Simpsonville Holiday Rentals

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Holiday Rentals in Simpsonville

Pool
Pool. HotTub. Bourbon Trail. Churchill Downs. Keeneland. Outlet Mall. KY Derby.
Pool. HotTub. Bourbon Trail. Churchill Downs. Keeneland. Outlet Mall. KY Derby.
Front of property
Stellar Suites
4.5 star property
9.6 out of 10, Exceptional, (68)
"I have enjoyed my stays at Stellar Suites. "
The price is NZ$292
includes taxes & fees
16 Jun - 17 Jun
Stellar Suites
Interior
Kentucky House: 22-acre Property on Bourbon Trail
3.0 star property
Kentucky House: 22-acre Property on Bourbon Trail
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Traditional Studio | Living area
Hancock House
3.0 star property
7.8 out of 10, Good, (164)
"The room was beautiful!! The staff responded almost immediately when texted, and were extremely helpful. Overall the stay was amazing!! Would definitely stay again. "
The price is NZ$284
includes taxes & fees
10 Jun - 11 Jun
Hancock House
Premium Suite | Private kitchen
The Bellwether Hotel
2.5 star property
7.4 out of 10, Good, (3)
"I drove around for an hour waiting for a parking space to become available close to the hotel. There was no one on site at 7 pm when I arrived, and my code for the outside door would not work. Luckily, two guests let me in when they went in. The room had one little window at the top of the corner, making it feel like I was in the basement. The furnishings were cheap, and the floor was concrete. NOT cozy or inviting at all."
The price is NZ$404
includes taxes & fees
29 May - 30 May
The Bellwether Hotel
Living area
One room rent
The price is NZ$226
includes taxes & fees
3 Jun - 4 Jun
One room rent
Property grounds
Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail
10.0 out of 10, Exceptional, (178)
"A+++"
Lakeside Cottage - upgraded hot tub! - near KY Bourbon Trail
Fridge, microwave, oven, stovetop
Cheerful Historical Mansion 8-bedrooms and 6 baths Vacation Home in Derby City
9.8 out of 10, Exceptional, (53)
"My group of 8 had an excellent time time at the house. There were ample beds for all to have their own private room and many additional beds to spare. The space is a wonderful historical mansion, with clearly several additions over the years. The outdoor spaces are sensational! Great destination for a big group!"
The price is NZ$2,158
includes taxes & fees
29 May - 30 May
Cheerful Historical Mansion 8-bedrooms and 6 baths Vacation Home in Derby City
Exterior
Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin
9.8 out of 10, Exceptional, (187)
"We had gathered friends and family from around the country to play some golf and attend the PGA Championship at Valhalla. The cabin was everything Mary said it was. It was clean and had enough beds and space for our party of 12. It was quiet, had plenty of pots, pans and glasses. Everything worked. The pool table was great. We recommend this property for a large group"
The price is NZ$1,083
includes taxes & fees
5 Jun - 6 Jun
Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin
Exterior
Close to Everything in Louisville!!!
9.4 out of 10, Exceptional, (25)
"Great"
The price is NZ$398
includes taxes & fees
29 May - 30 May
Close to Everything in Louisville!!!
Exterior
Captain's Cabin Bed & Breakfast: Historic & Romantic
10.0 out of 10, Exceptional, (113)
"Beautiful, well maintained cottage. We loved it! We wished we could have stayed longer. Very close to local activities and the airport."
The price is NZ$639
includes taxes & fees
4 Jun - 5 Jun
Captain's Cabin Bed & Breakfast: Historic & Romantic
Property grounds
Cozy Cabin w/firepit, tucked in the woods on a Kentucky farm. Nature awaits!
10.0 out of 10, Exceptional, (21)
"Our only regret was not spending more time here. We arrived late, after dark, and left early, before sunrise. The property is awesome and the star gazing was great."
The price is NZ$276
includes taxes & fees
4 Jun - 5 Jun
Cozy Cabin w/firepit, tucked in the woods on a Kentucky farm. Nature awaits!
Outdoor dining
6BD - Riverfront Home w/ Gorgeous Views
9.0 out of 10, Wonderful, (17)
"Our family goes to the National Farm Machinery Show and Tractor Pulls every year. We have stayed 2 years in this house on the river, it has a beautiful view, the house is very nice and host very easy to work with."
The price is NZ$964
includes taxes & fees
17 Jun - 18 Jun
6BD - Riverfront Home w/ Gorgeous Views
Fridge, microwave, oven, stovetop
★ Victorian Louisville ★ Large 1200 sqft APT #1
9.8 out of 10, Exceptional, (115)
"Accurate listing, good location and clean and spacious house that is great value for the money"
The price is NZ$313
includes taxes & fees
30 May - 31 May
★ Victorian Louisville ★ Large 1200 sqft APT #1
Property grounds
GET AWAY FROM IT ALL - Cottage 28 Taylorsville Lake
9.4 out of 10, Exceptional, (22)
"Yearly my wife and I get away just to enjoy our time together. This is the second year in a row we stayed at this location and we are planning on next year already. The cabin is so relaxing and the host is outstanding in communicating with us before our arrival. This is the place to be. Thank you for an enjoyable time."
GET AWAY FROM IT ALL - Cottage 28 Taylorsville Lake
Property grounds
Family/Pet-Friendly Riverside Home w/Amazing Views
9.8 out of 10, Exceptional, (11)
"Great view"
Family/Pet-Friendly Riverside Home w/Amazing Views
Fridge, microwave, oven, stovetop
Cozy Bourbon Speakeasy Themed Loft - Minutes from Downtown!
9.8 out of 10, Exceptional, (23)
"The place was very nice and clean. Would definitely stay again"
The price is NZ$284
includes taxes & fees
4 Jun - 5 Jun
Cozy Bourbon Speakeasy Themed Loft - Minutes from Downtown!
Exterior
The Waterfall Suite Place + Walkout! Both Overlook Waterfall!
9.8 out of 10, Exceptional, (36)
"We've joined together for Thanksgiving for several years and this was by far the nicest place. My only complaint would be the ice maker didn't work. We hope to visit again!"
The Waterfall Suite Place + Walkout! Both Overlook Waterfall!
Smart TV, books
Chic Rustic Loft minutes from Downtown! Short walk to Lynn Stadium and Breweries
9.8 out of 10, Exceptional, (28)
"This was exactly as pictured- so cozy and so close to town. It was a great place to stay with a few friends!"
The price is NZ$228
includes taxes & fees
29 May - 30 May
Chic Rustic Loft minutes from Downtown! Short walk to Lynn Stadium and Breweries
Fridge, microwave, oven, stovetop
Walk Everywhere !Downtown With A View
8.4 out of 10, Very good, (23)
"We had friends in for pre-wedding events, and it was a great location to travel back and forth from Louisville. We also enjoyed the decor in the home and the space was more than enough for our group."
The price is NZ$360
includes taxes & fees
29 May - 30 May
Walk Everywhere !Downtown With A View
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See all available properties in Simpsonville
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.

