Holiday rentals with outdoor seating in Shelbyville

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

Top-rated Holiday Houses with Outdoor Seating in Shelbyville

Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

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Guest favourite

Home in Lawrenceburg

4.99 out of 5 average rating, 108 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 favourite

Cabin in Frankfort

5 out of 5 average rating, 111 reviews

On The Rocks

Ultimate in privacy, yet two minutes from downtown Frankfort! This cabin-style home (think Gatlinburg!) sits on three wooded acres. Long, rambling decks on three sides (one covered, one fully screened, one open air). Our adjacent farm surrounds the property, making it even more private. This home sits high on a bluff above downtown Frankfort & the Kentucky River (our farm borders on the river). Just three miles to Buffalo Trace Distillery (if you could fly, it's way closer than that!)

Guest favourite

Chalet in Lawrenceburg

4.96 out of 5 average rating, 178 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 favourite

Cabin in Louisville

4.99 out of 5 average rating, 154 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.

Superhost

Home in Shelbyville

4.8 out of 5 average rating, 140 reviews

Parris on Main

Parris on Main Street is the perfect location to enjoy the historic town of Shelbyville and, a few blocks walking distance to many antique shops, local coffee houses and great locations to grab a bite to eat. **Update - brand new ac system installed 7/19/2023 Newly renovated, built in 1942, this house is perfect for a family or group of friends wanting to experience the wonderful places Kentucky has to offer. Right in the middle the Bourbon Trail and about 30 minutes from ChurchIll Downs

Guest favourite

Condo in Shelbyville

4.91 out of 5 average rating, 112 reviews

Kentucky bourbon, horses, cozy condo

Welcome to your home away from home! Great place to stay while visiting local establishments, horse shows, bourbon trail, extended work stay or family. Work or Play this adorable condo was recently renovated and has all the comforts of home! King bed in main bedroom with full bath, queen size guest bed and 2nd large bathroom, wifi, fully furnished kitchen along with washer and dryer. Parking at your entrance with no steps! Just minutes from I64, groceries, restaurants and shopping!

Guest favourite

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 favourite

Tiny home in La Grange

4.98 out of 5 average rating, 194 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 favourite

Guesthouse in Shelbyville

4.97 out of 5 average rating, 101 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 favourite

Cabin in Lawrenceburg

4.98 out of 5 average rating, 513 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.

Guest favourite

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 favourite

Dome in Mount Washington

4.98 out of 5 average rating, 122 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.