Simpsonville Vacation Rentals

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Our top choices for Simpsonville vacation rentals

KY Bourbon Trail Home, King Bed, FirePit, Near Louisville

KY Bourbon Trail Home, King Bed, FirePit, Near Louisville
Shelbyville
9.8 out of 10, Exceptional, (8 reviews)
"The perfect location for a quick stop on the bourbon trail. Ten minutes from Bulleit, down the road from Jeptha Creed, and a short hop over to Buffalo Trace and downtown Louisville!"
United States
Shay D.
$314 nightly
The price is $349
Mar 24 - Mar 25
Total with taxes and fees
KY Bourbon Trail Home, King Bed, FirePit, Near Louisville

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 reviews)
"Quiet, peaceful place to rest. Perfect for a weekend getaway"
United States
Ryan D.
$283 nightly
The price is $311
Mar 24 - Mar 25
Total with taxes and fees
Kentucky Sunrise 18- Greet the Sun As it Rises

Seabiscuit 5- Relax And Kick Back

Seabiscuit 5- Relax And Kick Back
Taylorsville
9.6 out of 10, Exceptional, (54 reviews)
"We had a girls weekend and everything was perfect. Would definitely stay here again."
United States
Susan N.
$222 nightly
The price is $244
Mar 22 - Mar 23
Total with taxes and fees
Seabiscuit 5- Relax And Kick Back

Close to Everything in Louisville!!!

Close to Everything in Louisville!!!
Camp Taylor
9.4 out of 10, Exceptional, (37 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
$233 nightly
The price is $270
Mar 22 - Mar 23
Total with taxes and fees
Close to Everything in Louisville!!!

Springtime in Kentucky, Cabin, Sleeps 29, Visit Bourbon Trail, Ark and Nature

Springtime in Kentucky, Cabin, Sleeps 29, Visit Bourbon Trail, Ark and Nature
Bagdad
9.6 out of 10, Exceptional, (247 reviews)
"Great cabin for large families. "
United States
Anonymous traveler
$448 nightly
The price is $499
Mar 25 - Mar 26
Total with taxes and fees
Springtime in Kentucky, Cabin, Sleeps 29, Visit Bourbon Trail, Ark and Nature

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, (14 reviews)
"Clean and was as advertised Great location for our plans "
United States
Mike A.
$133 nightly
The price is $150
Mar 23 - Mar 24
Total with taxes and fees
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

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.
$396 nightly
The price is $440
Mar 23 - Mar 24
Total with taxes and fees
Beautiful restored Victorian farmhouse

Alfesco - Walkable Highlands Guesthouse

Alfesco - Walkable Highlands Guesthouse
Deer Park
8.6 out of 10, Excellent, (10 reviews)
"Great communication, accommodations, and location- Trifecta! "
United States
Lisa K.
$124 nightly
The price is $143
Mar 22 - Mar 23
Total with taxes and fees
Alfesco - Walkable Highlands Guesthouse

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, (106 reviews)
"The cottage is very clean and comfortable. I stayed with a friend and we were both impressed by how comfortable the beds are. The area the cottage is in is very pretty. I didn't stay long because I was in and out for a wedding, but I would definitely book this cottage again."
United States
Rachel I.
$316 nightly
The price is $348
Mar 22 - Mar 23
Total with taxes and fees
Cozy KY Escape with Hot Tub near the Bourbon Trail

Ridge Retreat 42 Sleeps 8 + Crib. NEW HOT TUB

Ridge Retreat 42 Sleeps 8 + Crib. NEW HOT TUB
Taylorsville
9.8 out of 10, Exceptional, (24 reviews)
"Very nice house, new hot tub in the resort it was located in was very nice"
United States
Mike O.
$365 nightly
The price is $402
Mar 22 - Mar 23
Total with taxes and fees
Ridge Retreat 42 Sleeps 8 + Crib. NEW HOT TUB

The Duke Hotel

The Duke Hotel
2.0 star property
Downtown Louisville
8.6 out of 10, Excellent, (8 reviews)
"Clean, lovely stay. "
United States
Hannah
$117 nightly
The price is $136
Mar 24 - Mar 25
Total with taxes and fees
The Duke Hotel

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 reviews)
"Just visited distilleries"
United States
Pam M.
$278 nightly
The price is $306
Mar 24 - Mar 25
Total with taxes and fees
Angels Envy 29 - A relaxing place by the lake!

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, (31 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.
$143 nightly
The price is $166
Mar 23 - Mar 24
Total with taxes and fees
Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee!

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, (143 reviews)
"Great Trip…We enjoyed the four (4) nights. Host was great and her Scones were a treat."
United States
Anonymous traveler
$347 nightly
The price is $403
Mar 22 - Mar 23
Total with taxes and fees
Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

The Bellwether Hotel

The Bellwether Hotel
3.5 star property
Tyler Park
8.8 out of 10, Excellent, (41 reviews)
"Clean room, history and location. "
United States
RICHARD
$112 nightly
The price is $131
Mar 29 - Mar 30
Total with taxes and fees
The Bellwether Hotel

St. Matthew’s - Walk to Shops & Restaurants

St. Matthew’s - Walk to Shops & Restaurants
St. Matthews
8.8 out of 10, Excellent, (8 reviews)
"It was everything we needed."
United States
Carmen C.
$229 nightly
The price is $265
Mar 30 - Mar 31
Total with taxes and fees
St. Matthew’s - Walk to Shops & Restaurants

Cozy Riverside Apt. Min to Downtown Louisville. King Bed, Coffee Bar!

Cozy Riverside Apt. Min to Downtown Louisville. King Bed, Coffee Bar!
Jeffersonville
9.8 out of 10, Exceptional, (31 reviews)
"Host was welcoming and gave great ideas of things to do. Nice cozy apartment, would stay again. "
United States
Angela M.
$115 nightly
The price is $130
Mar 24 - Mar 25
Total with taxes and fees
Cozy Riverside Apt. Min to Downtown Louisville. King Bed, Coffee Bar!

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

+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+
Jeffersonville
9.4 out of 10, Exceptional, (85 reviews)
"Great host beautiful house "
United States
Shantej G.
$292 nightly
The price is $334
Mar 22 - Mar 23
Total with taxes and fees
+Derby Home-HOT TUB, Barrel Sauna, Firepit, PETS+

Carriage House, 7 minutes from downtown Louisville

Carriage House, 7 minutes from downtown Louisville
louisville
10.0 out of 10, Exceptional, (56 reviews)
"We loved our stay at this cottage. Very quiet and relaxing. We will definitely stay here again!"
United States
Jarrod H.
$209 nightly
The price is $243
Mar 24 - Mar 25
Total with taxes and fees
Carriage House, 7 minutes from downtown Louisville

Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill

Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill
Crescent Hill
10.0 out of 10, Exceptional, (119 reviews)
"Host met onsite, informed of details and was friendly and helpful. Good location and nicely remodeled older home w lots of updates. Would stay again. "
United States
Dale K.
$204 nightly
The price is $237
Mar 22 - Mar 23
Total with taxes and fees
Quiet, Cozy & Safe 2 Bed 1 Bath in Crescent Hill
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 $131 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?

Spacious 4-bedroom townhome with 2 car garage in perfect Louisville location: This vacation home rental outside of Simpsonville offers a fireplace, a balcony, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a garden.

How many vacation rentals are there in Simpsonville?

Choose from 8 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 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 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.