Simpsonville Holiday Rentals

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Holiday Rentals in Simpsonville

Hancock House

3.0 star property
8.0 out of 10, Very good, (198)
"I was impressed with the room. It smelled nice, it was clean, and I really liked the design. They programmed a set of codes for me and they were easy to follow. I also felt like the parking was safe. I would definitely stay there again. "
The price is AU$253
includes taxes & fees
6 Jan - 7 Jan
Hancock House

Stellar Suites

4.5 star property
9.6 out of 10, Exceptional, (89)
"Outstanding!"
The price is AU$334
includes taxes & fees
17 Jan - 18 Jan
Stellar Suites

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

9.6 out of 10, Exceptional, (212)
"Great cabin in close proximity to several distilleries. Communication with the owner was excellent. She answered all our questions very quickly. The cabin was clean and decorated for Christmas, which our family loved. We enjoyed the trails and my son found that their pond does have 5lb largemouth bass. Know that if you go with multiple families or large groups, you'll most likely be sharing some bedrooms. We were aware of this ahead of time and didn't bother us. Only thing keeping the cabin from...
The price is AU$862
includes taxes & fees
5 Jan - 6 Jan
Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin, Sleeps 29!

22-acre Home on Bourbon Trail w/ Sunroom!

3.0 star property
22-acre Home on Bourbon Trail w/ Sunroom!

The Bellwether Hotel

2.0 star property
7.6 out of 10, Good, (9)
"Beautifully redone historic building. Enjoyed design features and Christmas decor! Great walkable neighborhood. "
The price is AU$226
includes taxes & fees
26 Jan - 27 Jan
The Bellwether Hotel

Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail

10.0 out of 10, Exceptional, (199)
"The property was clean and just as the pictures showed. Jeramie was a wonderful host and talked us through the process of getting the fireplace started through a late night phone call. Would definitely stay there again."
Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail

4 rooms for rent

The price is AU$228
includes taxes & fees
15 Jan - 16 Jan
4 rooms for rent

Cheerful Historical Mansion 8-bedrooms and 6 baths Vacation Home in Derby City

9.8 out of 10, Exceptional, (61)
"Really enjoyed the house, very spacious. Great host as well, would recommend staying here!"
The price is AU$2,049
includes taxes & fees
14 Jan - 15 Jan
Cheerful Historical Mansion 8-bedrooms and 6 baths Vacation Home in Derby City

River City Retreat near Zoo/Expo/Airport/Churchill + Arcade

9.8 out of 10, Exceptional, (50)
"Close to the Expo for the livestock show stay. House was clean. Beds were comfortably. "
River City Retreat near Zoo/Expo/Airport/Churchill + Arcade

★ Victorian Louisville ★ Large 1200 sqft APT #1

9.8 out of 10, Exceptional, (139)
"Gorgeous hard wood floors, comfortable beds, and relaxing atmosphere! Hosts responded quickly to any questions. Easy parking! "
The price is AU$312
includes taxes & fees
6 Jan - 7 Jan
★ Victorian Louisville ★ Large 1200 sqft APT #1

Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!

10.0 out of 10, Exceptional, (81)
"The host of this property is great. She communicates well and was easily accessible. The property is clean and in a great location if you are looking for things south of Louisville. Great layout for families with kids and in-laws. "
The price is AU$722
includes taxes & fees
6 Jan - 7 Jan
Close to Bourbon Trail/Parks/Easy access to I-65/Pool/Firepit/Free Firewood!

Cozy Cabin w/firepit, tucked in the woods on a Kentucky farm. Nature awaits!

10.0 out of 10, Exceptional, (32)
"Loved the stay,the cabin and the area. Will definitely be back"
The price is AU$306
includes taxes & fees
31 Jan - 1 Feb
Cozy Cabin w/firepit, tucked in the woods on a Kentucky farm. Nature awaits!

Close to Everything in Louisville!!!

9.4 out of 10, Exceptional, (28)
"Very clean and nice place close to the exposition center would stay there again."
The price is AU$384
includes taxes & fees
15 Jan - 16 Jan
Close to Everything in Louisville!!!

