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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 ﺩ.ﺇ 331 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.

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Top guest favorite
Home in Shelbyville

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!

5.0 out of 5 average rating, 25 reviews
Guest favorite
The exterior of a single-story brick house is shown under a clear blue sky. A driveway leads to a two-car garage, and a landscaped front yard features green grass and shrubs. A large window above the entrance highlights the architectural design.
Home in Shelbyville

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!

4.97 out of 5 average rating, 68 reviews
Guest favorite
Home in Shelbyville

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

4.97 out of 5 average rating, 29 reviews
Guest favorite
Loft in Shelbyville

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

4.98 out of 5 average rating, 113 reviews
Top guest favorite
Farm stay in Shelbyville

Beautiful Farm Stay on the bourbon trail!

This memorable place is anything but ordinary. Enjoy the picturesque views from the farmhouse of the pastures. Watch as the sheep and horses graze. On the hour you can hear the sound of church bells. When the wind is right, the smell of mash from local distilleries wafts through the air. Make one of a kind memories on our beautiful farm. Included in your stay are fresh farm eggs (when available), enough coffee, creamer, sugar for the first morning, and 6 bottles of water and farm tour.

4.99 out of 5 average rating, 67 reviews
Guest favorite
A bright living area features two white sofas, accented with colorful throw pillows. A rustic wooden coffee table sits centrally, displaying drinks. Two plaid armchairs are positioned across from the sofa, and vibrant artwork of cows adorns the wall, enhancing the inviting decor.
Home in Shelbyville

Hitching Post on the Bourbon Trl

The Hitching Post on the Bourbon Trail – Spacious Shelbyville retreat near charming downtown & walkable to the famous Horse Show. Minutes from Louisville & centrally located to top distilleries. Enjoy a man cave with poker, darts, shuffleboard & big screen TV, plus a screened porch for coffee or bourbon. Kids will love the playhouse over a stream in a fenced yard. Located in a safe, scenic community in the Saddlebred Capital of the World—your perfect base for bourbon & horse country!

5.0 out of 5 average rating, 13 reviews
Top guest favorite
Home in Shelbyville

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.

5.0 out of 5 average rating, 33 reviews
Top guest favorite
A comfortable living area features a neutral-colored sofa and a wooden coffee table. A ceiling fan hangs above, while a television is mounted on the wall above a decorative fireplace. Natural light enters through two windows, complemented by rustic wall accents.
Guesthouse in Shelbyville

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.

4.97 out of 5 average rating, 148 reviews
Guest favorite
The spacious living area features large windows allowing ample natural light. Elegant details include high ceilings and exposed brick walls. A plush sofa is arranged around a coffee table, while a dining area with a wooden table is visible in the background.
Loft in Shelbyville

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.

4.91 out of 5 average rating, 55 reviews
Guest favorite
Home in Shelbyville

Hot Tub | Firepit | Putting Green | 5 Bedrooms

Picture this: the fire pit crackles while bourbon stories spill into the Kentucky night, steam rises off the hot tub under string lights, and someone's lining up a putt on your own backyard green. Ten of your favorite people, one quiet Shelbyville street, minutes from the world's most famous bourbon trail. This isn't just somewhere to sleep between distillery tours — it's the trip everyone keeps talking about after.

4.88 out of 5 average rating, 26 reviews
Guest favorite
Home in Shelbyville

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.

5.0 out of 5 average rating, 9 reviews
Guest favorite
Home in Shelbyville

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

4.87 out of 5 average rating, 31 reviews

Popular amenities for Shelbyville vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Shelbyville

Guest favorite
Home in Shelbyville

Lakefront - Bourbon Trl - Hot Tub

5.0 out of 5 average rating, 79 reviews
Top guest favorite
An outdoor fire pit area is featured, surrounded by several adirondack chairs arranged on a gravel surface. String lights illuminate the space, creating a warm ambiance. In the background, the house is partially visible, with an inviting seating area under a canopy.
Home in Shelbyville

Bourbon Trail! Game Room Hot Tub Speakeasy FirePit

4.97 out of 5 average rating, 65 reviews
Guest favorite
A living room features a deep blue accent wall and a circular coffee table atop a patterned rug. An orange couch is paired with two brown leather armchairs, while a stylish light fixture hangs overhead. A framed artwork is displayed above a traditional fireplace.
Home in Shelbyville

Historic Centrally Located Gem •Hot Tub •Sleeps 10

4.92 out of 5 average rating, 36 reviews
Top guest favorite
Cabin in Shelbyville

The Rec Farm-Log Cabin, Private Lake & Arcade

5.0 out of 5 average rating, 23 reviews
Top guest favorite
A two-story guest house is situated amid lush green grass and shade trees. The exterior features a combination of light siding and dark accents, with a covered porch furnished with chairs. Windows allow natural light to engage the interior, enhancing the peaceful rural setting.
Farm stay in Shelbyville

Annola Farm Guest House

4.98 out of 5 average rating, 62 reviews
Top guest favorite
A charming single-level home is presented with a welcoming front porch featuring rocking chairs. Lush grass and neat landscaping frame the stone pathway leading to the front door. Trees provide shade, creating a serene setting in a quiet neighborhood.
Home in Shelbyville

Brown Ave Bourbon Trail & Beds- Shelbyville, KY

5.0 out of 5 average rating, 66 reviews
Top guest favorite
An inviting historic home with a vibrant blue exterior is showcased against a clear sky. The front door, adorned with multiple panes of glass, complements the white trim and large windows. Lush greenery surrounds the entrance, enhancing the charm of this property.
Home in Shelbyville

Historic Downtown~Heart of Bourbon Trail

5.0 out of 5 average rating, 66 reviews
Top guest favorite
Home in Shelbyville

Bourbon Country Farm Stay | 6BR | Updated 2026

4.93 out of 5 average rating, 90 reviews

When is the best time to visit Shelbyville?

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Avg. priceﺩ.ﺇ 735ﺩ.ﺇ 716ﺩ.ﺇ 779ﺩ.ﺇ 970ﺩ.ﺇ 984ﺩ.ﺇ 859ﺩ.ﺇ 768ﺩ.ﺇ 705ﺩ.ﺇ 808ﺩ.ﺇ 925ﺩ.ﺇ 698ﺩ.ﺇ 705
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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