Ferieboliger i Shelbyville

Romantic Cozy Cabin Getaway w/ Firepit & Hot Tub

Privately nestled on over 5 wooded acres & intentionally curated for your stay. Gain access to quiet, immerse yourself in nature, support your rejuvenation, & to tap into your creative flow. Amenities include on-site hiking trail, artist work space, wood burning stove, covered porch, hammocks, outdoor dining, fire pit, moon garden, salt-water hot tub, & outdoor shower. Close to Beaver Lake & located along the Bourbon Trail, just minutes from Wild Turkey & Four Roses distilleries. (Note:18+only)

Bourbon, Bridles & Birdies Retreat

We would LOVE to welcome you to Bourbon, Bridles & Birdies Retreat! Nestled in a quiet & peaceful neighborhood in the historic district of downtown Shelbyville, this FAMILY-FRIENDLY home offers unique dining experiences, seriously good shopping & the fairgrounds less than a mile walk away. Do you have plans in the big city?This thoughtfully laid out, detail-packed home will be your perfect retreat to relax. Please see "The Space" section for all the amazing attractions Shelbyville has to offer!

Parris on Main St - Downtown, Bourbon and Derby!

Close to everything when you stay at this centrally-located place. Parris on Main Street is the perfect location to enjoy the historic town of Shelbyville, a few blocks walking distance to many antique shops, local coffee houses and great locations to grab a bite. 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

Close to all the popular distilleries Perfect Spot

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. Come see what this space has to offer

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.

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.

Jeptha Crest-Bourbon Trail, Hot Tub, Sauna, Dog OK

Jeptha Crest is a designer-built and thoughtfully decorated home, perfectly placed in the heart of the Bourbon Trail yet hidden among trees and nature views. Though centrally located, it feels like a private forest escape, offering rare privacy and calm. A spacious two-level deck, fire pit, hot tub, and sauna invite you outdoors, while inside, clean modern design blends seamlessly with warm, cozy comfort — a refined retreat created for slowing down and truly unwinding.

Cozy Kentucky Winter, Bourbon Trail, Location!

♡ Meet The Blue Belle: a beautifully restored 1880s cottage ON the Bourbon Trail, nestled on a peaceful block in the heart of Shelbyville. Start your day with a coffee on the back deck, make s'mores by the fire pit, cook dinner in the fully stocked kitchen, & cozy up in the living room for movie night after a long day of exploring & bourbon! A short drive to Louisville, Lexington, & Frankfort and other great areas. Comfortably sleeps 8. Perfect for families & couples!

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.

Bourbon Country Cabin

Nestled in the Heart of Bourbon Country sitting on 80 acres of Kentucky woodlands this charming loft style cabin makes a great central location to visit all the local distilleries on the Kentucky Bourbon Trail! Enjoy exploring the walking trails, creek, and the property while you stay in a peaceful cabin in the woods! Check out our other listing too if you have a large group and would like to book both rentals. Bourbon Country Cottage

Sip on bourbon in the hot tub! +hiking & game shed

A charmingly unique taste of KY waits for you at this peaceful log cabin! 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! Your next adventure is just a peaceful countryside drive away at the Kentucky Bourbon Den!

1909 BourbonTrail Gem | 4 King Beds | Fire Pit

Discover The Copper & Oak, a beautifully restored 1909 home in downtown Shelbyville. This spacious 4-bedroom, 4-bath property features two full living spaces connected by a speakeasy-style door, fully stocked kitchens, king bedrooms, and cozy gathering areas. Enjoy shuffleboard, the covered patio, and walkable access to shops, dining, and the Kentucky Bourbon Trail. Perfect for groups seeking comfort and charm.