Simpsonville Holiday Rentals

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Holiday Rentals in Simpsonville

Stellar Suites

4.5 star property
9.6 out of 10, Exceptional, (104)
"Great spot a must stay"
The price is NZ$298
includes taxes & fees
29 Sept - 30 Sept
Stellar Suites

InTown Suites Extended Stay Louisville KY - Preston Hwy

3.0 star property
7.0 out of 10, Good, (16)
"Staff has been great "
InTown Suites Extended Stay Louisville KY - Preston Hwy

Hancock House

3.0 star property
8.2 out of 10, Very good, (241)
"Worked great for our family. Would stay again. "
Hancock House

The Bellwether Hotel

2.0 star property
8.2 out of 10, Very good, (17)
"The boutique Bellwether Hotel is so beautiful and a step back in time. The art deco design, the second floor lounge, and the rooms all beautifully decorated and comfortable. Walk to restaurants, grocery, bars and antique shops. "
The price is NZ$229
includes taxes & fees
9 Sept - 10 Sept
The Bellwether Hotel

Newly renovated 4BR CozySuites

4.0 star property
10.0 out of 10, Exceptional, (1)
"Excellent "
Newly renovated 4BR CozySuites

CozySuites at Nulu

4.0 star property
8.2 out of 10, Very good, (21)
"Wonderful stay - great spot and lots of great dining options and bars nearby "
The price is NZ$321
includes taxes & fees
8 Sept - 9 Sept
CozySuites at Nulu

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

9.8 out of 10, Exceptional, (70)
"This place was a perfect stay for my bachelor party! There was a ton of room, the host was very responsive with any questions and it had everything we needed. Highly recommend! "
The price is NZ$2,088
includes taxes & fees
1 Sept - 2 Sept
Cheerful 8-Bedroom, 6-Bath Historic Mansion in Derby City – Ideal Vacation Home!

Stay on Broadway - Sleeps 10, Hot Tub, Walkable!

8.8 out of 10, Excellent, (8)
"Visit to celebrate my wife’s commencement, we all enjoyed our stay very much"
Stay on Broadway - Sleeps 10, Hot Tub, Walkable!

Wanderlust - Hot tub / fire pit - Location!

9.8 out of 10, Exceptional, (7)
"4 guys in our group. We all had big comfy beds and enjoyed the hot tub and fire pit outside. Would recommend!"
Wanderlust - Hot tub / fire pit - Location!

Close to Everything in Louisville!!!

9.4 out of 10, Exceptional, (33)
"House provided a clean environment and space for three adults and two small dogs. It was central location to get to other stops in Louisville. Enclosed back yard provided spot for dogs. Neighbors were nice. Everything we needed was provided. "
The price is NZ$483
includes taxes & fees
2 Sept - 3 Sept
Close to Everything in Louisville!!!

Bourbon Country Cabin with HOT TUB and Fire Pit on Brashears Creek

9.8 out of 10, Exceptional, (34)
"A rustic cabin situated in a quiet rural setting with all the essentials provided for a restful getaway. Clean and well maintained, with a super simple check-in process. "
Bourbon Country Cabin with HOT TUB and Fire Pit on Brashears Creek

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

9.6 out of 10, Exceptional, (229)
"The place was awesome and suited the bachelor party perfectly!"
Bourbon Trail, Ark Encounter, Family Gatherings, WiFi, Cabin, Sleeps 29!

4 rooms for rent

2.0 out of 10, (1)
"We ended up not staying due to not being able to get a hold of the host. Also called vrbo and they couldnt contact the host"
The price is NZ$236
includes taxes & fees
1 Sept - 2 Sept
4 rooms for rent

Bourbon Trail Retreat 5 King Beds Sleeps 18 Gated Private Family-Friendly

10.0 out of 10, Exceptional, (2)
"This post will be long. My family and I were completely surprised by the beauty of this property. The intentionality of the bedrooms, interior decorations, the size of the property , so we all could stretch out. I am thoroughly impressed. We will be back."
Bourbon Trail Retreat 5 King Beds Sleeps 18 Gated Private Family-Friendly

Gallant Fox - NuLu/Downtown

10.0 out of 10, Exceptional, (23)
"This was a beautiful place and close to great restaurants downtown. Would definitely recommend!"
The price is NZ$1,008
includes taxes & fees
25 Sept - 26 Sept
Gallant Fox - NuLu/Downtown

Large Private Home close to Bourbon Trail!/POOL/Free Firewood/Parks/Close to I65

10.0 out of 10, Exceptional, (93)
"Everything from top to bottom was fantastic about this property. The location was perfectly located to be able to go into Louisville or Bardstown. "
Large Private Home close to Bourbon Trail!/POOL/Free Firewood/Parks/Close to I65

Spectacular waterfront house!

9.6 out of 10, Exceptional, (78)
"We had a great time and loved the view of the river! "
Spectacular waterfront house!

Cozy Tree-Lined Carriage Home - Stay in Serenity!

9.6 out of 10, Exceptional, (14)
"We absolutely loved staying here while in town visiting family. This place is spacious and beautifully decorated with lots of amenities. We would definitely stay here again. "
The price is NZ$281
includes taxes & fees
3 Sept - 4 Sept
Cozy Tree-Lined Carriage Home - Stay in Serenity!

Louisville's Best Area, Walk to All!

9.8 out of 10, Exceptional, (177)
"A beautiful, well maintained and clean home. The owners were responsive, friendly and helpful. I would absolutely stay here again."
Louisville's Best Area, Walk to All!

NEW Distiller's Dream - Country House and Bar-n- 12 min to Downtown Bardstown

10.0 out of 10, Exceptional, (2)
"Host provided great communication before and after our stay. Super great location for anyone visiting the Bourbon Trail. Thank you for making our stay in Kentucky such a great experience for everyone!"
The price is NZ$1,182
includes taxes & fees
29 Sept - 30 Sept
NEW Distiller's Dream - Country House and Bar-n- 12 min to Downtown Bardstown
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

Find out more about Simpsonville

Everything you need to know about Simpsonville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Simpsonville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Simpsonville holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Simpsonville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Simpsonville holiday rentals we have selected for you start as low as NZ$229 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Simpsonville rentals

At Expedia, we put the best Simpsonville holiday 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 holiday.

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 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?

Newly renovated 4BR CozySuites: This holiday home rental outside Simpsonville offers a garden, a BBQ 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 fridge and a stovetop, so that you can cook with friends or family.

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 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.