A brick clock tower with two clocks, surrounded by dense foliage.

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, (14 reviews)
"Great location to downtown Shelbyville. Porch is awesome!!"
United States
Alison L.
$389 nightly
The price is $433
Jun 30 - Jul 1
Total with taxes and fees
Beautiful restored Victorian farmhouse

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.
$316 nightly
The price is $351
Jul 5 - Jul 6
Total with taxes and fees
Quiet Downtown Maple Cottage Gem

Unique Downtown Studio with an Industrial Vibe

Unique Downtown Studio with an Industrial Vibe
Shelbyville
10.0 out of 10, Exceptional, (32 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.
$171 nightly
The price is $190
Jul 5 - Jul 6
Total with taxes and fees
Unique Downtown Studio with an Industrial Vibe

Preston Retreat - Convenient Germantown Location

Preston Retreat - Convenient Germantown Location
Merriwether
8.2 out of 10, Very Good, (13 reviews)
"Close to where we needed to be"
United States
terry k.
$196 nightly
The price is $199
Jun 30 - Jul 1
Total with taxes and fees
Preston Retreat - Convenient Germantown Location

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, (23 reviews)
"Awesome place, it was clean and spacious! "
United States
Ben M.
$452 nightly
The price is $512
Jun 30 - Jul 1
Total with taxes and fees
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill

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, (21 reviews)
"Everything was outstanding!"
United States
John W.
$238 nightly
The price is $276
Jun 30 - Jul 1
Total with taxes and fees
Historic stone cabin near Bourbon Trail on private 13 acre estate property!

Renovated 2BR/1BA Oasis in Jeffersonville - 10 Mins to Louisville - with Yard

Renovated 2BR/1BA Oasis in Jeffersonville - 10 Mins to Louisville - with Yard
Jeffersonville
10.0 out of 10, Exceptional, (6 reviews)
"Our stay was great. Beautiful house , very accommodating, everything we needed! Comfy and cozy and close to Big four bridge, would highly recommend "
United States
Sam T.
$205 nightly
The price is $231
Jul 5 - Jul 6
Total with taxes and fees
Renovated 2BR/1BA Oasis in Jeffersonville - 10 Mins to Louisville - with Yard

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, (20 reviews)
"The Stables suite was perfect for an extended stay in Shelbyville. Great location and wonderful place to stay. "
United States
Kim K.
$176 nightly
The price is $195
Jul 20 - Jul 21
Total with taxes and fees
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

Mid-Century Modern Gem Pet-Friendly 2BR w/ Deck

Mid-Century Modern Gem Pet-Friendly 2BR w/ Deck
Schnitzelburg
9.2 out of 10, Wonderful, (5 reviews)
"Nice place! "
United States
Sierra S.
$214 nightly
The price is $248
Jul 27 - Jul 28
Total with taxes and fees
Mid-Century Modern Gem Pet-Friendly 2BR w/ Deck

St. Matthew’s - Walk to Shops & Restaurants

St. Matthew’s - Walk to Shops & Restaurants
St. Matthews
9.0 out of 10, Wonderful, (12 reviews)
"We had everything we needed. Great location!"
United States
Adam S.
$348 nightly
The price is $404
Jun 30 - Jul 1
Total with taxes and fees
St. Matthew’s - Walk to Shops & Restaurants

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, (35 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.
$170 nightly
The price is $197
Jun 30 - Jul 1
Total with taxes and fees
Spacious Stylish Retreat in the Heart of Clifton Neighborhood, King Bed, Coffee!

Close to Everything in Louisville!!!

Close to Everything in Louisville!!!
Camp Taylor
9.4 out of 10, Exceptional, (40 reviews)
"Everything about our stay was excellent."
United States
James H.
$230 nightly
The price is $267
Jun 30 - Jul 1
Total with taxes and fees
Close to Everything in Louisville!!!

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, (25 reviews)
"Cool spot, great location. "
United States
Luke M.
$195 nightly
The price is $226
Jul 1 - Jul 2
Total with taxes and fees
Renovated 100-Year-Old Shotgun Home-- Modern Comfort Meets Local Character!

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, (148 reviews)
"Host were nice and friendly "
United States
Robert M.
$315 nightly
The price is $365
Jun 30 - Jul 1
Total with taxes and fees
Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

Alfesco - Walkable Highlands Guesthouse

Alfesco - Walkable Highlands Guesthouse
Deer Park
8.8 out of 10, Excellent, (12 reviews)
"Great communication, accommodations, and location- Trifecta! "
United States
Lisa K.
$124 nightly
The price is $143
Jul 6 - Jul 7
Total with taxes and fees
Alfesco - Walkable Highlands Guesthouse

The Bellwether Hotel

The Bellwether Hotel
3.5 star property
Tyler Park
9.0 out of 10, Wonderful, (51 reviews)
"Would stay again. Clean and comfortable in a great location. "
United States
David
$126 nightly
The price is $146
Jul 5 - Jul 6
Total with taxes and fees
The Bellwether Hotel

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, (23 reviews)
"Clean and was as advertised Great location for our plans "
United States
Mike A.
$144 nightly
The price is $163
Jul 6 - Jul 7
Total with taxes and fees
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

KING Sleep8 4Bed 2BR 2 BA Swepson Hideaway 202

KING Sleep8 4Bed 2BR 2 BA Swepson Hideaway 202
Shelby Park
10.0 out of 10, Exceptional, (4 reviews)
"Easy check in and clean!"
United States
Sally W.
$247 nightly
The price is $285
Jun 30 - Jul 1
Total with taxes and fees
KING Sleep8 4Bed 2BR 2 BA Swepson Hideaway 202

Kentucky Bourbon Trail Estate: Hot Tub & Game Room

Kentucky Bourbon Trail Estate: 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.
$509 nightly
The price is $565
Jul 14 - Jul 15
Total with taxes and fees
Kentucky Bourbon Trail Estate: Hot Tub & Game Room

✪Heated Pool, Firepit, Bikes, Grill, Pets✪

✪Heated Pool, Firepit, Bikes, Grill, Pets✪
Jeffersonville
8.4 out of 10, Very Good, (28 reviews)
"Unfortunately, we booked this house because of the pool and hot tub. We did not see in the fine print of the 60.00 per day to heat the pool. The hot tub has a grounding issue, so we were unable to use that either. The location was great to the KICC and the communication with the manager was great."
United States
Kimberly S.
$297 nightly
The price is $340
Jul 22 - Jul 23
Total with taxes and fees
✪Heated Pool, Firepit, Bikes, Grill, Pets✪
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 $146 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?

The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville: This vacation home rental outside of Simpsonville is located on a river and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the books in this rental home to help you unwind.

How many vacation rentals are there in Simpsonville?

Choose from 9 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.