Vacation Rentals By Owner In Shelbyville, KY

$424.84

KY Bourbon Trail Home, King Bed, FirePit, Near Louisville

Shelbyville, Kentucky, United States

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 smores 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. Comfortably sleeps 4 adults & 1 child. Perfect for small families & couplesbrbrThe home is a single level, 2 bedroom, 2.5 bathroom historical cottage which is a perfect spot for small families, couples, and friends! Whether you're planning a full day of Kentucky exploring and bourbon tasting or unwinding in the home, the quiet, historical street provides the perfect escape for your getaway. The home is minutes away from distilleries, grocery stores, restaurants, parks, and the shops of downtown Shelbyville. There is plentiful other distilleries and activities within a 30 minute drive of The Blue Belle.brbrThe open living room features extra comfortable seating and a Smart TV. Guests will immediately notice the gorgeous window that is the focal point of the living room. There are only 4 of these breathtaking windows in the area and the rare glass pattern was sourced circa 1890-1905 from Chances Bros. in Birmingham, England.brbrThe dining area seats up to 6 people and is located in the fully equipped kitchen that features custom countertops and a 200 year old antique light fixture. The kitchen has brand new stainless steel appliances, a keurig/drip coffee maker with all your coffee needs, a bean grinder, silverware, plates, cups, bowls, knife set, can opener, measuring cups, mixing bowls, strainer, blender, baking sheets, and ice maker.brbrThere are two charming bedrooms which feature en suite bathrooms. The first is a king bedroom with a smart tv and cozy seating area. The second is a queen bedroom with a seating area and a bathtub. Laundry is located in the half bathroom next to the kitchen.brbrThe Blue Belle is the perfect spot as a base for your Kentucky getaway and is central to all the amazing attractions in the area!br8 mins to Bulliet Whiskeybr10 mins to Talon Winerybr11 mins to Jeptha Creed Distillerybr30 mins to Buffalo Tracebr30 mins to Louisvillebr30 mins to Lawrenceburgbr30 mins to Lover's Leap Winerybr30 mins to Castle & Key Distillerybr30 mins to Rising Sons Home Farm Winerybr27 mins to Kentucky River Toursbr35 mins to Four Rosesbr35 mins to Churchill Downsbr35 mins to Angels Envy Distillerybr35 mins to Louisville Airportbr50 mins to Jim Beambr50 mins to BardstownbrThe home is professionally cleaned and sanitized between every guest stay to the highest standards.brGuest accessbrA unique code will be provided the day before check in.brOther things to notebrGuests will enter The Blue Belle through the back door. Please note the front door has a historical self-locking mechanism.

2

Bed

2

Bath

5

Sleeps

$304.92

/ Nightly

Private Vacation Home

Spacious 4-bedroom house Shelbyville 1 mile from I-64

Shelbyville, Kentucky, United States

Your Shelbyville adventure begins at this 4-bedroom house. Each bedroom features a comfortable queen bed, perfect for a restful night. The house includes two bathrooms, both equipped with a shower and one has a seperate bathtub, making it easy for guests to refresh and unwind. Enjoy a peaceful atmosphere throughout the home, where you can relax after a day of exploring. Whether you’re gathering with friends or family, this amazing space offers everything needed for an enjoyable stay. We look forward to hosting you at our place.

