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Our top choices for Simpsonville holiday rentals

9.8 out of 10, Exceptional, (8 reviews)
"The perfect location for a quick stop on the bourbon trail. Ten minutes from Bulleit, down the road from Jeptha Creed, and a short hop over to Buffalo Trace and downtown Louisville!"
United States
Shay D.
The price is £240
includes taxes & fees
4 Mar - 5 Mar
KY Bourbon Trail Home, King Bed, FirePit, Near Louisville
9.8 out of 10, Exceptional, (51 reviews)
"Quiet, peaceful place to rest. Perfect for a weekend getaway"
United States
Ryan D.
The price is £227
includes taxes & fees
2 Mar - 3 Mar
Kentucky Sunrise 18- Greet the Sun As it Rises
9.6 out of 10, Exceptional, (54 reviews)
"We had a girls weekend and everything was perfect. Would definitely stay here again."
United States
Susan N.
The price is £197
includes taxes & fees
2 Mar - 3 Mar
Seabiscuit 5- Relax And Kick Back (Decorated for the 2025 Christmas Season)
9.4 out of 10, Exceptional, (13 reviews)
"Great location to downtown Shelbyville. Porch is awesome!!"
United States
Alison L.
The price is £322
includes taxes & fees
2 Mar - 3 Mar
Beautiful restored Victorian farmhouse
10.0 out of 10, Exceptional, (11 reviews)
"Great place and centrally located if you are hitting the bourbon trail. "
United States
Eric B.
The price is £265
includes taxes & fees
3 Mar - 4 Mar
Bourbon Boating Lake House, 3bed, 3 bath cottage on Taylorsville Lake-Cottage 41
9.4 out of 10, Exceptional, (20 reviews)
"Just visited distilleries"
United States
Pam M.
The price is £224
includes taxes & fees
2 Mar - 3 Mar
Angels Envy 29 - A relaxing place by the lake!
10.0 out of 10, Exceptional, (72 reviews)
"The home was very clean, well stocked, and in a central location. We were extremely comfortable and found lots of things to do around town."
United States
Shannon W.
Germantown Fav! BOOK for Music Fests & DERBY 2026!
10.0 out of 10, Exceptional, (14 reviews)
"Clean and was as advertised Great location for our plans "
United States
Mike A.
The price is £112
includes taxes & fees
2 Mar - 3 Mar
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
10.0 out of 10, Exceptional, (31 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.
The price is £141
includes taxes & fees
24 Mar - 25 Mar
Unique Downtown Studio with an Industrial Vibe
9.6 out of 10, Exceptional, (24 reviews)
"This house was just as described. We had everything we needed and the property manager was awesome communicating the whole time. Would definitely recommend to anyone! "
United States
Renee C.
The price is £251
includes taxes & fees
2 Mar - 3 Mar
Private Home Close to Zoo, U of L, Churchill Downs

Aparthotel in Downtown Louisville

The Duke Hotel
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"Room was comfortable. "
United States
Mary
The price is £104
includes taxes & fees
2 Mar - 3 Mar
The Duke Hotel

Holiday Home in Camp Taylor

Close to Everything in Louisville!!!
9.4 out of 10, Exceptional, (37 reviews)
"This is a great little place to stay! Close to the Exposition Center and a lot of other attractions. It is an older place but clean and comfortable. This is our second stay at this place. "
United States
jaggers959
The price is £198
includes taxes & fees
2 Mar - 3 Mar
Close to Everything in Louisville!!!
10.0 out of 10, Exceptional, (105 reviews)
"Enjoyed the weekend"
United States
Peter F.
The price is £254
includes taxes & fees
2 Mar - 3 Mar
Cozy KY Escape with Hot Tub near the Bourbon Trail
10.0 out of 10, Exceptional, (25 reviews)
"Good rooms and clean place"
United States
Mufid S.
The price is £207
includes taxes & fees
2 Mar - 3 Mar
Southern Family Charmer - Perfect Space & Location with style and comfort!
8.8 out of 10, Excellent, (8 reviews)
"Stayed for a friends wedding at Whitehall. Location was great and we were able to walk to a handful of restaurants and coffee shops "
United States
Natalie H.
The price is £197
includes taxes & fees
4 Mar - 5 Mar
St. Matthew’s - Walk to Shops & Restaurants

Aparthotel in Tyler Park

The Bellwether Hotel
3.5 star property
8.8 out of 10, Excellent, (38 reviews)
"Clean room, history and location. "
United States
RICHARD
The price is £98
includes taxes & fees
2 Mar - 3 Mar
The Bellwether Hotel
10.0 out of 10, Exceptional, (53 reviews)
"We loved our stay at this cottage. Very quiet and relaxing. We will definitely stay here again!"
United States
Jarrod H.
The price is £180
includes taxes & fees
2 Mar - 3 Mar
Carriage House, 7 minutes from downtown Louisville
10.0 out of 10, Exceptional, (19 reviews)
"The Stables suite was perfect for an extended stay in Shelbyville. Great location and wonderful place to stay. "
United States
Kim K.
The price is £139
includes taxes & fees
2 Mar - 3 Mar
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
9.8 out of 10, Exceptional, (24 reviews)
"Very nice house, new hot tub in the resort it was located in was very nice"
United States
Mike O.
The price is £292
includes taxes & fees
2 Mar - 3 Mar
Ridge Retreat 42 Sleeps 8 + Crib. NEW HOT TUB

Holiday Home in Jeffersonville

Urban Explorer Pad | Near Downtown + Yard
9.0 out of 10, Wonderful, (41 reviews)
"Amazing stay, would stay again any time! Host was easy to communicate with and home was clean when we arrived and had everything needed for a wonderful stay!"
United States
Cameron J.
The price is £270
includes taxes & fees
2 Mar - 3 Mar
Urban Explorer Pad | Near Downtown + Yard
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 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, apart-hotels, 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 £98 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?

Spacious 4-bedroom townhome with 2 car garage in perfect Louisville location: This holiday home rental outside of Simpsonville offers a fireplace, a balcony 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 stovetop and a microwave, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a garden.

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.