Holiday Rentals in Simpsonville

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Our top choices for Simpsonville holiday rentals

The Bellwether Hotel

The Bellwether Hotel
3.5 star property
Tyler Park
9.0 out of 10, Wonderful, (44 reviews)
"Clean room, history and location. "
United States
RICHARD
The price is €143
includes taxes & fees
17 May - 18 May
The Bellwether Hotel

LUX Farmhouse on Bourbon Trail! Hot tub, Game Room, Firepit, Yard Games, 5-Acres

LUX Farmhouse on Bourbon Trail! Hot tub, Game Room, Firepit, Yard Games, 5-Acres
Bagdad
9.6 out of 10, Exceptional, (11 reviews)
"I had my bachelor party here and it was the perfect place to get away!"
United States
Kyser M.
The price is €1,037
includes taxes & fees
30 Apr - 1 May
LUX Farmhouse on Bourbon Trail! Hot tub, Game Room, Firepit, Yard Games, 5-Acres

SALE! Hot Tub Oasis: Bourbon Trail + Pets Welcome

SALE! Hot Tub Oasis: Bourbon Trail + Pets Welcome
Bagdad
10.0 out of 10, Exceptional, (22 reviews)
"We enjoyed our stay. It's a great cozy and comfortable place that's secluded and private. Iris was a great host. "
United States
Madison W.
The price is €489
includes taxes & fees
21 Apr - 22 Apr
SALE! Hot Tub Oasis: Bourbon Trail + Pets Welcome

Springtime in Kentucky, Cabin, Sleeps 29, Visit Bourbon Trail, Ark and Nature

Springtime in Kentucky, Cabin, Sleeps 29, Visit Bourbon Trail, Ark and Nature
Bagdad
9.6 out of 10, Exceptional, (250 reviews)
"Great cabin for large families. "
United States
Anonymous traveller
The price is €511
includes taxes & fees
21 Apr - 22 Apr
Springtime in Kentucky, Cabin, Sleeps 29, Visit Bourbon Trail, Ark and Nature

Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance
Louisville
9.8 out of 10, Exceptional, (143 reviews)
"Great Trip…We enjoyed the four (4) nights. Host was great and her Scones were a treat."
United States
Anonymous traveller
The price is €342
includes taxes & fees
19 Apr - 20 Apr
Captain's Cabin Bed & Breakfast: Bourbon Trail, History & Romance

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, (31 reviews)
"Stay was great"
United States
Jake T.
The price is €626
includes taxes & fees
17 Apr - 18 Apr
Safe, Comfortable, Clean & Convenient! - Make your stay memorable & Book Now!

Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill

Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill
Frankfort
10.0 out of 10, Exceptional, (19 reviews)
"Beautiful home and surroundings!"
United States
Peg H.
The price is €472
includes taxes & fees
17 May - 18 May
Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill

Seabiscuit 5- Relax And Kick Back

Seabiscuit 5- Relax And Kick Back
Taylorsville
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 €250
includes taxes & fees
19 Apr - 20 Apr
Seabiscuit 5- Relax And Kick Back

Beautiful restored Victorian farmhouse

Beautiful restored Victorian farmhouse
Shelbyville
9.4 out of 10, Exceptional, (13 reviews)
"Great location to downtown Shelbyville. Porch is awesome!!"
United States
Alison L.
The price is €373
includes taxes & fees
30 Apr - 1 May
Beautiful restored Victorian farmhouse

Luxury farmhouse on Bourbon Trail with hot tub - Bulleit 4 mi - Frankfort 15 mi

Luxury farmhouse on Bourbon Trail with hot tub - Bulleit 4 mi - Frankfort 15 mi
Bagdad
10.0 out of 10, Exceptional, (16 reviews)
"Great location and very clean. Plenty of room to spread out and relax. Carrie is a Professional and thoughtful host!!"
United States
David S.
Luxury farmhouse on Bourbon Trail with hot tub - Bulleit 4 mi - Frankfort 15 mi

Historic Cottage with modern amenities

Historic Cottage with modern amenities
louisville
9.4 out of 10, Exceptional, (27 reviews)
"Perfect place for our short stay in Louisville! Very nice neighborhood and cozy cottage! "
United States
Adrienne H.
The price is €332
includes taxes & fees
17 Apr - 18 Apr
Historic Cottage with modern amenities

Historic stone cabin near Bourbon Trail on private 13 acre estate property!

