Holiday rentals in Shelby County

5 out of 5 average rating, 80 reviews

Cabin in Frankfort

Bourbon Trail Cabin!~hot tub~hiking~game shed!

Experience a luxurious KY retreat at this unique & peaceful log cabin! This newly & thoughtfully renovated space is made with YOU, the guest, in mind! Perfect for those wanting to explore the 🥃Bourbon Trail🥃 or other nearby tourist attractions, While still featuring plentiful amenities on site, such as: - A hot tub - Private 1/4 mile hiking trail - Game shed - Fire pit - Covered porch - Wooded picnic area And more! Luxury is just a peaceful, countryside drive away at the Kentucky Bourbon Den!

4.98 out of 5 average rating, 142 reviews

Home in Lawrenceburg

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 suite in Shelbyville

5 out of 5 average rating, 95 reviews

Comfortable Charm on the Bourbon Trail

You’ll be charmed by this adorable place to stay, close to the interstate, making travel to Valhalla Golf Course, bourbon distilleries, Churchill Downs, and other attractions in nearby Louisville a breeze. We are in a beautiful rural setting, just right for relaxing. Our space has its own private entrance with a comfortable living room and private bathroom downstairs, and features a loft with queen bed and desk. There are a microwave, coffee maker, and fridge available for your convenience.

4.96 out of 5 average rating, 204 reviews

Chalet in Lawrenceburg

Countryside On the Bourbon Trail, 22 Quiet Acres

Welcome to Sea Glass Farm. 1900's restored farmhouse with tons of charm! 22 acres of privacy. Cows may be present in pasture. 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 we look forward to sharing it with you. Hosted by the owners.

4.91 out of 5 average rating, 123 reviews

Apartment in Shelbyville

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 house in Shelbyville

4.97 out of 5 average rating, 112 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.

5 out of 5 average rating, 24 reviews

Loft in Shelbyville

The Lucky Penny Downtown Loft - Central Location!

Experience timeless charm in this beautifully renovated mid-19th century Airbnb in the heart of Shelbyville. With soaring 14 ft ceilings, this historic gem combines classic architecture with modern amenities. Centrally located, it offers convenient access to local attractions, dining, and shopping. Enjoy a blend of elegance and comfort in a space that honors its rich heritage while providing all the contemporary conveniences you need for a memorable stay.

4.98 out of 5 average rating, 106 reviews

Loft in Shelbyville

LeCoop Loft close to all the popular distilleries

Ultra Luxury downtown 2 BR loft, spacious enough for 5 adults. Located in quaint Downtown Shelbyville, KY, you are in the heart of the bluegrass near major distilleries and race tracks and close to coffee shops, restaurants and bars right on the same block. You can't go wrong with this unique loft for its decor and proximity to everything. Close to all distilleries on the eastern part of the Trail and centrally located to all distilleries in the state

4.99 out of 5 average rating, 85 reviews

Cabin in Lawrenceburg

Hidden View Cabin

Welcome to Hidden View Cabin, a delightful cabin where seeing wildlife and listening to the sounds of nature are yours to enjoy! Take the scenic drive down the gravel lane to this private and peaceful place located among pine trees and overlooking a one acre pond. Whether you have come to relax and get away from it all or want to visit the many attractions throughout central Kentucky this is the place for you. Only 20 minutes from Lawrenceburg.

Superhost

4.74 out of 5 average rating, 113 reviews

2 Bed/2.5 Bath Restored Beauty - Pistachio Palace

Built 1904 and recently lovingly restored. Just 2 blocks off historical Main Street in Shelbyville with great antique and coffee shops, as well as some favorite pubs and restaurants. In the middle of the Bourbon trail and Horse country, short drive to the new Convention Center and the Outlet Mall. This neighborhood is in the midst of gentrification. 2 Queen Beds, one Roll-away, pack-n-play & high chair. Absolutely no pets, including service dogs.

