Holiday houses in Shelbyville
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Shelbyville
Guests agree: these stays are highly rated for location, cleanliness and more.
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)
LocationValueQuiet
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!
FamilyLocationCleanliness
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
FamilyLocationWalkability
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
FamilyValueCheckout
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.
LocationFamilyOutdoor spaces
Bourbon Trail: Caboose on the Farm
Nestled under the shadows of 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 bunkbeds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!
FamilyValueBiking
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.
FamilyValueNearby
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!
FamilyLocationHospitality
Annola Farm Guest House
Stay and be delighted with this newly renovated two-story guest house which adjoins our 11-stall horse barn. Framed by covered porches and shade trees, our guest house is a wonderful place to unwind and relax during your stay in beautiful central Kentucky. The best of both worlds--a lovely rural setting situated only minutes from the interstate, making travel to Churchill Downs, Valhalla Golf Course, and other attractions in nearby Louisville and Frankfort a breeze.
ValueFamilyWi-Fi
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.
FamilyValueBathroom
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.
LocationFamilyComfort
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!
FamilyLocationHiking
Popular amenities for Shelbyville holiday rentals
Other great holiday rentals in Shelbyville
Ideal Location + Futuristic Decor | Galaxy Getaway
ValueLocationHospitality
Bourbon Trail*4BR*Dog Friendly*6beds (3king)*Patio
FamilyValueBackyard
Hot Tub | Firepit | Putting Green | 5 Bedrooms
LocationFamilyAmenities
Parris on Main St - Downtown, Bourbon and Derby!
FamilyLocationGetting around
Bourbon Trail Getaway~Hot Tub, Pets OK, Game Room
FamilyLocationAmenities
Bourbon Trail Country Getaway
LocationFamilyAccuracy
Private A-frame Cabin | Hot tub, Firepit & Views
ValueLocationNearby
Bourbon & Bluegrass Retreat | Fun & Cozy Stay
LocationFamilyDecor
When is the best time to visit Shelbyville?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $285 AUD | $278 AUD | $302 AUD | $258 AUD | $271 AUD | $258 AUD | $298 AUD | $274 AUD | $314 AUD | $360 AUD | $271 AUD | $274 AUD |
| 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.
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 $143 AUD 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!
Destinations to explore
- Nashville Holiday rentals
- Chicago Holiday rentals
- Sevierville Holiday rentals
- Gatlinburg Holiday rentals
- Pigeon Forge Holiday rentals
- Indianapolis Holiday rentals
- Columbus Holiday rentals
- Asheville Holiday rentals
- St. Louis Holiday rentals
- Cleveland Holiday rentals
- Louisville Holiday rentals
- Cincinnati Holiday rentals
- Ark Encounter
- Kentucky Exposition Center
- Kentucky Horse Park
- Buffalo Trace Distillery
- Rupp Arena
- Churchill Downs
- Kentucky Kingdom & Hurricane Bay
- Kentucky Derby Museum
- Louisville Slugger Field
- University of Kentucky
- Kentucky International Convention Center
- Louisville Slugger Museum & Factory
- Falls of the Ohio State Park
- University of Louisville
- Waterfront Park
- Muhammad Ali Center
- Jefferson Memorial Forest
- Angel's Envy Distillery
- Big Four Bridge
- Against The Grain Brewery & Smokehouse
- Bernheim Arboretum and Research Forest
- James B Beam Distilling
- Castle & Key Distillery
- Kentucky Science Center