Historic stone cabin near Bourbon Trail on private 13 acre estate property!
Louisville
10.0 out of 10, Exceptional, (19 reviews)
"Everything was outstanding!"
United States
John W.
The price is €239
includes taxes & fees
19 Apr - 20 Apr
Historic stone cabin near Bourbon Trail on private 13 acre estate property!

Angels Envy 29 - A relaxing place by the lake!

Angels Envy 29 - A relaxing place by the lake!
Taylorsville
9.4 out of 10, Exceptional, (20 reviews)
"Just visited distilleries"
United States
Pam M.
The price is €260
includes taxes & fees
19 Apr - 20 Apr
Angels Envy 29 - A relaxing place by the lake!

Close to Everything in Louisville!!!

Close to Everything in Louisville!!!
Camp Taylor
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 €230
includes taxes & fees
19 Apr - 20 Apr
Close to Everything in Louisville!!!

Alfesco - Walkable Highlands Guesthouse

Alfesco - Walkable Highlands Guesthouse
Deer Park
8.6 out of 10, Excellent, (10 reviews)
"Great communication, accommodations, and location- Trifecta! "
United States
Lisa K.
The price is €125
includes taxes & fees
20 Apr - 21 Apr
Alfesco - Walkable Highlands Guesthouse

The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade Barn, Sleeps 12+

The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade Barn, Sleeps 12+
Shelbyville
9.6 out of 10, Exceptional, (5 reviews)
"We stayed at the Rec Farm for a short family stay for new years 2026. The cabin is cute, the long drive way into the property is nice, the cabin sits back away from the main street. I have 2 teen boys that enjoyed the Rec building; although it is not connected to the main house and it was below freezing all weekend. Inside, the cabin was ok; it was a smaller than I expected from viewing the pictures, but enough room for our family with 3 bedrooms. One of the bedroom windows did not stay...
United States
Norma M.
The price is €596
includes taxes & fees
20 Apr - 21 Apr
The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade Barn, Sleeps 12+

Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi
Shelbyville
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 €159
includes taxes & fees
19 Apr - 20 Apr
Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

Unique Downtown Studio with an Industrial Vibe

Unique Downtown Studio with an Industrial Vibe
Shelbyville
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 €154
includes taxes & fees
20 Apr - 21 Apr
Unique Downtown Studio with an Industrial Vibe

Luxury lodge in the heart of the Bluegrass

Luxury lodge in the heart of the Bluegrass
Waddy
10.0 out of 10, Exceptional, (9 reviews)
"Great property, nice location, well appointed. It is close to the interstate and with the leaves off, truck traffic could be heard from the top floor master bed. We would stay here again."
United States
Anonymous traveller
The price is €1,791
includes taxes & fees
19 Apr - 20 Apr
Luxury lodge in the heart of the Bluegrass

Close to Ky Fairgrounds&Expo, Churchill Downs!

Close to Ky Fairgrounds&Expo, Churchill Downs!
Germantown
10.0 out of 10, Exceptional, (75 reviews)
"The amenities were great and the house was the perfect spot for our weekend getaway. "
United States
Janessa D.
The price is €290
includes taxes & fees
24 Apr - 25 Apr
Close to Ky Fairgrounds&Expo, Churchill Downs!
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 €143 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 is equipped with a garden, air conditioning and WiFi to help you feel comfortable during your stay. 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 9 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.