Vacation rentals in Simpsonville

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Top-rated vacation rentals in Simpsonville

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Guest favorite

Train in Lawrenceburg

4.98 out of 5 average rating, 345 reviews

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of elm trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunk-beds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

Guest favorite

Home in Lawrenceburg

4.99 out of 5 average rating, 107 reviews

Cottage On Crooked Creek

A tranquil cottage nestled in the lush countryside and situated right along the Bourbon Trail, this completely renovated rare find is located center of Lawrenceburg, Frankfort and Shelbyville and only 12 min to I-64. With five main bourbon distilleries just 30 min, local wineries within a stone's throw, Churchill Downs and Keeneland Racecourse equidistant and Taylorsville Lake nearby there is little left to be desired when staying here. This is the perfect spot to relax with family and friends.

Guest favorite

Chalet in Lawrenceburg

4.95 out of 5 average rating, 176 reviews

Countryside On the Bourbon Trail, 22 Quiet Acres

Welcome to Sea Glass Farm. 1900's restored farmhouse with tons of charm! Full access to 22 acres with beautiful hilltop sunsets. In the heart of The Bourbon Trail, the scenery and wildlife will not disappoint. The location is perfect for a rural getaway or relaxing stop on your Bourbon Trail experience. Minutes from shopping and restaurants; situated between I-64 and The Bluegrass Parkway. This place has been a dream of ours and it will soon be in your dreams as well. Hosted by the owner!

Guest favorite

Cabin in Louisville

4.99 out of 5 average rating, 151 reviews

Historic Cabin by Bourbon Trail

Historic, unique, tasteful and serene - the Edward Tyler house, ca. 1783, is a stone cabin 20 minutes SE of Louisville on 13 acre estate. Near the famous bourbon trail, rental includes full cabin and large screen porch overlooking pond with fountain. First floor has living/dining/kitchen space with small sofa bed and stone fireplace (gas); queen bed and full bath on second floor. American and European antique furnishings and fine art welcome you to fully updated home with central HVAC.

Guest favorite

Barn in Mount Eden

4.99 out of 5 average rating, 143 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.

Guest favorite

Tiny home in La Grange

4.98 out of 5 average rating, 193 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

Guest favorite

Condo in Shelbyville

4.89 out of 5 average rating, 123 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!

Guest favorite

Cabin in Louisville

4.95 out of 5 average rating, 324 reviews

Captain's Cabin:Historic Romantic by Bourbon Trail

Your own log cabin on a wooded hillside 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.

Guest favorite

Guesthouse in Shelbyville

4.97 out of 5 average rating, 100 reviews

Cottage of Eden. Bourbon Trail Stay in Shelby Co.

Listen to the birds sing as the walkway guides you to your quaint cottage getaway. Take in nature, as you’re surrounded by trees, near our sweet chicken coop and a creek that flows down from the deck - all while only 10min from town. Special touches were added of Kentucky Derby photos, books, kitchenware, Bourbon Trail glasses and bourbon barrel heads with local distilleries. The dining table top is even made of wood from Shelby County’s own Bulleit Distilling Company.

Guest favorite

Home in Simpsonville

4.98 out of 5 average rating, 608 reviews

Private Lower Level King Bed/Patio

Guests access to the private finished walkout basement, fully fenced back yard. Near Bluegrass Outlet Mall & Louisville. An hour to Cincinnati & 45 to Lexington. King in the first bedroom, queen in second, sectional w/ reclining seats. Private patio/entry. Farm view, shopping, restaurants. Smoke-free! Homeowners live upstairs. Must be able to use stairs or walk a slight incline on the side yard. Cable offered on Smart TVs. Apps accessible. Fire pits.

Guest favorite

Cottage in Pleasureville

4.99 out of 5 average rating, 203 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.

Guest favorite

Dome in Mount Washington

4.98 out of 5 average rating, 119 reviews

My Old Kentucky Dome

An elevated camping “glamping” experience. This brand-new one of a kind geodesic dome is located on a private road that leads you to an overlook featuring one of the most beautiful countryside views in Kentucky. While this getaway experience is nestled deep in the woods, it is also a close drive to all the conveniences you can imagine. This is an off the grid outdoor experience with a ½ mile gravel road including a steep hill. AWD or 4WD advised.

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

Stay near Simpsonville's top sights

The Outlet Shoppes of the Bluegrass66 locals recommend

Bass Factory Outlet4 locals recommend

Brick+Mortar Boutique and Coffeehouse3 locals recommend

Other great vacation rentals in Simpsonville

Guest favorite

Guest suite in Shelbyville

4.98 out of 5 average rating, 58 reviews

Spacious suite, country views, pool table, firepit

Guest favorite

Guesthouse in Pendleton

4.97 out of 5 average rating, 90 reviews

The Wooded Retreat

Superhost

Home in Shelbyville

4.78 out of 5 average rating, 41 reviews

Pool*HOT TUB*Bourbon Trail

Superhost

Home in Shelbyville

4.89 out of 5 average rating, 9 reviews

Shelbyville, KY - Bourbon Trail and Horse Country.

Guest favorite

Home in Jeffersonville

4.98 out of 5 average rating, 66 reviews

Beachfront River Cottage

Guest favorite

Cabin in Louisville

5 out of 5 average rating, 58 reviews

Historically Registered 1847 Log Home

Guest favorite

Home in Shelbyville

5 out of 5 average rating, 18 reviews

~HOT TUB~Bourbon Trail~Ping Pong/Pool Table~Grill~

Guest favorite

Rental unit in Shelbyville

4.92 out of 5 average rating, 24 reviews

Bricks and Barrels

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Quick stats about vacation rentals in Simpsonville

Total rentals
10 properties
Nightly prices starting at
$80 before taxes and fees
Total number of reviews
850 reviews
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Local attractions
The Old Stone Inn & Tavern, Brick+Mortar Boutique and Coffeehouse, and The Lovely Fig

Vacation rentals in Simpsonville

Top-rated vacation rentals in Simpsonville

Train in Lawrenceburg

Home in Lawrenceburg

Chalet in Lawrenceburg

Cabin in Louisville

Barn in Mount Eden

Tiny home in La Grange

Condo in Shelbyville

Cabin in Louisville

Guesthouse in Shelbyville

Home in Simpsonville

Cottage in Pleasureville

Dome in Mount Washington

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Simpsonville vacation rentals

Stay near Simpsonville's top sights

Other great vacation rentals in Simpsonville

Guest suite in Shelbyville

Guesthouse in Pendleton

Home in Shelbyville

Home in Shelbyville

Home in Jeffersonville

Cabin in Louisville

Home in Shelbyville

Rental unit in Shelbyville

Quick stats about vacation rentals in Simpsonville

Total rentals

Nightly prices starting at

Total number of reviews

Wifi availability

Popular amenities

Local attractions

Destinations to explore