Vacation rentals in Shelbyville
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Quick stats about vacation rentals in Shelbyville
Total vacation rentals
Explore 50 vacation rentals in Shelbyville
Nightly prices starting at
Shelbyville vacation rentals start at G$18,813 GYD per night before taxes and fees
Verified guest reviews
Over 2,680 verified reviews to help you choose
Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 20 rentals that welcome pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wi-Fi availability
50 of Shelbyville vacation 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 vacation rentals in Shelbyville
Guests agree: these stays are highly rated for location, cleanliness, and more.
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.
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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!
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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!)
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Bourbon Trail*4BR*Dog Friendly*6beds (3king)*Patio
A great centrally located 4 BR 2.5 Bath (6 beds) dog-friendly house near downtown Shelbyville! Located in a cul-de-sac on a quiet street in a family friendly neighborhood 6 miles from Bulleit Bourbon, 3 miles to Jeptha Creed Distillery, and 1 mile from the Shelbyville Horse Show. Fully updated & stocked, coffee pot (K-cups or ground), washer/dryer, & 5 smart TVs. This rental has everything you need and proximity to Churchill Downs, multiple Bourbon Trail distilleries, Louisville, and Frankfort!
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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
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Brown Ave Bourbon Trail & Beds- Shelbyville, KY
Welcome to Brown Avenue Bourbon and Beds, a beautifully renovated 1950's charmer on the Bourbon Trail, near the Shelby County Fairgrounds & just minutes from downtown Shelbyville. Start your day w/ coffee on the front porch swing, enjoy an afternoon snack on the back deck, cook dinner in the fully stocked kitchen & cozy up in the living room for movie night after a long day of exploring! A short drive to Louisville, Lexington, Frankfort, KY Derby and PGA Championship 2024 @ Valhalla! Sleeps 6
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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
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End of Summer Vacation Getaway
The Perfect Getaway! Saddlebred Suites offers visitors an upscale loft experience in historic Shelbyville. Our suites are designed to offer guests modern amenities while preserving the historic integrity of the 1890’s building. Exposed brick, renovated bathrooms, and beautiful hardwood flooring invite guests to the quaint, small town charm of downtown Shelbyville. Perfect for large and small groups exploring Kentucky. Perfect for family reunions, bachelorette weekends, and corporate retreats.
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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.
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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.
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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.
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Kentucky Estate: Speakeasy, Theater & Sleeps 20
Oak & Ember Estate is an 8-bedroom Kentucky retreat sleeping up to 20 on 5 private acres. Hidden speakeasy with poker table, private cinema, converted garage game room with putting green and billiards, hot tub, pickleball court, and a gourmet kitchen built for groups. 30 minutes from Churchill Downs. The perfect home base for bourbon trail adventures, Derby weekend, family reunions, and corporate retreats. Guests say they never wanted to leave.
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Popular amenities for Shelbyville vacation rentals
Other great vacation rentals in Shelbyville
The Hutch on Hardesty
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Country Retreat on Bourbon Trail - Fire Pit - King
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1909 BourbonTrail Gem | 4 King Beds | Fire Pit
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Hot Tub ~ Art Gallery ~ Bourbon Trail ~ KY Derby
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Hot Tub | Firepit | Putting Green | 5 Bedrooms
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Bourbon Country Farm Stay | 6BR | Updated 2026
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Bourbon Trail! Game Room Hot Tub Speakeasy FirePit
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Peaceful Bourbon trail home POOL hot tub 3 kings
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When is the best time to visit Shelbyville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$41,807 GYD | G$40,762 GYD | G$44,316 GYD | G$55,185 GYD | G$56,022 GYD | G$48,914 GYD | G$43,689 GYD | G$40,135 GYD | G$45,988 GYD | G$52,677 GYD | G$39,717 GYD | G$40,135 GYD |
| 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 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.
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.
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- Ark Encounter
- Kentucky Exposition Center
- Kentucky Horse Park
- Buffalo Trace Distillery
- Kentucky Kingdom & Hurricane Bay
- Rupp Arena
- Kentucky Derby Museum
- Louisville Slugger Field
- Churchill Downs
- Kentucky International Convention Center
- University of Kentucky
- Waterfront Park
- University of Louisville
- Louisville Slugger Museum & Factory
- Jefferson Memorial Forest
- Falls of the Ohio State Park
- Muhammad Ali Center
- Castle & Key Distillery
- James B Beam Distilling
- Angel's Envy Distillery
- Bernheim Arboretum and Research Forest
- Bardstown Bourbon Company
- Frazier History Museum
- Big Four Bridge