Simpsonville Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Simpsonville vacation rentals

TV, fireplace
Sleeps 26, Hot Tub, Sauna, Privacy on 5 acres

Sleeps 26, Hot Tub, Sauna, Privacy on 5 acres

2.0 star property
Simpsonville
Sleeps 26, Hot Tub, Sauna, Privacy on 5 acres
Highland Station Penthouse Suite | Private kitchen | Microwave, coffee/tea maker, paper towels
The Bellwether Hotel

The Bellwether Hotel

3.5 star property
Tyler Park
8.8 out of 10, Excellent, (32)
"Spectacular room, fabulous decor, tasty cookies, quiet stay "
United States
Mark
The price is ￥16,667
￥19,347 total
includes taxes & fees
Jan 10 - Jan 11, 2026
The Bellwether Hotel
Signature Suite, 1 Queen Bed, Non Smoking | Premium bedding, down comforters, memory foam beds
Stellar Suites

Stellar Suites

4.5 star property
Downtown Louisville
9.6 out of 10, Exceptional, (117)
"Clean and great location "
United States
Greg
The price is ￥16,728
￥27,555 total
includes taxes & fees
Dec 25 - Dec 26
Stellar Suites
Executive Room | View from room
Hancock House

Hancock House

3.0 star property
Downtown Louisville
8.2 out of 10, Very Good, (246)
"Worked great for our family. Would stay again. "
United States
Manda
Hancock House
Full-size fridge, microwave, oven, stovetop
The Duke Hotel

The Duke Hotel

2.0 star property
Downtown Louisville
The price is ￥15,190
￥25,421 total
includes taxes & fees
Dec 14 - Dec 15
The Duke Hotel
Interior
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!

Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!

Louisville
9.8 out of 10, Exceptional, (76)
"Interesting property!"
United States
Donald R.
The price is ￥98,007
￥191,693 total
includes taxes & fees
Dec 11 - Dec 12
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!
Exterior
Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin, Sleeps 29!

Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin, Sleeps 29!

Bagdad
9.6 out of 10, Exceptional, (240)
"Great place to stay, quiet, beautiful scenery and plenty of games and things to do. "
United States
Leah G.
Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin, Sleeps 29!
Seasonal outdoor pool
CozySuites at Nulu

CozySuites at Nulu

4.0 star property
Downtown Louisville
8.2 out of 10, Very Good, (26)
"The unit was clean, all communications were timely, the property has all the amenities, and NULU is very walkable. A perfect stay! My only regret is that I wasn't able to extend the stay. Highly recommended if you're in the Louisville area "
United States
William
The price is ￥9,815
￥31,284 total
includes taxes & fees
Dec 11 - Dec 12
CozySuites at Nulu
Outdoor spa tub
Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!

Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!

Jeffersontown
9.6 out of 10, Exceptional, (25)
"Great place good time "
United States
Jefferey S.
The price is ￥55,944
￥115,565 total
includes taxes & fees
Dec 11 - Dec 12
Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!
Outdoor spa tub
Spectacular waterfront house!

Spectacular waterfront house!

Prospect
9.6 out of 10, Exceptional, (86)
"Great location with views of the river. "
United States
Patrick G.
Spectacular waterfront house!
Exterior detail
Close to Everything in Louisville!!!

Close to Everything in Louisville!!!

Camp Taylor
9.4 out of 10, Exceptional, (37)
"Matches the description and photos "
United States
Angela C.
The price is ￥14,898
￥40,046 total
includes taxes & fees
Dec 15 - Dec 16
Close to Everything in Louisville!!!
Exterior
Secluded Hilltop Luxury Retreat-Bourbon Trail-Taylorsville Lake-Pool & Hot Tub

Secluded Hilltop Luxury Retreat-Bourbon Trail-Taylorsville Lake-Pool & Hot Tub

Bloomfield
10.0 out of 10, Exceptional, (1)
"All I can say is wow!!!! This house was amazing. If you are looking for a space to get away and relax with the family/friends this is the place hands down. Located in the heart of bourbon country, and close to bourbon tours all around. this house offers great escape from the hustle and bustle of the city and has many features and amenities, about a 50 min from Louisville and Lexington. I’m not giving 5 stars because that’s all it would let me do… I would give 10 stars if I could. Our family...
United States
Rick P.
The price is ￥59,823
￥147,011 total
includes taxes & fees
Dec 17 - Dec 18
Secluded Hilltop Luxury Retreat-Bourbon Trail-Taylorsville Lake-Pool & Hot Tub
Fridge, microwave, oven, stovetop
Preston Retreat - Convenient Germantown Location

