Simpsonville Holiday Rentals

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Our top choices for Simpsonville holiday rentals

Beautiful restored Victorian farmhouse

Beautiful restored Victorian farmhouse
Shelbyville
9.4 out of 10, Exceptional, (14 reviews)
"Great location to downtown Shelbyville. Porch is awesome!!"
United States
Alison L.
The price is NZ$749
includes taxes & fees
25 May - 26 May
Beautiful restored Victorian farmhouse

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 NZ$304
includes taxes & fees
26 May - 27 May
Unique Downtown Studio with an Industrial Vibe

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 NZ$312
includes taxes & fees
24 May - 25 May
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

Top Floor Apt Near Churchill Downs & Expo Center

Top Floor Apt Near Churchill Downs & Expo Center
Audubon
10.0 out of 10, Exceptional, (4 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 NZ$277
includes taxes & fees
25 May - 26 May
Top Floor Apt Near Churchill Downs & Expo Center

Quiet Downtown Maple Cottage Gem

Quiet Downtown Maple Cottage Gem
Shelbyville
The price is NZ$580
includes taxes & fees
24 May - 25 May
Quiet Downtown Maple Cottage Gem

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 NZ$1,083
includes taxes & fees
8 June - 9 June
Bourbon Trail Retreat: Hot Tub & Game Room

Cozy Kentucky Derby stay close to Churchill Downs!

Cozy Kentucky Derby stay close to Churchill Downs!
Jeffersonville
The price is NZ$419
includes taxes & fees
24 May - 25 May
Cozy Kentucky Derby stay close to Churchill Downs!

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 NZ$331
includes taxes & fees
26 May - 27 May
Whiskey Stop-Close to Ky Expo, Walkable & Parking!

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 NZ$698
includes taxes & fees
30 May - 31 May
St. Matthew’s - Walk to Shops & Restaurants

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 NZ$244
includes taxes & fees
25 May - 26 May
Alfesco - Walkable Highlands Guesthouse

A Derby getaway – only minutes to Churchill Downs!

A Derby getaway – only minutes to Churchill Downs!
Paristown Pointe
10.0 out of 10, Exceptional, (12 reviews)
"Great place!"
United States
Nakoma F.
The price is NZ$412
includes taxes & fees
25 May - 26 May
A Derby getaway – only minutes to Churchill Downs!

Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill

Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill
Frankfort
9.8 out of 10, Exceptional, (20 reviews)
"Beautiful home and surroundings!"
United States
Peg H.
The price is NZ$942
includes taxes & fees
24 May - 25 May
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill

The Burnt Barrel | New HotTub & Grill | Backyard!

The Burnt Barrel | New HotTub & Grill | Backyard!
Germantown
10.0 out of 10, Exceptional, (4 reviews)
"This property is simply wonderful. The atmosphere is super nice and cozy, and the area is super quiet. I had an amazing night, and the weather was perfect for a dip in the hot tub . I definitely recommend it, and I am sure I will return to this beautiful property."
Mexico
Juan Miguel
The price is NZ$459
includes taxes & fees
8 June - 9 June
The Burnt Barrel | New HotTub & Grill | Backyard!

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 NZ$460
includes taxes & fees
25 May - 26 May
Close to Everything in Louisville!!!

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 NZ$273
includes taxes & fees
22 June - 23 June
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

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 NZ$326
includes taxes & fees
25 May - 26 May
Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee!

Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!

Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!
Shelby Park
9.6 out of 10, Exceptional, (23 reviews)
"This home is warm and cozy and close to everything we had planned."
United States
Dawn G.
The price is NZ$384
includes taxes & fees
2 June - 3 June
Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!

The Bellwether Hotel

The Bellwether Hotel
3.5 star property
Tyler Park
9.0 out of 10, Wonderful, (49 reviews)
"Unique and beautiful hotel in a great area. Would highly recommend."
United States
Erika
The price is NZ$265
includes taxes & fees
8 June - 9 June
The Bellwether Hotel

Feelin Good- 2Bdrm/2Ba in Germantown w/Parking!

Feelin Good- 2Bdrm/2Ba in Germantown w/Parking!
Germantown
10.0 out of 10, Exceptional, (23 reviews)
"The place was very clean and in a great location."
United States
Paul S.
The price is NZ$489
includes taxes & fees
25 May - 26 May
Feelin Good- 2Bdrm/2Ba in Germantown w/Parking!

Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance
Louisville
9.8 out of 10, Exceptional, (147 reviews)
"Very nice couple , will stay there again"
United States
Bryan S.
The price is NZ$681
includes taxes & fees
25 May - 26 May
Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance
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$265 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?

Newly renovated 4BR CozySuites: This holiday home rental outside of 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.