2,393 total
includes taxes & fees
20 Jan - 21 Jan
Angels Envy 29 - A relaxing place by the lake!
Front of property

Aparthotel in Tyler Park

The Bellwether Hotel
3.5 star property
8.8 out of 10, Excellent, (36 reviews)
"Clean room, history and location. "
United States
RICHARD
The price is HK$952
HK$1,106 total
includes taxes & fees
20 Jan - 21 Jan
The Bellwether Hotel
Lounge

Aparthotel in Downtown Louisville

Stellar Suites
4.5 star property
9.6 out of 10, Exceptional, (119 reviews)
"The check-in process was simple and easy, the room was spotless and had so many amenities. "
United States
Grace
The price is HK$819
HK$1,358 total
includes taxes & fees
8 Feb - 9 Feb
Stellar Suites
Smart TV

Holiday Home in Camp Taylor

Close to Everything in Louisville!!!
9.4 out of 10, Exceptional, (37 reviews)
"Clean home and very friendly neighbors "
United States
Tranquilina G.
The price is HK$819
HK$2,109 total
includes taxes & fees
20 Jan - 21 Jan
Close to Everything in Louisville!!!
Iron/ironing board, WiFi, bed sheets

Apartment in Deer Park

Alfesco - Walkable Highlands Guesthouse
8.6 out of 10, Excellent, (10 reviews)
"Great communication, accommodations, and location- Trifecta! "
United States
Lisa K.
The price is HK$476
HK$1,748 total
includes taxes & fees
20 Jan - 21 Jan
Alfesco - Walkable Highlands Guesthouse
TV

Apartment in Shelbyville

Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
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$741
HK$1,428 total
includes taxes & fees
2 Feb - 3 Feb
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
Bar (on property)

Apartment in Shelbyville

Unique Downtown Studio with an Industrial Vibe
10.0 out of 10, Exceptional, (31 reviews)
"Cool place , great location . I would definitely book it again."
United States
james f.
The price is HK$834
HK$1,532 total
includes taxes & fees
17 Feb - 18 Feb
Unique Downtown Studio with an Industrial Vibe
Terrace/patio

Holiday Home in Taylorsville

Cozy KY Escape with Hot Tub near the Bourbon Trail
10.0 out of 10, Exceptional, (104 reviews)
"Very nice. Perfect cottage for the 4 of us as we did the bourbon trail. Toni Is a great hostess. "
United States
Leland J.
The price is HK$1,053
HK$2,200 total
includes taxes & fees
20 Jan - 21 Jan
Cozy KY Escape with Hot Tub near the Bourbon Trail
Fridge, microwave, oven, stovetop

Holiday Home in Charlestown

Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
10.0 out of 10, Exceptional, (12 reviews)
"Clean and was as advertised Great location for our plans "
United States
Mike A.
The price is HK$741
HK$1,145 total
includes taxes & fees
24 Jan - 25 Jan
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Dining

Holiday Home in Jeffersonville

Putt Putt House by Louisville Walking Bridge
2.0 star property
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful property in lovely area "
United States
A. Dawn
The price is HK$780
HK$2,291 total
includes taxes & fees
1 Feb - 2 Feb
Putt Putt House by Louisville Walking Bridge
Fridge, microwave, oven, stovetop

Holiday Home in Poplar Level

Private Home Close to Zoo, U of L, Churchill Downs
9.6 out of 10, Exceptional, (21 reviews)
"This house was just as described. We had everything we needed and the property manager was awesome communicating the whole time. Would definitely recommend to anyone! "
United States
Renee C.
The price is HK$694
HK$2,452 total
includes taxes & fees
22 Jan - 23 Jan
Private Home Close to Zoo, U of L, Churchill Downs
Outdoor dining

Holiday Home in Germantown

The Burnt Barrel | New HotTub & Grill | Backyard!
2.0 star property
10.0 out of 10, Exceptional, (3 reviews)
"Excellent walking to different little shops. Super decorated inside and out. Loved the hot tub. Would stay again! "
United States
kevin m.
The price is HK$763
HK$1,752 total
includes taxes & fees
20 Jan - 21 Jan
The Burnt Barrel | New HotTub & Grill | Backyard!
Exterior

Apartment in Louisville

Cozy Tree-Lined Carriage Home - Stay in Serenity!
9.8 out of 10, Exceptional, (22 reviews)
"Great place "
United States
Scott L.
The price is HK$532
HK$1,251 total
includes taxes & fees
20 Jan - 21 Jan
Cozy Tree-Lined Carriage Home - Stay in Serenity!
Interior

Holiday Home in louisville

Carriage House, 7 minutes from downtown Louisville
10.0 out of 10, Exceptional, (49 reviews)
"Clean, quiet, very comfortable. Great shower too. "
United States
Michael D.
The price is HK$1,053
HK$1,855 total
includes taxes & fees
20 Jan - 21 Jan
Carriage House, 7 minutes from downtown Louisville
Exterior

Holiday Home in St. Matthews

St. Matthew’s - Walk to Shops & Restaurants
8.8 out of 10, Excellent, (8 reviews)
"Stayed for a friends wedding at Whitehall. Location was great and we were able to walk to a handful of restaurants and coffee shops "
United States
Natalie H.
The price is HK$624
HK$2,109 total
includes taxes & fees
15 Feb - 16 Feb
St. Matthew’s - Walk to Shops & Restaurants
Terrace/patio

Holiday Home in Pendleton

RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
9.8 out of 10, Exceptional, (62 reviews)
"Host was responsive to all messages. The small home we stayed in was so cozy and clean. Directions on how to get there were clear and easy to follow. 10/10 would recommend."
United States
Haley V.
The price is HK$663
HK$1,814 total
includes taxes & fees
21 Jan - 22 Jan
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
Seasonal outdoor pool

Aparthotel in Downtown Louisville

CozySuites at Nulu
4.0 star property
8.2 out of 10, Very good, (26 reviews)
"The unit was clean, all communications were timely, the property has all the amenities, and NULU is very walkable. A perfect stay! My only regret is that I wasn't able to extend the stay. Highly recommended if you're in the Louisville area "
United States
William
The price is HK$538
HK$1,529 total
includes taxes & fees
20 Jan - 21 Jan
CozySuites at Nulu
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

SpringHill Suites by Marriott Louisville Downtown

SpringHill Suites by Marriott Louisville Downtown

10/10 Excellent
"My stay at this hotel was nothing short of outstanding. From the moment I arrived, the staff made me feel genuinely welcomed with their friendly attitudes and attention to detail. Check‑in was quick and effortless, and every interaction throughout my stay felt sincere and professional. The room was spotless, beautifully maintained, and incredibly comfortable. The bed felt like sleeping on a cloud, and the amenities were thoughtfully arranged. I especially appreciated the quiet atmosphere — perfect for relaxing after a long day. The hotel’s facilities were equally impressive. Whether it was the well-kept common areas, the inviting lobby, or the excellent breakfast selection, everything reflected a high standard of care. It’s clear that the team takes pride in creating a great guest experience. Overall, this was one of the best hotel stays I’ve had in a long time. I left feeling refreshed, appreciated, and already looking forward to returning. Highly recommended for anyone seeking comfort, quality, and exceptional service."
Kevin 1-night trip
Posted 2 days ago
SpringHill Suites by Marriott Louisville Downtown

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?

Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!: This holiday home rental outside of Simpsonville is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Simpsonville?

Choose from 8 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 IceLand Sports Complex, 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.