Simpsonville Vacation Rentals

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Our top choices for Simpsonville vacation rentals

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.
$187 nightly
The price is $208
May 26 - May 27
Total with taxes and fees
Unique Downtown Studio with an Industrial Vibe

Quiet Downtown Maple Cottage Gem

Quiet Downtown Maple Cottage Gem
Shelbyville
$316 nightly
The price is $351
May 10 - May 11
Total with taxes and fees
Quiet Downtown Maple Cottage Gem

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.
$351 nightly
The price is $407
May 25 - May 26
Total with taxes and fees
St. Matthew’s - Walk to Shops & Restaurants

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 11 - May 12
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 10 - May 11
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 10 - May 11
Total with taxes and fees
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

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 27 - May 28
Total with taxes and fees
Alfesco - Walkable Highlands Guesthouse

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.
$163 nightly
The price is $189
May 10 - May 11
Total with taxes and fees
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.
$198 nightly
The price is $229
May 11 - May 12
Total with taxes and fees
Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!

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 13 - May 14
Total with taxes and fees
Historic stone cabin near Bourbon Trail on private 13 acre estate property!

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, (17 reviews)
"House was cozy, and host was responsive. Rooms were clean and welcoming. A lovely place to stay."
United States
Alec S.
$145 nightly
The price is $164
Jun 2 - Jun 3
Total with taxes and fees
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

Perfect Kentucky Derby stay near Churchill Downs!

Perfect Kentucky Derby stay near Churchill Downs!
Jeffersonville
$230 nightly
The price is $246
May 10 - May 11
Total with taxes and fees
Perfect Kentucky Derby stay near Churchill Downs!

Close to Everything in Louisville!!!

Close to Everything in Louisville!!!
Camp Taylor
9.4 out of 10, Exceptional, (38 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 10 - May 11
Total with taxes and fees
Close to Everything in Louisville!!!

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

+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+
Jeffersonville
9.4 out of 10, Exceptional, (88 reviews)
"Very nice place"
United States
Seth B.
$309 nightly
The price is $353
May 13 - May 14
Total with taxes and fees
+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+

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.
$346 nightly
The price is $402
May 18 - May 19
Total with taxes and fees
Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

Secretariat Twin Spires Suite!

Secretariat Twin Spires Suite!
Jeffersonville
8.8 out of 10, Excellent, (5 reviews)
"Very nice, clean, great location."
United States
Leigh
$140 nightly
The price is $143
May 26 - May 27
Total with taxes and fees
Secretariat Twin Spires Suite!

The Adelyn, where comfort meets convenience

The Adelyn, where comfort meets convenience
Jeffersonville
10.0 out of 10, Exceptional, (8 reviews)
"The host was super responsive. The place was absolutely a gem!"
United States
Jeffery
$274 nightly
The price is $310
May 12 - May 13
Total with taxes and fees
The Adelyn, where comfort meets convenience

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.
$485 nightly
The price is $550
May 17 - May 18
Total with taxes and fees
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill

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.
$209 nightly
The price is $243
May 10 - May 11
Total with taxes and fees
Carriage House, 7 minutes from downtown Louisville

Stylish House Walking Distance from the Fun of the Highlands!

Stylish House Walking Distance from the Fun of the Highlands!
Phoenix Hill
9.4 out of 10, Exceptional, (32 reviews)
"We will stay here over and over again. It’s a lovely place that a perfect location."
United States
Jennifer H.
$163 nightly
The price is $189
May 13 - May 14
Total with taxes and fees
Stylish House Walking Distance from the Fun of the Highlands!
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 $149 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.