Bed

Bath

Sleeps

$834.75

/ Nightly

Country House

Historic Home Farm Stay in the Heart of Bourbon Country

Shelbyville, Kentucky, United States

Welcome to The Harbison House! This newly renovated historic home is the best of both worlds- all the modern amenities you want with all the charm of a unique step back in time! There are neat treasures to look at in every room. Located in the heart of bourbon country on a family farm, you can take a picnic by the pond while being only a short distance from great restaurants and all the distilleries!brbrThis one of a kind home is featured on the National Registry of Historic Places and dates back to the 1870's. It underwent an extensive renovation is 2023. We have added many modern amenities- including a state of the art chef's kitchen with commercial appliances, while maintaining the original historic finishes of the home.brbrEvery room is unique- with unexpected treasures around every turn. With soaring 11 foot ceilings and floor to ceiling windows, the home is sun soaked and airy. Sit a while in a rocking chair on one of our many porches or cast a line in our stocked pond. Enjoy the serene sounds of nature while only being a short drive to dozens of distilleries.brbrEach bedroom has an ensuite bathroom. Two of our bathrooms boast claw foot tubs. Have a soak while you read a book and recharge. All bedrooms are equipped with a smart tv so you can connect to all your favorite streaming services. We are stocked with board games, playing cards and lawn games.brbrEnjoy a late night poker game or sip of wine in our bourbon parlor. The ambiance in this home is perfect for multiple couples traveling the bourbon trail or just wanting to step off the beaten path to have a truly Kentucky experience.brbrWe've thought of everything in our chef's kitchen. From double ovens to a gas stovetop to an additional wine fridge, we've got everything you need. We provide coffee, tea and flavored syrups so that your morning coffee can be enjoyed on the porch as you watch the geese swim on the pond. We have spices and every imaginable piece of cookware you could need to make the perfect meal. Our dining table was custom made from wood milled off the farm and seats up to 14 people.brbrWe are lifelong residents of Shelby County. We are more than happy to help you plan your trip! If we can help arrange transportation, a restaurant reservation or recommendation please let us know.br

Bed

Bath

Sleeps

$289.38

/ Nightly

Private Vacation Home

Shelbyville, KY - Bourbon Trail, Horse Country and more. A modern, spacious gem.

Shelbyville, Kentucky, United States

Shelbyville is waiting for you at this wonderful 4-bedroom house. With 4 queen beds, this tremendous property offers ample space for guests to relax and unwind. The house features modern amenities such as a washing machine, AC, WiFi, and heating. The 3 bathrooms are equipped with showers and 1 bathtub, ensuring a fantastic stay for everyone. Fall in love with Shelbyville and enjoy the magic it has to offer. There is an adorable cat that thinks she owns this place and comes and goes as she pleases. If that's a problem - we can take her during your stay.

Bed

Bath

Sleeps

$821.34

/ Nightly

Cabin

The Rec Farm - Log Cabin, Private Lake, Hot Tub, Arcade,Pickle Barn, Sleeps 12+

Shelbyville, Kentucky, United States

Previously one of Shelbyville’s top Guest Favorite with 4.9 rating — now refreshed under new ownership, same great experience!brbrThe Rec Farm—a private 13+ acre pet friendly retreat with a renovated log cabin, serene lake views, hot tub, fire pit and game-packed Rec Barn featuring ping pong, ski ball, and more. This hidden retreat combines rustic charm and modern comfort just minutes from I-64. Perfect for families, friends, and bourbon explorers looking to relax, reconnect, and unwind.brbrPets welcome! Bring your furry friends along to enjoy the lake and open fields.brbrThe CabinbrCompletely remodeled in 2022, the warm and welcoming 3-bedroom, 2.5-bath log cabin comfortably sleeps up to 12 guests and features:brbr- MBR - 1 King, 1 Queen (optional)br- BR 1 - 1 Bunk Bed - Full, 1 Twin XLbr- BR 2 - 1 Queen , 1 Twin XLbr- Additional twin mattresses: Can sleep 3 additional guestsbr- Living room couch - Can sleep 2 additional guestsbr- Spacious Great Room with cathedral ceiling and stone wood-burning fireplacebr- Kitchen with premium appliancesbr- First-Floor Master Suitebr- Laundry Room for added conveniencebr- Oversized Deck with stunning lake viewsbr- 8-person hot tub for ultimate relaxationbrbrThe Rec BarnbrThe fun doesn’t stop indoors—head to the adjacent Rec Barn, where everyone can disconnect from screens and reconnect over some classic games:brbr- Arcade Machine with 3,500+ gamesbr- Ski Ball, Ping Pong, Corn Hole, Arcade Basketball & Foosball Tablesbr- ***NEW***Professional grade 10 seater Poker tablebr- Large TV and stereo system perfect for a game night or partying!brbrNEW ADDITION PICKLE BARN**Indoor recreational Pickle Ball court on artificial turf***brbrThe PropertybrSurround yourself with peace, play, and privacy:br- 1-Acre Lake for serene views and outdoor funbr- Fire Pit for s’mores and stories under the starsbr- RV Parking & Hookups availablebrbrWhether you're planning a family escape, friends’ getaway, or a company retreat, The Rec Farm is your all-fun-inclusive destination—where connection, comfort, and good times come naturally.

