Holiday Rentals in Simpsonville

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Our top choices for Simpsonville holiday rentals

Quiet Downtown Maple Cottage Gem

Quiet Downtown Maple Cottage Gem
Shelbyville
10.0 out of 10, Exceptional, (1 review)
"Very convenient for Horse Show we were attending. Everything was as described and the hosts were very accommodating. "
United States
Marlena J.
The price is €293
includes taxes & fees
3 Jun - 4 Jun
Quiet Downtown Maple Cottage Gem

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 €161
includes taxes & fees
2 Jun - 3 Jun
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

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 €156
includes taxes & fees
3 Jun - 4 Jun
Unique Downtown Studio with an Industrial Vibe

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 €375
includes taxes & fees
1 Jun - 2 Jun
Beautiful restored Victorian farmhouse

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 €166
includes taxes & fees
1 Jun - 2 Jun
Whiskey Stop-Close to Ky Expo, Walkable & Parking!

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.
Bourbon Trail Retreat: Hot Tub & Game Room

Guests Love it! w/PrivPking-Bourbon, Music orWork!

Guests Love it! w/PrivPking-Bourbon, Music orWork!
Germantown
10.0 out of 10, Exceptional, (78 reviews)
"An excellent place to stay. Easy parking- excellent communication by the host and a quiet place to stay. The location was perfect in relation to what we wanted to see and do! "
United States
Jessica H.
The price is €185
includes taxes & fees
29 Jun - 30 Jun
Guests Love it! w/PrivPking-Bourbon, Music orWork!

Preston Retreat - Convenient Germantown Location

Preston Retreat - Convenient Germantown Location
Merriwether
8.2 out of 10, Very good, (13 reviews)
"Not sure what happened to the access code that didn't work and we had to contact the host for a new one. Otherwise, it was clean and the beds were comfy. Having two bathrooms was a plus. "
United States
Donald S.
The price is €175
includes taxes & fees
1 Jun - 2 Jun
Preston Retreat - Convenient Germantown Location

Close to Everything in Louisville!!!

Close to Everything in Louisville!!!
Camp Taylor
9.4 out of 10, Exceptional, (39 reviews)
"Everything about our stay was excellent."
United States
James H.
The price is €232
includes taxes & fees
1 Jun - 2 Jun
Close to Everything in Louisville!!!

The Bellwether Hotel

The Bellwether Hotel
3.5 star property
Tyler Park
9.0 out of 10, Wonderful, (49 reviews)
"Would stay again. Clean and comfortable in a great location. "
United States
David
The price is €142
includes taxes & fees
1 Jun - 2 Jun
The Bellwether Hotel

Historic stone cabin near Bourbon Trail on private 13 acre estate property!

Historic stone cabin near Bourbon Trail on private 13 acre estate property!
Louisville
10.0 out of 10, Exceptional, (20 reviews)
"Everything was outstanding!"
United States
John W.
The price is €267
includes taxes & fees
16 Jun - 17 Jun
Historic stone cabin near Bourbon Trail on private 13 acre estate property!

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 €381
includes taxes & fees
30 Jun - 1 Jul
St. Matthew’s - Walk to Shops & Restaurants

OG Highlands Home, Walkable & priv parking!

OG Highlands Home, Walkable & priv parking!
Germantown
10.0 out of 10, Exceptional, (61 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 €213
includes taxes & fees
1 Jun - 2 Jun
OG Highlands Home, Walkable & priv parking!

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 €127
includes taxes & fees
29 Jun - 30 Jun
Alfesco - Walkable Highlands Guesthouse

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)
"Clean and was as advertised Great location for our plans "
United States
Mike A.
The price is €138
includes taxes & fees
29 Jun - 30 Jun
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

Vintage yet Modern Highlands home! Walk to venues!

Vintage yet Modern Highlands home! Walk to venues!
Germantown
10.0 out of 10, Exceptional, (144 reviews)
"Great place to stay, would definitely recommend to anyone looking to stay in Louisville "
United States
Andy T.
The price is €178
includes taxes & fees
2 Jun - 3 Jun
Vintage yet Modern Highlands home! Walk to venues!

The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville

The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville
Louisville
10.0 out of 10, Exceptional, (203 reviews)
"Great location, nice property just as shown… awesome host will be back in the future. "
United States
Steve G.
The price is €281
includes taxes & fees
1 Jun - 2 Jun
The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville

Cozy Studio close to Music Hall, Food, & Shops!

Cozy Studio close to Music Hall, Food, & Shops!
Germantown
10.0 out of 10, Exceptional, (85 reviews)
"We really enjoyed our stay here. The place was clean and comfortable. "
Canada
Jonathon B.
The price is €147
includes taxes & fees
1 Jun - 2 Jun
Cozy Studio close to Music Hall, Food, & Shops!

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 €347
includes taxes & fees
1 Jun - 2 Jun
Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

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, (24 reviews)
"This home is warm and cozy and close to everything we had planned."
United States
Dawn G.
The price is €198
includes taxes & fees
1 Jun - 2 Jun
Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!
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, apart-hotels, 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 €142 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 9 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.