5 out of 5 average rating, 29 reviews

The Back 40 ~ Modern*Bourbon*Scenic*Private

The Back 40...where rural charm meets the modern amenities you expect. Overlooking the Jeptha Creek and situated in a serene Kentucky cattle pasture, this piece of country gold is your gateway to Kentucky's lauded Bourbon Trail and the Saddlebred Capital of the World. The Back 40 is perfect for Bourbon Trail adventurers, those seeking a little retail therapy, or folks simply aiming to escape to a slower pace of life for just a spell.

4.87 out of 5 average rating, 152 reviews

Home in Simpsonville

Charming 4 Bedroom classic home bourbon trail!

Comfortable, newly furnished home located in downtown Simpsonville. This is brand new to AirBnB. Whether you are going down the Bourbon trail or you just want to be near I64 and Louisville, this home is the place for you. Fun, homey well decorated this place offers family fun with Fire pit, backyard and patio. High speed 300mb internet for those workers on the go.

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Other great holiday rentals in Shelby County

4.96 out of 5 average rating, 25 reviews

Farm stay in Shelbyville

The Farm cottage

LuisRating, 5 stars1 month ago

Without a doubt, I feel very comfortable and I was able to take a good rest and relax my mind. I would definitely come back. Thank you very much for your trust.

5 out of 5 average rating, 28 reviews

Bourbon by the Lake

JesseRating, 5 stars1 day ago

The house was perfect, the beds were soft and the host was very responsive. We would absolutely stay again, and our kids enjoyed the kayaking, fishing, and fireflies. The location was close to many distilleries and food options while also allowing a private peaceful experience. We were very pleased with our stay. The dock on the water was a big plus!

5 out of 5 average rating, 15 reviews

Farm stay in Shelbyville

Charming Bourbon Country Retreat on Beautiful Farm

Dina NicholeRating, 5 stars7 months ago

Chickapoo Farm is a hidden Gem in Kentucky! My mother, myself, and my two daughters had a wonderful stay at The Horse and The Hound. The views of the sunrise and sunset were perfect. The home is right next to the flower farm. We loved seeing all the flowers. There are great trails to walk on, delicious grass fed beef for purchase, a stocked pond for fishing, and the option to pick your own flower arrangement. The hosts were unbelievably kind and quick to respond to any questions and concerns. We will definitely be planning another visit.

4.98 out of 5 average rating, 62 reviews

Home in Frankfort

MacAttie Acres

TriciaRating, 5 stars1 week ago

Well, our group of 9 had an enjoyable time in this home! It was as advertised and extremely clean, comfortable and quiet. Cindy was just the sweetest and most respectful host always available to answer questions or give recommendations. Close to great distilleries and downtown Frankfort with cute shops and dining. The pool and hot tub were clean and working and the home was well stocked with basic necessities. Highly recommended and can't wait to come back!

Guest suite in Shelbyville

4.98 out of 5 average rating, 62 reviews

Spacious suite, country views, pool table, firepit

SusanRating, 5 stars2 months ago

Loved staying at Kelly's place!! It was so beautiful, I spent as much time as I could on the covered patio! Beautiful garden and yard that was so peaceful.... Kelly thought of most everything and provided a very good system of how things should be done. She was kind and checked in to ensure my needs were met. Horse, cow & sheep country was enchanting.... I would absolutely stay in Kelly's place again! Susan

5 out of 5 average rating, 37 reviews

Historic Downtown~Heart of Bourbon Trail

RebeccaRating, 5 stars3 weeks ago

Stayed at the Washington Belle for my wedding weekend and it was perfect! Myself and my bridesmaids got ready there and there was plenty of space, light, and rooms to get ready in! Everywhere is decorated so cute and the house is perfectly situated to the Shelbyville Conference Center and the downtown Main Street. We loved staying there and the host is so nice! Such a charming house!

4.93 out of 5 average rating, 14 reviews

Shelbyville, KY - Bourbon Trail and Horse Country.

KerstinRating, 5 stars3 weeks ago

We enjoyed the spacious home with plenty of indoor and outdoor space to relax. The linens, bathrooms, and kitchen were very clean. We appreciated that the home is pet friendly and it was easy to walk our small dogs around the neighborhood. Angus was very responsive to our booking and request. We would stay here again and conveniently located near Shelbyville Country Club.