Bed

Bath

Sleeps

$406.2

/ Nightly

Private Vacation Home

Historic 1909 Gem on the Bourbon Trail w/4 King Beds

Shelbyville, Kentucky, United States

Step inside The Copper & Oak and discover a perfectly restored 1909 home designed for gathering, relaxing, and exploring the best of Kentucky’s Bourbon Trail. Right in the heart of historic downtown Shelbyville — the ideal midpoint between Louisville, Frankfort, and Bardstown — this upscale 4-bedroom, 4-bath getaway blends classic charm with modern comfort.brbrThe home is split into two beautifully appointed units, each offering its own living room, fully stocked kitchen, smart TV, and cozy dining/workspace. A hidden speakeasy-style Murphy door connects the spaces, giving groups the flexibility to spread out while still enjoying time together.brbrThroughout the home, you’ll find warm décor, plush furnishings, and local artwork, including pieces by the 148th Kentucky Derby artist. Every king bedroom is designed for rest and retreat, and all four bathrooms feature stylish tiled showers — with two ensuite for added privacy.brbrStart your day with coffee from either Keurig setup, cook meals in the well-equipped kitchens, or gather for games of shuffleboard, cards, and board games after touring distilleries or horse farms. In the evenings, fire up the grill on the covered patio and enjoy a laid-back Kentucky night.brbrWith private off-street parking and a walkable location near coffee shops, restaurants, and boutiques, The Copper & Oak is a welcoming, comfortable base for your Bluegrass adventure. Make yourself at home and enjoy an unforgettable stay along the Bourbon Trail.brbrbr*** Places to Go ***brbr** 10–15 Minutes **br- Bulleit Distilling Co. – Shelbyvillebr- Jeptha Creed Distillery – Shelbyvillebrbrbr** 30–40 Minutes **br- Lawrenceburg / Versailles / Frankfort / Louisvillebr- Four Roses Distillery – Lawrenceburgbr- Wild Turkey Distillery – Lawrenceburgbr- Woodford Reserve – Versaillesbr- Buffalo Trace – Frankfortbr- Castle & Key Distillery – Millville/Frankfortbr- Whiskey Thief Distilling Co. – Frankfortbr- Louisville Urban Bourbon Experiencebrbrbr** 35–40 minutes **br- Angel’s Envybr- Old Forester Distilling Co.br- Evan Williams Experiencebr- Rabbit Hole Distillerybr- Michter’s Fort Nelsonbrbrbr** 50–60 Minutes **br- Bardstown / Clermontbr- Jim Beam American Outpost – Clermontbr- Bardstown Bourbon Company – Bardstownbr- Heaven Hill Bourbon Experience – Bardstown

Bed

Bath

Sleeps

$243.47

/ Nightly

Condo

Charming 3-bedroom Loft on the Bourbon Trail.

Shelbyville, Kentucky, United States

Relax at our modern-rustic guest house on a peaceful farm in Shelby County, KY—right on the Bourbon Trail. Just 40 mins from Louisville and 50 from Lexington. Features 3 bedrooms (including a loft), a full kitchen, fireplace, Wi-Fi, and a pond for swimming or fishing. Meet our friendly horses, donkeys, and two sweet dogs who love greeting guests at the gate. Perfect for couples, small families, or solo travelers looking to unwind.

Bed

Bath

Sleeps

$233.73

/ Nightly

Lodge

Spacious charming exclusive rental in Shelbyville, KY

Shelbyville, Kentucky, United States

Enjoy a peaceful stay at this marvelous 5-bedroom lodge in Shelbyville. With 4 full beds, 4 twin beds, and 1 queen bed, this cozy retreat is perfect for families or groups of friends. The lodge features 3 bathrooms equipped with towels and soap for your convenience. Experience our close proximity to Bourbon Distilleries and golf courses.

