Holiday houses in Shelbyville
Find and book unique accommodation on Airbnb
Quick stats about holiday rentals in Shelbyville
Total holiday rentals
Explore 40 holiday rentals in Shelbyville
Nightly prices starting at
Shelbyville holiday rentals start at $176 NZD per night before taxes and fees
Verified guest reviews
Over 2,470 verified reviews to help you choose
Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities
Pet-friendly accommodation
Find 10 rentals that welcome pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wi-Fi availability
40 of Shelbyville holiday rentals include Wi-Fi access
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Shelbyville rentals
4.9 Average rating
Shelbyville stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated holiday rentals in Shelbyville
Guests agree: these stays are highly rated for location, cleanliness and more.
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!
Close to Buffalo Trace/Transpo available-Must See
Best place to stay on the Bourbon Trail FEATURED on HGTV! Swanky! Stunning! Spectacular! You'll be in a top-floor loft overlooking downtown Shelbyville and perfectly situated in the heart of the Bourbon Trail! Incredible place to stay for Derby, Keeneland, PGA or local weddings and events---if you can pry yourself away from here! We specialize in making your stay an over-the-top experience and are happy to arrange chauffeured transportation, private chef accommodations, and dinner reservations.
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.
Historic Downtown~Heart of Bourbon Trail
The Washington Belle is an historic home, freshly renovated with all the modern conveniences, centrally located in Shelbyville, Kentucky. She's the perfect base from which to explore the distilleries of the Bourbon Trail, with easy access to Louisville and Lexington. There are multiple restaurants, cafes, bourbon bars and antique stores in easy walking distance. Boasting two large living areas, three large bedrooms (including a master with ensuite), 2.5 baths, and private off street parking
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.
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.
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!
Popular amenities for Shelbyville holiday rentals
Other great holiday rentals in Shelbyville
2 Bed/2.5 Bath Restored Beauty - Pistachio Palace
Annola Farm Guest House
Hot Tub ~ Art Gallery ~ Bourbon Trail ~ KY Derby
The Rec Farm-Log Cabin, Private Lake & Arcade
Ideal Location + Futuristic Decor | Galaxy Getaway
Bourbon Trail*4BR*Dog Friendly*6beds (3king)*Patio
Parris on Main St - Downtown, Bourbon and Derby!
Private A-frame Cabin | Hot tub, Firepit & Views
When is the best time to visit Shelbyville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $352 NZD | $344 NZD | $374 NZD | $319 NZD | $335 NZD | $319 NZD | $368 NZD | $338 NZD | $388 NZD | $444 NZD | $335 NZD | $338 NZD |
| Avg. temp | 1°C | 3°C | 7°C | 13°C | 18°C | 22°C | 24°C | 23°C | 20°C | 14°C | 7°C | 3°C |
Frequently Asked Questions
What are the best things to do in Shelbyville with kids?
Kids often enjoy playgrounds in community parks, visits to interactive museums, or meeting animals at a local farm. Seasonally, family-friendly festivals and creative workshops are organized for younger guests.
What are some of the best things to do in Shelbyville?
Explore artisan shops and eateries in historic downtown, or experience the region’s equestrian heritage at a horse farm or event. Nature lovers can enjoy scenic parks, especially during the changing seasons.
How is the weather in Shelbyville?
Shelbyville’s winters are brisk, with temperatures around 25–45°F (-4–7°C), while summers feel warm, reaching 82–84°F (28–29°C). Spring and fall bring mild weather and more rainfall, so layering is suggested year-round.
When is the best time to visit Shelbyville?
Late spring and early fall are often recommended for pleasant temperatures and lively local events. Summer draws visitors for outdoor activities, while winter brings quieter streets and festive decorations.
What are the best places to visit in Shelbyville?
Visit Shelbyville’s historic downtown for local shops and public art, or explore nearby equestrian centers that highlight the area’s horse culture. Parks and small museums introduce the region’s stories and traditions.
What are some hiking trails in Shelbyville?
Shelbyville has accessible nature trails in area parks and surrounding green spaces. Many visitors enjoy forested paths, open meadows, and creek-side walks ideal for a relaxed outing.
What are some family activities we can do in Shelbyville?
Families often enjoy community parks, hands-on museums, and exploring local nature trails together. Seasonal festivals, farmers markets, and small event centers add extra options for group fun.
What are some of the best day trip ideas from Shelbyville?
Explore nearby bourbon distilleries, visit outdoor recreation areas, or discover neighboring towns with antique shops and historic landmarks. Art galleries, local farms, and equestrian tours are also frequently suggested.
Are there any pet friendly accommodations available in Shelbyville?
Shelbyville has pet-friendly accommodations, especially in homes and rentals near parks or open countryside. Many places welcome pets, and nearby walking paths and green spaces make outings convenient.
What are some local tips for visiting Shelbyville?
Take time to explore Shelbyville's historic downtown, which has independent shops and local eateries. Many travelers appreciate the welcoming atmosphere, and stopping by a farmers market or craft fair can add a local touch to your visit.
What is Shelbyville known for?
Shelbyville is often recognized for its roots in American Saddlebred horse breeding, historic downtown, and welcoming local businesses. The area also has ties to bourbon heritage and regional crafts.
What are the best hidden gems to explore in Shelbyville?
Shelbyville has tucked-away art studios, quiet walking paths, and family-owned bakeries that reward curious travelers. Joining a workshop with a local craftsperson or stopping by a lesser-known gallery can add depth to your visit.
What are the best foods to try in Shelbyville?
Shelbyville is known for Southern-influenced dishes, including fried chicken, locally sourced barbecue, and country-style sides. Be sure to sample seasonal produce and baked goods from local markets and cafés.
What should I bring for a trip to Shelbyville?
Bring comfortable walking shoes for historic neighborhoods, and pack layers to accommodate changing Kentucky weather. A light rain jacket is useful in spring and fall, while sun protection is suggested during warmer months.
What is the nightlife in Shelbyville like?
Shelbyville has a relaxed nightlife scene, with cozy pubs, family-owned restaurants, and casual spots for live music. Some visitors join locals at breweries or attend small music performances around the downtown area.
What are the most popular events or festivals in Shelbyville?
Shelbyville hosts seasonal festivals celebrating local heritage, crafts, and the region's equestrian culture. Events tied to spring and fall, as well as festivities around Labor Day weekend, are frequently suggested for a vibrant community experience.
Are there family friendly vacation rentals in Shelbyville?
Many family-friendly rentals are available in and around Shelbyville, with options that have spacious yards and access to neighborhood parks. Look for homes near downtown or in nearby rural settings for a comfortable family stay.
What are the best places to stay in Shelbyville?
Look for accommodations near historic downtown for easy access to local dining and shops, or explore rural stays around the countryside for a quieter setting. Both options allow guests to experience the region’s distinct atmosphere.
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- Ark Encounter
- Kentucky Exposition Center
- Kentucky Horse Park
- Buffalo Trace Distillery
- Rupp Arena
- Kentucky Kingdom & Hurricane Bay
- Churchill Downs
- Kentucky Derby Museum
- Louisville Slugger Field
- University of Kentucky
- Waterfront Park
- University of Louisville
- Falls of the Ohio State Park
- Louisville Slugger Museum & Factory
- Kentucky International Convention Center
- Jefferson Memorial Forest
- Muhammad Ali Center
- Angel's Envy Distillery
- Big Four Bridge
- Castle & Key Distillery
- Bernheim Arboretum and Research Forest
- James B Beam Distilling
- Frazier History Museum
- Kentucky Science Center