Simpsonville Vacation Rentals

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Our top choices for Simpsonville vacation rentals

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.
$401 nightly
The price is $446
May 18 - May 19
Total with taxes and fees
Beautiful restored Victorian farmhouse

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.
$554 nightly
The price is $615
May 17 - May 18
Total with taxes and fees
Bourbon Trail Retreat: Hot Tub & Game Room

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.
$165 nightly
The price is $183
May 18 - May 19
Total with taxes and fees
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

Quiet Downtown Maple Cottage Gem

Quiet Downtown Maple Cottage Gem
Shelbyville
$314 nightly
The price is $349
May 17 - May 18
Total with taxes and fees
Quiet Downtown Maple Cottage Gem

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
$232 nightly
The price is $269
May 17 - May 18
Total with taxes and fees
Close to Everything in Louisville!!!

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.
$168 nightly
The price is $195
May 18 - May 19
Total with taxes and fees
Whiskey Stop-Close to Ky Expo, Walkable & Parking!

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.
$500 nightly
The price is $556
May 17 - May 18
Total with taxes and fees
LUX Farmhouse on Bourbon Trail! Hot tub, Game Room, Firepit, Yard Games, 5-Acres

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.
$186 nightly
The price is $207
May 20 - May 21
Total with taxes and fees
Unique Downtown Studio with an Industrial Vibe

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.
$207 nightly
The price is $240
May 16 - May 17
Total with taxes and fees
Carriage House, 7 minutes from downtown Louisville

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, (144 reviews)
"Very nice couple , will stay there again"
United States
Bryan S.
$345 nightly
The price is $400
May 18 - May 19
Total with taxes and fees
Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

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.
$354 nightly
The price is $411
May 31 - Jun 1
Total with taxes and fees
St. Matthew’s - Walk to Shops & Restaurants

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

Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill
Frankfort
10.0 out of 10, Exceptional, (19 reviews)
"Beautiful home and surroundings!"
United States
Peg H.
$442 nightly
The price is $501
May 17 - May 18
Total with taxes and fees
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill

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.
$198 nightly
The price is $229
May 17 - May 18
Total with taxes and fees
Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!

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.
$144 nightly
The price is $163
Jun 8 - Jun 9
Total with taxes and fees
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

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.
$241 nightly
The price is $280
May 19 - May 20
Total with taxes and fees
Historic stone cabin near Bourbon Trail on private 13 acre estate property!

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.
$124 nightly
The price is $143
May 18 - May 19
Total with taxes and fees
Alfesco - Walkable Highlands Guesthouse

Cozy Kentucky Derby stay close to Churchill Downs!

Cozy Kentucky Derby stay close to Churchill Downs!
Jeffersonville
$242 nightly
The price is $258
May 17 - May 18
Total with taxes and fees
Cozy Kentucky Derby stay close to Churchill Downs!

+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+

+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+
Jeffersonville
9.4 out of 10, Exceptional, (89 reviews)
"Very nice place"
United States
Seth B.
$287 nightly
The price is $328
May 19 - May 20
Total with taxes and fees
+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+

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.
$145 nightly
The price is $168
May 18 - May 19
Total with taxes and fees
Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee!

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
$152 nightly
The price is $163
May 17 - May 18
Total with taxes and fees
Top Floor Apt Near Churchill Downs & Expo Center
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Simpsonville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Simpsonville vacation 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 low season months. For more hustle and bustle, you may prefer to visit Simpsonville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $147 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Simpsonville rentals

At Expedia, we put the best Simpsonville vacation 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 vacation.

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 vacation rental in Simpsonville?

Yes, you can find vacation rentals near the most popular local attractions in Simpsonville, or you can go with a secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals in Simpsonville?

Newly renovated 4BR CozySuites: This vacation 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 you can cook with friends or family.

How many vacation rentals are there in Simpsonville?

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

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 vacation rental in Simpsonville like?

A vacation rental is a private property you can book for a few weeks or just a few days in Simpsonville. Vacation rentals feature extras such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a family trip.