Vacation rentals in Simpsonville

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Top-rated vacation rentals in Simpsonville

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Guest favorite

Cabin in Louisville

4.95 out of 5 average rating, 302 reviews

Captain's Cabin:Historic Romantic by Bourbon Trail

Your own log cabin on a wooded hillside overlooking a private lake with gourmet breakfast served to your door (on weekends)! It's been the location for Lifetime and Hallmark movies! Period furnishings and modern conveniences make this an unforgettable retreat. A massive stone fireplace creates a quiet ambiance. Watch wildlife from back porch swings. Comfy bed, luxury sheets, high-speed internet, bluetooth stereo and special touches make your stay magical! Ask for Cooking With Bourbon Experience

Jul 1 – 8

R5,068 ZAR per night

Guest favorite

Apartment in Simpsonville

4.98 out of 5 average rating, 130 reviews

Ridgecrest Estate. Comfort and convenience.

A newly renovated 650-sq-ft. upstairs apartment with private entrance. Property sits on 5 acres in the heart of the Saddlebred Capital of the world. Just 9 miles east of the Watterson Expressway, Ridgecrest estate is an ideal location for enjoying the best of Kentucky in a quiet and peaceful environment. Quick access to I-64 (1/4 mile); 45 min. to Keeneland, 30 min to Churchill Downs, and 2 min to the Outlet Shoppes. No children under 13. Additional guests more than 2, $20 extra per night.

Oct 8 – 15

R1,953 ZAR per night

Guest favorite

Guesthouse in Hardinsburg

4.96 out of 5 average rating, 179 reviews

Once Upon a Time little Cabin in the Woods

Welcome to Always Ranch where this unique tiny cabin offers you a tranquil spot to relax. You will be surrounded by nature and off the beaten path. The cabin may look like a lean to but the inside is rustic and warming. We are located 20 minutes form Salem, 20 minutes from Paoli and Paoli Peak, and 35 minutes from Frenchlick Casino The kitchenette includes mini fridge, microwave, double hot plate and, grill on the outdoor firepit or grill. Boats are NOT available for guests at this time

Mar 9 – 16

R2,197 ZAR per night

Guest favorite

Barn in Mount Eden

4.98 out of 5 average rating, 119 reviews

Sweet Hollow Farm

Sweet Hollow Farm is located near Taylorsville Lake. 30 miles from Louisville, 40 miles from Lexington and 25 from Bardstown. We have a small farm with a studio barn apartment. Private entrance with full bath. We also have a beautiful pool that we share with our guests. There is a horseshoe pit, fire pit and multiple outdoor seating areas. Kids and dogs are welcome. We even have space for horses and boats. We can offer peace and quiet, a clear view of the stars and hummingbird theatrics.

Jun 8 – 15

R2,424 ZAR per night

Guest favorite

Tiny home in La Grange

4.97 out of 5 average rating, 159 reviews

Brakeman's Cottage

"All Aboard the Brakeman's Cottage! Experience the charm of this tiny house listed on the National Register of Historic Buildings in LaGrange, Kentucky. Nestled just feet from the train tracks in the heart of downtown, it offers a unique experience. Situated across from the train observation tower and within walking distance of the best restaurants and quaint shops, our newly remodeled property features private off-street parking. Step into history with modern comforts at Brakeman's

Dec 3 – 10

R1,880 ZAR per night

Guest favorite

Condo in Shelbyville

4.89 out of 5 average rating, 109 reviews

Your Kentucky Home Away From Home

Lovely, renovated Patio Home features 2 bedrooms and 2 full baths – one with a low-entrance shower and one with a full tub. This Open Floor Plan has 1st Floor Entry, front-door parking and 36” doors, making it easily accessible. This home is fully furnished throughout, including a full kitchen with all appliances, dishes, drinkware and silverware, washer and dryer, wall-mounted flat-screen television, tasteful art, linens, towels and more. This is your home away from home!

Aug 19 – 26

R2,243 ZAR per night

Guest favorite

Guest suite in Prospect

4.97 out of 5 average rating, 169 reviews

Private Prospect Flat

Two bedroom apartment located on picturesque Covered Bridge Road in Prospect, KY. There is a separate entrance with plenty of parking. Beautiful views of Kentucky landscape from every window. Our property is four acres with a meandering stream, forest, and fields. There is a fully stocked kitchen including a dishwasher. The main bedroom includes a work space area and two closets. Feel free to grab a few eggs for breakfast if there are eggs in the nesting boxes.

Jun 19 – 26

R2,731 ZAR per night

Guest favorite

Cabin in Lawrenceburg

4.98 out of 5 average rating, 442 reviews

Bourbon Trail Cabin on the Farm

Recognized by AirBnB as the “2021 Top New AirBnB in the State of KY”!Overlooking rolling hay fields, and surrounded by wooded farm land, this cabin features barn wood walls, hardwood floors, handcrafted bourbon barrel sink, king bed, leather sleeper sofa, and custom built kitchenette. Located on a working cattle farm, see cows, goats, a donkey and horse, & our pet free-range pig! In the heart of the Bourbon Trail in the home of Wild Turkey and Four Roses.

