Holiday houses in Shelbyville
Find and book unique accommodation on Airbnb
Quick stats about holiday rentals in Shelbyville
Total holiday rentals
Explore 50 holiday rentals in Shelbyville
Nightly prices starting at
Shelbyville holiday rentals start at $152 NZD per night before taxes and fees
Verified guest reviews
Over 2,680 verified reviews to help you choose
Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities
Pet-friendly accommodation
Find 20 rentals that welcome pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wi-Fi availability
50 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!
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Bourbon Trail Game Room Hot Tub Speakeasy FirePit
Gather your crew for an unforgettable stay in Kentucky bourbon country. Magnolia Bourbon Manor is a beautifully restored historic home that sleeps 10, featuring a private speakeasy, covered hot tub, fire pit, and pool-table game room. Just 3 minutes from downtown Shelbyville, 12 minutes from Jeptha Creed and Bulleit, and 35 minutes from Louisville, it’s the perfect home base for Bourbon Trail adventures, weekends with friends, family getaways, and celebrations. Proudly hosted by a Superhost and
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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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Hot Tub ~ Art Gallery ~ Bourbon Trail ~ KY Derby
Soak in your private hot tub, step into a one-of-a-kind art gallery, and wake up 30 minutes from the Kentucky Derby. This renovated Victorian cottage blends spa-level comfort with local artistry, the perfect base for Bourbon Trail adventures, horse show weekends, or a group getaway nobody will forget. Three ensuite bedrooms, a gourmet kitchen, and a covered porch await. ✔ Hot Tub · Art Gallery ✔ 3BR/3BA Ensuite · Bourbon Trail ✔ KY Derby 30 min · BBQ Porch ✔ Wi-Fi · Smart TVs · Self Check-In
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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
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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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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 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.
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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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Bourbon & Bluegrass Retreat | Fun & Cozy Stay
Welcome to the Bourbon & Bluegrass Retreat — a fun, thoughtfully designed stay where modern comfort meets Kentucky charm. Each room is full of color, personality, and cozy touches made for relaxing and memory-making. Perfect for couples, friends, or families looking for something unique. Close to local favorites, outdoor adventures, and small-town charm. Come for the stay, leave with memories
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Ideal Location + Futuristic Decor | Galaxy Getaway
Welcome to Galaxy Getaway! This cosmic-themed studio on 6th Street in Shelbyville, KY, offers unique, out-of-this-world amenities for an unforgettable getaway. Whether you’re here to relax or embark on an adventure, your galactic escape starts here! 📍Prime Location 👾 Variety of fun games 🚀 Out of this world decor ✨ Modern amenities
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Popular amenities for Shelbyville holiday rentals
Other great holiday rentals in Shelbyville
Bourbon Country Farm Stay | 6BR | Updated 2026
LocationValueGetting around
The Rec Farm-Log Cabin, Private Lake & Arcade
LocationFamilyIndoor spaces
Hitching Post on the Bourbon Trl
LocationFamilyKitchen
1909 BourbonTrail Gem | 4 King Beds | Fire Pit
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End of Summer Vacation Getaway
LocationFamilyDecor
High Rollers' Retreat w/pool and Pond
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Country Retreat on Bourbon Trail - Fire Pit - King
LocationFamilyAccuracy
Brown Ave Bourbon Trail & Beds- Shelbyville, KY
LocationFamilyBackyard
When is the best time to visit Shelbyville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $338 NZD | $330 NZD | $359 NZD | $447 NZD | $453 NZD | $396 NZD | $353 NZD | $325 NZD | $372 NZD | $426 NZD | $321 NZD | $325 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 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.
Destinations to explore
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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
- University of Kentucky
- Waterfront Park
- Kentucky International Convention Center
- 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