Preston Retreat - Convenient Germantown Location

Merriwether
5.0 out of 10, (4)
"Worked out well for our metro adventure. Older house with charm. Really does but up to the park which is great for walking and meeting the super nice neighbors. "
United States
Cory G.
The price is ￥9,971
￥34,146 total
includes taxes & fees
Dec 14 - Dec 15
Preston Retreat - Convenient Germantown Location
House | Private kitchen | Fridge, microwave, oven, stovetop
Newly renovated 4BR CozySuites

Newly renovated 4BR CozySuites

4.0 star property
Smoketown Jackson
10.0 out of 10, Exceptional, (1)
"Excellent "
United States
Naguib
Newly renovated 4BR CozySuites
Property grounds
Steps to Restaurants, Nightlife, Shops- PacMan/King Bed/Bardstown Rd/Highlands

Steps to Restaurants, Nightlife, Shops- PacMan/King Bed/Bardstown Rd/Highlands

Louisville
10.0 out of 10, Exceptional, (10)
"My family of four (boys 9 and 11) were in town for a week to visit family. Great stay, clean place, wonderfully helpful and responsive owner. "
United States
Matthew B.
The price is ￥12,619
￥41,049 total
includes taxes & fees
Dec 11 - Dec 12
Steps to Restaurants, Nightlife, Shops- PacMan/King Bed/Bardstown Rd/Highlands
Property grounds
The Highlands Hideaway, 50 steps from Restaurant Row, Downtown, Expo, Highlands

The Highlands Hideaway, 50 steps from Restaurant Row, Downtown, Expo, Highlands

Deer Park
10.0 out of 10, Exceptional, (165)
"Great place to stay on our vacation to Louisville. "
United States
Melissa M.
The price is ￥27,263
￥65,277 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Highlands Hideaway, 50 steps from Restaurant Row, Downtown, Expo, Highlands
Terrace/patio
Charming home in the heart of the city!

Charming home in the heart of the city!

Irish Hill
10.0 out of 10, Exceptional, (14)
"The house had a lot of nice little touches that really pushed into the 5 star range for me. Great coffee selection, lots of bourbon glasses, great TV room, plenty of linens and towels, and even a nice little backyard hangout spot (even though we didn’t have time to use it). Really great find in terms of location as well. It’s within walk of plenty of bars, breakfast, and dinner spots."
United States
Nathan C.
Charming home in the heart of the city!
5 bedrooms, iron/ironing board, free WiFi, bed sheets
Cabin+Bunkhouse Sleeps 23 near Lex Lou Like New Spacious Modern Rustic Retreat

Cabin+Bunkhouse Sleeps 23 near Lex Lou Like New Spacious Modern Rustic Retreat

Shelbyville
10.0 out of 10, Exceptional, (3)
"Great place to stay. Highly recommend"
United States
Jackson D.
The price is ￥98,655
￥200,215 total
includes taxes & fees
Dec 16 - Dec 17
Cabin+Bunkhouse Sleeps 23 near Lex Lou Like New Spacious Modern Rustic Retreat
2 bedrooms, iron/ironing board, WiFi, bed sheets
Huge 2-bedroom apartment with 500 Mbps WiFi, full kitchen, AC/Heat, and sleeps 7

Huge 2-bedroom apartment with 500 Mbps WiFi, full kitchen, AC/Heat, and sleeps 7

Butchertown
10.0 out of 10, Exceptional, (8)
"lt was a great overall! David was communicative, the place was very clean, and the location was perfect."
United States
Anthony C.
Huge 2-bedroom apartment with 500 Mbps WiFi, full kitchen, AC/Heat, and sleeps 7
Fridge, microwave, stovetop, dishwasher
The Gallery Loft - Walk & Dine!

The Gallery Loft - Walk & Dine!

Clifton
9.8 out of 10, Exceptional, (59)
"Comfortable stay!"
United States
Akshansh G.
The Gallery Loft - Walk & Dine!
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

Hawthorn Suites by Wyndham Louisville East

Hawthorn Suites by Wyndham Louisville East

10/10 Excellent
"Room was impressive, especially for that price range. Room was impeccable and the furniture looked new. Only complaint I have was the exercise room where the machines weren't working. "
Napoleon 1-night trip
Posted 1 day ago
Hawthorn Suites by Wyndham Louisville East

Find out more about Simpsonville

Search for holiday rentals in Simpsonville on Expedia! You can easily find your home rentals, villas, holiday apartments in Simpsonville using one of the methods below:

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Look no further and take a look at our great range of rental properties in Simpsonville!

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?

Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!: 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. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

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.