Nov 12 – 19

R2,142 ZAR per night

Guest favorite

Cottage in Pleasureville

4.99 out of 5 average rating, 174 reviews

The Cozy Cottage on One Goat Farm

This quaint little cottage is located on the Bourbon Trail of Kentucky. A mere 9 minutes from Six-Mile Distillery, it is also in close proximity to a gas station, grocery and library. Located in the heart of an Amish community, you will hear horses and buggies clip-clopping past as you sip your morning coffee. This cottage is on a functioning farm with horses, cats, goats and donkeys, with overnight housing facilities for your own equines as well.

Jul 24 – 31

R2,086 ZAR per night

Guest favorite

Cabin in Mount Eden

4.97 out of 5 average rating, 107 reviews

Bourbon Country Cottage

Newly renovated cottage located in the country. Enjoy amazing views from the porch while enjoying the outdoor patio. Fully furnished to make your stay comfortable and delightful. Memory foam mattresses for wonderful sleep and a well equipped kitchen for cooking. Enjoy exploring the walking trails, creek and the 80 acre property while you stay. Stocked Fishing Pond Check out our other listing too, Bourbon Country Cabin, same property.

Jul 3 – 10

R2,958 ZAR per night

Guest favorite

Farm stay in Goshen

4.98 out of 5 average rating, 286 reviews

The Coop

This 2 bedroom house is a renovated old farmhouse located on the site of a small vegetable farm and native plant nursery. The back deck overlooks the woods, where you can watch the wild birds and keep an eye on the free range chickens. This is a quiet spot for a retreat, but also 25 minutes from downtown Louisville. The Coop has a fully stocked kitchen and comes with eggs right from our flock....

Nov 26 – Dec 3

R2,185 ZAR per night

Guest favorite

Farm stay in La Grange

4.95 out of 5 average rating, 625 reviews

The Cottage at StoneLedge 2 bedroom/1bath

Nestled on an expansive 80 acre horse farm, the cottage is the perfect escape. Hike the 30+ acres of woods that boast a creek and waterfall. Relax on the cozy front porch while enjoying the sounds of nature. If traveling with pets please note prior approval is required and be sure to read the pet policy in 'other things to note'. Thank you for your consideration.

Jan 6 – 13

R2,899 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Simpsonville vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Simpsonville

Guest favorite

Home in Simpsonville

4.94 out of 5 average rating, 64 reviews

Comfortable sleek home bourbon trail

Aug 20 – 27

R3,306 ZAR per night

Guest favorite

Farm stay in Simpsonville

4.85 out of 5 average rating, 62 reviews

Farm House - near Bourbon Trail & Pet Friendly

Aug 6 – 13

R2,664 ZAR per night

Guest favorite

Guest suite in Shelbyville

4.97 out of 5 average rating, 34 reviews

Spacious suite, country views, pool table, firepit

Feb 16 – 23

R2,479 ZAR per night

Guest favorite

Farm stay in Simpsonville

4.92 out of 5 average rating, 39 reviews

Spacious Getaway in the Country - 2 Bd, 2 1/2 Bath

Mar 19 – 26

R3,307 ZAR per night

Guest favorite

Guesthouse in Shelbyville

4.96 out of 5 average rating, 71 reviews

Cottage of Eden. Bourbon Trail Stay in Shelby Co.

Jun 19 – 26

R2,750 ZAR per night

Guest favorite

Guest suite in Shelbyville

5.0 out of 5 average rating, 61 reviews

Comfortable Charm on the Bourbon Trail & 2024 PGA

Jul 2 – 9

R3,059 ZAR per night

Guest favorite

Guest suite in Louisville

4.97 out of 5 average rating, 30 reviews

Middletown Private Guest House

Jun 16 – 23

R1,762 ZAR per night

Guest favorite

Apartment in Shelbyville

4.96 out of 5 average rating, 81 reviews

Unique Downtown Studio with an Industrial Vibe

Feb 7 – 14

R2,936 ZAR per night

Show all

Quick stats about vacation rentals in Simpsonville

Total rentals
10 properties
Local attractions
The Old Stone Inn & Tavern, Brick+Mortar Boutique and Coffeehouse, and The Lovely Fig
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
10 properties include access to wifi
Total number of reviews
800 reviews
Nightly prices starting at
R1,533 ZAR before taxes and fees

Vacation rentals in Simpsonville

Top-rated vacation rentals in Simpsonville

Cabin in Louisville

Apartment in Simpsonville

Guesthouse in Hardinsburg

Barn in Mount Eden

Tiny home in La Grange

Condo in Shelbyville

Guest suite in Prospect

Cabin in Lawrenceburg

Cottage in Pleasureville

Cabin in Mount Eden

Farm stay in Goshen

Farm stay in La Grange

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Simpsonville vacation rentals

Other great vacation rentals in Simpsonville

Home in Simpsonville

Farm stay in Simpsonville

Guest suite in Shelbyville

Farm stay in Simpsonville

Guesthouse in Shelbyville

Guest suite in Shelbyville

Guest suite in Louisville

Apartment in Shelbyville

Quick stats about vacation rentals in Simpsonville

Total rentals

Local attractions

Popular amenities

Wifi availability

Total number of reviews

Nightly prices starting at

Destinations to explore