Simpsonville Holiday Rentals

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Our top choices for Simpsonville holiday rentals

Stellar Suites

Stellar Suites
4.5 star property
Downtown Louisville
9.6 out of 10, Exceptional, (118)
"The check-in process was simple and easy, the room was spotless and had so many amenities. "
United States
Grace
The price is NZ$305
includes taxes & fees
27 Jan - 28 Jan
Stellar Suites

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

RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
Pendleton
9.8 out of 10, Exceptional, (62)
"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 NZ$398
includes taxes & fees
12 Jan - 13 Jan
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE

Unique Downtown Studio with an Industrial Vibe

Unique Downtown Studio with an Industrial Vibe
Shelbyville
9.8 out of 10, Exceptional, (30)
"Cool place to stay & great location"
United States
Amy B.
The price is NZ$309
includes taxes & fees
4 Jan - 5 Jan
Unique Downtown Studio with an Industrial Vibe

The Bellwether Hotel

The Bellwether Hotel
3.5 star property
Tyler Park
8.8 out of 10, Excellent, (35)
"Clean room, history and location. "
United States
RICHARD
The price is NZ$216
includes taxes & fees
4 Jan - 5 Jan
The Bellwether Hotel

Book for Derby! Close to Churchill & Expo Center!

Book for Derby! Close to Churchill & Expo Center!
Germantown
10.0 out of 10, Exceptional, (71)
"Great location! Walking distance to several restaurants. Neighborhood is quite and safe. "
United States
Tracy F.
The price is NZ$334
includes taxes & fees
3 Jan - 4 Jan
Book for Derby! Close to Churchill & Expo Center!

Secretariat Twin Spires Suite!

Secretariat Twin Spires Suite!
Jeffersonville
10.0 out of 10, Exceptional, (2)
"A wonderful place in a wonderful location. Walking distance to almost everything. Host was extremely helpful and made our stay unforgettable. The unit itself is very nice with easy access in and out. Lots of parking in the back. I would definitely recommend. "
United States
Drew J.
The price is NZ$213
includes taxes & fees
1 Feb - 2 Feb
Secretariat Twin Spires Suite!

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, (12)
"The property was clean and quiet. Great location in a nice residential neighborhood. Very close to Charlestown State Park where we did some hiking."
United States
Chris S.
The price is NZ$255
includes taxes & fees
12 Jan - 13 Jan
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

Cozy Tree-Lined Carriage Home - Stay in Serenity!

Cozy Tree-Lined Carriage Home - Stay in Serenity!
Louisville
9.8 out of 10, Exceptional, (21)
"Great place "
United States
Scott L.
The price is NZ$287
includes taxes & fees
18 Jan - 19 Jan
Cozy Tree-Lined Carriage Home - Stay in Serenity!

Private Home Close to Zoo, U of L, Churchill Downs

Private Home Close to Zoo, U of L, Churchill Downs
Poplar Level
9.6 out of 10, Exceptional, (20)
"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 NZ$540
includes taxes & fees
4 Jan - 5 Jan
Private Home Close to Zoo, U of L, Churchill Downs

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)
"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 NZ$318
includes taxes & fees
2 Feb - 3 Feb
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

Beautiful restored Victorian farmhouse

Beautiful restored Victorian farmhouse
Shelbyville
9.4 out of 10, Exceptional, (13)
"Great location to downtown Shelbyville. Porch is awesome!!"
United States
Alison L.
The price is NZ$765
includes taxes & fees
5 Jan - 6 Jan
Beautiful restored Victorian farmhouse

Cozy KY Escape with Hot Tub near the Bourbon Trail

Cozy KY Escape with Hot Tub near the Bourbon Trail
Taylorsville
10.0 out of 10, Exceptional, (104)
"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 NZ$486
includes taxes & fees
4 Jan - 5 Jan
Cozy KY Escape with Hot Tub near the Bourbon Trail

Seabiscuit 5- Relax And Kick Back (Decorated for the 2025 Christmas Season)

Seabiscuit 5- Relax And Kick Back (Decorated for the 2025 Christmas Season)
Taylorsville
9.6 out of 10, Exceptional, (53)
"We had a girls weekend and everything was perfect. Would definitely stay here again."
United States
Susan N.
Seabiscuit 5- Relax And Kick Back (Decorated for the 2025 Christmas Season)

Angels Envy 29 - A relaxing place by the lake!

Angels Envy 29 - A relaxing place by the lake!
Taylorsville
9.4 out of 10, Exceptional, (20)
"Great place good accommodation "
United States
Ryan D.
The price is NZ$531
includes taxes & fees
4 Jan - 5 Jan
Angels Envy 29 - A relaxing place by the lake!

St. Matthews Retreat | Relaxing Home w/ Backyard!

St. Matthews Retreat | Relaxing Home w/ Backyard!
2.0 star property
Rockcreek Lexington Road
10.0 out of 10, Exceptional, (3)
"Fantastic service. The home was beautiful and if in town again we would definitely stay there again. Nice area great access to amenities. "
United States
T J.
The price is NZ$614
includes taxes & fees
5 Jan - 6 Jan
St. Matthews Retreat | Relaxing Home w/ Backyard!

Kentucky Sunrise 18- Greet the Sun As it Rises

Kentucky Sunrise 18- Greet the Sun As it Rises
Taylorsville
9.8 out of 10, Exceptional, (51)
"Quiet, peaceful place to rest. Perfect for a weekend getaway"
United States
Ryan D.
The price is NZ$610
includes taxes & fees
2 Feb - 3 Feb
Kentucky Sunrise 18- Greet the Sun As it Rises

Stylish Jeffersonville Home - Mins from Louisville

Stylish Jeffersonville Home - Mins from Louisville
Jeffersonville
9.0 out of 10, Wonderful, (20)
"This was a great place for us to stay for an event at the expedition center. Close to the highway for quick access to the city. "
United States
Chad L.
The price is NZ$551
includes taxes & fees
19 Jan - 20 Jan
Stylish Jeffersonville Home - Mins from Louisville

The Duke Hotel

The Duke Hotel
2.0 star property
Downtown Louisville
The price is NZ$288
includes taxes & fees
4 Jan - 5 Jan
The Duke Hotel

Cozy Cabin w/firepit, tucked in the woods on a Kentucky farm. Nature awaits!

Cozy Cabin w/firepit, tucked in the woods on a Kentucky farm. Nature awaits!
La Grange
10.0 out of 10, Exceptional, (38)
"Great place. Thanks!"
United States
Jonathan P.
The price is NZ$297
includes taxes & fees
7 Jan - 8 Jan
Cozy Cabin w/firepit, tucked in the woods on a Kentucky farm. Nature awaits!

Southern Family Charmer - Perfect Space & Location with style and comfort!

Southern Family Charmer - Perfect Space & Location with style and comfort!
Schnitzelburg
10.0 out of 10, Exceptional, (22)
"Good rooms and clean place"
United States
Mufid S.
The price is NZ$522
includes taxes & fees
4 Jan - 5 Jan
Southern Family Charmer - Perfect Space & Location with style and comfort!
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

Find out more about Simpsonville

Everything you need to know about Simpsonville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Simpsonville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Simpsonville holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Simpsonville holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Simpsonville. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Simpsonville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Simpsonville holiday rentals we have selected for you start as low as NZ$216 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Simpsonville rentals

At Expedia, we put the best Simpsonville holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Simpsonville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Simpsonville holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Simpsonville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.