Vacation rentals in Shelbyville
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Top-rated vacation rentals in Shelbyville
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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)
Bourbon, Bridles and 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!
Bourbon Trail*Hot Tub*Sauna*Mini Golf*Wi-Fi*EVSE
Welcome to The BarrelWoods, the perfect retreat in the heart of the Bourbon Trail. This newly built home blends modern luxury with rustic charm, featuring designer touches throughout.Relax by the outdoor firepit, soak in the hot tub, or rejuvenate in the barrel sauna.Enjoy mini golf, archery, disc golf, and a game room with air hockey, shuffleboard, and more.Ideally located near iconic distilleries, fine dining, and scenic parks, The BarrelWoods is the ultimate base for an unforgettable getaway.
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!
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
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.
KY’s #1 Wishlisted Stay-Treehouse and outdoor tubs
Escape to Kentucky’s 2026 most wishlisted Airbnb! A romantic treetop getaway with two outdoor tubs, twinkle lights, and a peaceful setting made for reconnecting. The treehouse features a large glass rolling garage door allowing stunning views of the sunset. The highlight is undoubtedly the double tubs overlooking the creek. ✔ Queen Bed ✔ Outdoor Deck with Seating ✔ Double Outdoor Bathtubs ✔ Outdoor Shower ✔ Composting Toilet ✔ Creek Access ✔ Indoor Cooking Station ✔ Hot Water
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.
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.
My Old Kentucky Dome
An elevated camping “glamping” experience. This brand-new one of a kind geodesic dome is located on a private road that leads you to an overlook featuring one of the most beautiful countryside views in Kentucky. While this getaway experience is nestled deep in the woods, it is also a close drive to all the conveniences you can imagine. This is an off the grid outdoor experience with a ½ mile gravel road including a steep hill. AWD or 4WD advised.
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
Popular amenities for Shelbyville vacation rentals
Other great vacation rentals in Shelbyville
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Bourbon Trail~Hot Tub~Sleeps 10~Firepit~Gameroom
KY Cottage near Bourbon, Expo & Horse Park|Hot Tub
Sip, Soak & Stay | Bourbon Trail Lakehouse Gem
Central KY - Downtown Boutique Suites
Hot Tub | Firepit | Putting Green | 5 Bedrooms
Parris on Main St - Downtown, Bourbon and Derby!
When is the best time to visit Shelbyville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$41,833 GYD | G$40,788 GYD | G$44,343 GYD | G$37,859 GYD | G$39,742 GYD | G$37,859 GYD | G$43,716 GYD | G$40,160 GYD | G$46,017 GYD | G$52,710 GYD | G$39,742 GYD | G$40,160 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.
Quick stats about vacation rentals in Shelbyville
Total vacation rentals
Explore 40 vacation rentals in Shelbyville
Nightly prices starting at
Shelbyville vacation rentals start at G$20,917 GYD per night before taxes and fees
Verified guest reviews
Over 2,470 verified reviews to help you choose
Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 10 rentals that welcome pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wi-Fi availability
40 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!
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