☆Stunning Derby Home☆ 5 KING BEDS, HOT TUB,FIREPIT

9.0 out of 10, Wonderful, (20)
"Wonderful set up for our ladies weekend. Tyler was easy to work with and very responsive. Jeffersonville is a hidden gem!"
The price is AU$601
includes taxes & fees
6 Jan - 7 Jan
☆Stunning Derby Home☆ 5 KING BEDS, HOT TUB,FIREPIT

Chic Rustic Loft minutes from Downtown! Short walk to Lynn Stadium and Breweries

10.0 out of 10, Exceptional, (45)
"Loved the space and only minutes from downtown. "
The price is AU$228
includes taxes & fees
6 Jan - 7 Jan
Chic Rustic Loft minutes from Downtown! Short walk to Lynn Stadium and Breweries

6BD - Riverfront Home w/ Gorgeous Views

9.2 out of 10, Wonderful, (23)
"We had a wonderful time in this home. Easy to rent and everything we needed! "
The price is AU$1,094
includes taxes & fees
15 Jan - 16 Jan
6BD - Riverfront Home w/ Gorgeous Views

The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville

10.0 out of 10, Exceptional, (173)
"Just what we needed to get away just the two of us. Would love to come back in the summer and stay again. Close to everything we needed. "
The River's Edge Oasis...Relax & unwind...Casual luxury close to downtown Lville

The Waterfall Suite Place + Walkout! Both Overlook Waterfall!

9.8 out of 10, Exceptional, (39)
"It is great for large families and perfect for families with children under age 12. Lots for them to do."
The Waterfall Suite Place + Walkout! Both Overlook Waterfall!

Captain's Cabin Bed & Breakfast: Historic & Romantic

9.8 out of 10, Exceptional, (127)
"Had a great weekend at Captain's cabin. we immediately started a fire in the fireplace and enjoyed the quiet popping and warmth of the fire all weekend. Tammy's breakfasts are outstanding. Found some fun things to do in town when we finally pealed ourselves from the cabin."
The price is AU$677
includes taxes & fees
15 Jan - 16 Jan
Captain's Cabin Bed & Breakfast: Historic & Romantic

The Orange Door ~ Prime Germantown 4BR/2BA Luxury

10.0 out of 10, Exceptional, (19)
"It was pretty solid no real complaints."
The price is AU$646
includes taxes & fees
7 Jan - 8 Jan
The Orange Door ~ Prime Germantown 4BR/2BA Luxury
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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Other types of properties in Simpsonville you may be interested in

Hampton Inn Simpsonville

2.5 star property
9.4 out of 10, Exceptional, (757)
"Always nice and clean and very nice people"
The price is AU$166
includes taxes & fees
9 Jan - 10 Jan
Hampton Inn Simpsonville

Crowne Plaza Louisville Airport Expo Ctr, an IHG Hotel

3.5 star property
8.6 out of 10, Excellent, (258)
"Very nice "
The price is AU$166
includes taxes & fees
5 Jan - 6 Jan
Crowne Plaza Louisville Airport Expo Ctr, an IHG Hotel

Derby City Gaming & Hotel - A Churchill Downs Property

4.0 star property
9.4 out of 10, Exceptional, (923)
"This place was amazing! One of the cleanest hotels we have ever stayed in! Highly recommended to everyone!"
The price is AU$207
includes taxes & fees
5 Jan - 6 Jan
Derby City Gaming & Hotel - A Churchill Downs Property
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.

Frequently asked questions

Can I find a holiday rental in Simpsonville?

Yes, there are holiday rentals close to the most popular sights in Simpsonville, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Simpsonville has to offer?

Cheerful Historical Mansion 8-bedrooms and 6 baths Vacation Home in Derby City: This holiday home rental outside of Simpsonville is located on a river, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Simpsonville?

Choose from 8 Expedia holiday rentals in Simpsonville for a memorable holiday.

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 E.P. Tom Sawyer State 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 holiday rental in Simpsonville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Simpsonville. Holiday rentals offer extras like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for family trips or small group gatherings.