Bed

Bath

Sleeps

$829.21

/ Nightly

Apartment

Centrally Located in Downtown Shelbyville/Boutique Stay/Sleeps 14

Shelbyville, Kentucky, United States

brSaddlebred Suites is your upscale getaway in the heart of historic downtown Shelbyville. Experience the perfect blend of luxury and convenience, essential for wedding parties, weekend getaways, romantic escapes, or curious Kentucky travelers. Our property features four elegant suites comprising a total of 6 bedrooms and 6 bathrooms, accommodating groups of all sizes. Enjoy two inviting common areas that provide breathtaking views of downtown, perfect for relaxation and celebration. Plus, you’ll have exclusive access to the entire upstairs, ensuring your stay is both private and comfortable. If you’re traveling with a smaller group, inquire about reserving half of the property for just 6-8 guests at a reduced rate. Embrace the vibrant downtown lifestyle and create unforgettable memories at Saddlebred Suites!brbrDesigned to offer guests modern amenities while preserving the historic integrity of the 1890 building, Saddlebred Suites features exposed brick, newly renovated bathrooms, beautiful hardwood flooring and the feeling of a big city loft within the quaint, small-town charm of downtown Shelbyville. Guests can walk to a locally-owned coffee shop, one-of-a-kind restaurants, antique stores, boutiques and a community theatre. Centrally located between Louisville and Lexington (and a midway point between Churchill Downs and Keeneland), Saddlebred Suites is a great headquarters for touring bourbon distilleries and horse farms and sampling the heart of the Bluegrass in comfort, elegance and a true sense of small town community. brbrWe ask that you treat our home with the same respect that you do your own.brbrThis is a non-smoking home.brbrIf you do smoke we ask that you do so outside away from the house and that you properly put out and dispose of the cigarette outside.brbrNo open flames or candles are allowed on the property.brbrNo pets are allowed in the house.brbrNo large-scale events or parties are permitted.brbrOnly guests who are on the original booking are allowed stay overnight

Bed

Bath

Sleeps

$357.72

/ Nightly

Private Vacation Home

Historic Gem on the Bourbon Trail at The Copper

Shelbyville, Kentucky, United States

Copper is the private 2-bedroom listing of The Copper & Oak, a beautifully restored 1909 home located in historic downtown Shelbyville, Kentucky. Guests enjoy exclusive use of this entire private retreat — no shared spaces, no other guests on site during your stay. Perfect for couples, small groups, or a relaxing Bourbon Trail getaway, this stylish 2-bedroom, 2-bath retreat blends modern comfort with timeless Southern charm in an ideal location between Louisville, Frankfort, and Bardstown.brbrInside, the home features warm décor, plush furnishings, and thoughtfully curated local artwork, including pieces by the 148th Kentucky Derby artist. The cozy living room creates the perfect place to unwind after a day exploring bourbon distilleries, horse farms, or the charm of downtown Shelbyville, while the smart TV, games, and comfortable seating make it easy to settle in for a relaxing evening.brbrThe fully equipped kitchen offers sleek appliances, open shelving, and everything needed for meals at home, whether you’re starting the morning with coffee from the Keurig or gathering around the dining table after a day along the Bourbon Trail. Both king bedrooms are designed with comfort in mind, featuring premium linens and inviting spaces to recharge at the end of the day. The two stylish bathrooms include modern finishes and beautifully tiled showers for a polished, spa-like touch.brbrOutside, spend your evenings soaking in the hot tub beneath the stars, sharing drinks around the fire pit, or simply enjoying the laid-back atmosphere of Kentucky evenings. With private off-street parking and a walkable location near local coffee shops, restaurants, and boutiques, Copper at The Copper & Oak offers a comfortable and memorable stay in the heart of Bourbon Country.brbrbr*** Please Note ***brThis listing offers exclusive access to the lower unit along with full use of the outdoor amenities, including the covered patio, private hot tub, and fire pit. Although The Copper & Oak is a 4-bedroom property in its entirety, no other guests will be on-site during your stay, allowing you to fully relax and enjoy the space in privacy.brbrbr*** Places to Go ***brbr** 10–15 Minutes **br- Bulleit Distilling Co. – Shelbyvillebr- Jeptha Creed Distillery – Shelbyvillebrbrbr** 30–40 Minutes **br- Lawrenceburg / Versailles / Frankfort / Louisvillebr- Four Roses Distillery – Lawrenceburgbr- Wild Turkey Distillery – Lawrenceburgbr- Woodford Reserve – Versaillesbr- Buffalo Trace – Frankfortbr- Castle & Key Distillery – Millville/Frankfortbr- Whiskey Thief Distilling Co. – Frankfortbr- Louisville Urban Bourbon Experiencebrbrbr** 35–40 minutes **br- Angel’s Envybr- Old Forester Distilling Co.br- Evan Williams Experiencebr- Rabbit Hole Distillerybr- Michter’s Fort Nelsonbrbrbr** 50–60 Minutes **br- Bardstown / Clermontbr- Jim Beam American Outpost – Clermontbr- Bardstown Bourbon Company – Bardstownbr- Heaven Hill Bourbon Experience – Bardstown