Other types of properties in Simpsonville you may be interested in

Standard Room, 2 Queen Beds, Non Smoking
Microtel Inn by Wyndham Louisville East
2.0 star property
7.0 out of 10, Good, (1015)
"I have stayed there many times and as always the staff was excellent they are always nice and friendly and willing to help"
The price is NZ$109
includes taxes & fees
12 Jun - 13 Jun
Microtel Inn by Wyndham Louisville East
Interior
Crowne Plaza Louisville Airport Expo Center, an IHG Hotel
3.5 star property
7.6 out of 10, Good, (1007)
"Greeted warmly by the checkin staff "
The price is NZ$198
includes taxes & fees
3 Jun - 4 Jun
Crowne Plaza Louisville Airport Expo Center, an IHG Hotel
Restaurant
Hotel Genevieve
4.0 star property
9.2 out of 10, Wonderful, (300)
"Our stay was more comfortable because Andrew Finney listened and helped make the experience better than it would otherwise be. Thank you. "
The price is NZ$383
includes taxes & fees
9 Jun - 10 Jun
Hotel Genevieve
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Simpsonville holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Simpsonville. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Simpsonville. Seeing all the best attractions is bound to make you fall in love with Simpsonville. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Simpsonville short-term rentals, that won’t be hard to do.

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.

How many holiday rentals are there in Simpsonville?

Choose from 7 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 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 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.

Recent reviews of Simpsonville properties
Expedia verified reviews