Bed

Bath

Sleeps

$418.49

/ Nightly

Private Vacation Home

Bourbon Trail Getaway ~ Hot Tub + Dogs Welcome + Game Room + Cornhole + KY Fun

Shelbyville, Kentucky, United States

Welcome to Bourbon Barrel Escape — your perfect launch pad for exploring Kentucky’s legendary Bourbon Trail! Located in charming Shelbyville, our stylish, fully furnished home is minutes from two local distilleries and less than an hour from 30+ more. Whether you’re sipping bourbon, soaking in the hot tub, or playing a game of pool, this retreat has everything you need for a fun and relaxing getaway.brbrTHE SPACE ~brbrUnwind in over 2,000 sq ft of comfort and style:brbr2 Master Suites with plush king beds, large smart TVs, and en-suite bathroomsbrbr2 Additional Bedrooms (1 queen with TV, 1 cozy queen room) near a full bathbrbrSpacious Living Room with comfy sectional, big-screen TV, and modern touchesbrbrGame Room with pool table + ping pong conversion, great for group funbrbrFully Equipped Kitchen stocked for home-cooked mealsbrbrOutdoor Patio with a hot tub, propane grill, cornhole boards & seatingbrbrAMENITIES YOU'LL LOVE ~brbrStarlink high-speed Wi-FibrbrHot tub under the starsbrbrPool table + ping pong conversionbrbrWasher & dryerbrbrSmart TVs in multiple roomsbrbrPlenty of parkingbrbrPets Allowed - $100 Fee (MAX 2) - See House Manual for pet guidelinesbrbrLOCATION HIGHLIGHTS ~brYou’re in the heart of Kentucky’s bourbon & horse country:brbr~Bulleit Distilling Co – 5 minbrbr~Jeptha Creed – 12 minbrbr~Buffalo Trace – 25 minbrbr~Churchill Downs – 40 minbrbr~Shelbyville Country Club – 12 minbrbr~Guist Creek Marina & Fishing – 6 minbrbr~Kentucky Kingdom Theme Park – 35 minbrbr~Louisville Airport – 35 min | Lexington Airport – 45 minbrbr~Guest AccessbrbrGuests enjoy full access to the home (excluding one locked supply closet).brbrADDITIONAL NOTES ~brFor local dining, events, and distillery tours, check out Visit Shelby KY Tourism. brbrWhether you're visiting for bourbon, horses, or quality time with family and friends — Bourbon Barrel Escape is the ideal home base for your Kentucky getaway!brbr(Shelby County Business License BU659)brbr**PLEASE NOTE THERE IS A $250 PET FEE CHARGED PER UNREPORTED PET**brbrPET POLICY: brWe welcome well-behaved pets at our property! To ensure a clean and comfortable experience for everyone, please note the following:brbrPet Fee: A non-refundable pet fee of $100 per stay will be charged. (MAX 2 PETS)brbrApproval Required: All pets must be disclosed and approved prior to check-in. Unauthorized pets will result in an additional $250 fee per pet.brbrCleanliness: Guests are responsible for cleaning up after their pets. (Indoor and Outdoor)brbrAny excessive messes (fur, stains, odor, etc.) or failure to clean up waste (indoors or outdoors) will result in additional cleaning charges starting at $100.brbrFurniture & Bedding: Pets are not allowed on beds or furniture unless covered with pet blankets (not provided).brbrCrating Recommended: If your pet will be left alone in the home, crating is encouraged for their safety and to prevent damage.brbrLet’s keep the space welcoming for all guests—thank you for respecting these guidelines!

Bed

Bath

Sleeps

$889.48

/ Nightly

Apartment

Bottled in Bond: Transportation available/Center of Bourbon Trail/ HGTV location

Shelbyville, Kentucky, United States

This swanky loft has so many WOW factors your eyes will be dancing! Enter the setting through the vintage revolving door or conveniently on the elevator and arrive on the scene of this character-packed accommodation. The owners have transformed this late 1800s space from what was once a clothing factory into what looks like a scene from a James Bond movie. You’ll enjoy features from its former glory such as original trusses, exposed brick and hardwood floors. And the updated details will blow your mind.brSEE BELOW REQUIREMENT FOR TRANSPORTATION PROMOTIONbrbrKitchen:br• Stunning state of the art kitchen that features quartz countertops and backlit white onyxbr• Commercial grade stove that doubles as an art piece and will make any cooking you do a culinary experiencebr• Plentiful sleek custom black and gold cabinetsbr• Premium appliancesbr• Linear Fireplace situated in custom lit tiled accent wallbrbrDining Area:br• Custom dining table made from wood from Jim Beam Distillery that’s been electrocuted (yes, you read that right) to feature a one-of-a-kind design!br• Seating for ten guests in trendy velvet chairsbrbrLiving Area:br• Custom built round gold leather couch surrounding a suspended fireplace and provides the perfect setting for conversation and cocktailsbr• Custom designed and built poker table that seats nine. br• Oversized plush couch in front of retractable projector for watching movies, games or your favorite showbr**Unfortunately, the Skee ball machine was recently broken. Because it is vintage, we have had a hard time repairing. Working our best to get it up and running.brbrbrCommon Area:br• The loft offers three additional living areas that can be converted into sleeping areas. These each include a Queen-sized Murphy Bed and are partitioned off by glass accordion doors, glass garage doors and custom velvet privacy curtains and are virtually soundproof. brbrPrivate King Suite: Enjoy our King Suite with its more masculine charm. It boasts br• Luxurious king-size platform bed with sleek yet super comfortable bedding, br• Smart TV br• Linear fireplace. br• Tremendous skylight br• Spa-like bathroom with double sinks, double rain showerhead and magnificant tub and private water closet.brbrbrPrivate Queen Suite: This room is full of whimsical touches that make it a guest favorite. br• Gold Canopy Bed br• A catamaran-like net that spans the entirety of the room reachable by a library ladder. Guests love to lay and stargaze through the expansive skylight just above it.br• Smart TVbr• Lavish bathroom with double vanity, rain and wall mount showerhead, shower bench and private water closet.brbrGuest Bathroom:br• Vintage trough sinkbr• Spectacular tile design br• Shower with two rain showerheads and plays off the curvature of the revolving door. brbrbrAdditional Features:brAbility to pipe music through the entire loft or individual rooms through Sonos App.brbrAdditional Notes:brThis loft is connected to our wedding venue, The Gatsby. If the event space is rented, you will hear some sounds of the adjoining festivities. However, event music must be off by 10pm and event guests are gone by 11pm. brbrGuests can bring their own poker supplies or, with ample notice, we can rent cards and chips for you for a $100 fee.brbrPRIVATE CHAUFFEURED TRANSPORTATION:brLet us navigate your perfect day and accommodate your transportation needs during your stay with us! Our experienced drivers have knowledge of the quickest and most beautiful ways to your distillery destinations plus the inside scoop on some local eateries. We’ll take the wheel while you enjoy the company of friends and family, and you'll arrive in style! The cost is $125 per person for the day.brbrPRIVATE CHEF OPTIONS AVAILABLEbrbrCome see why the space has been written about in so many magazines and publications. You will not be dissapointed.

Bed

Bath

Sleeps

$333.94

/ Nightly

Private Vacation Home

Historic home freshly renovated on the Bourbon Trail

Shelbyville, Kentucky, United States

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 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.

Bed

Bath

Sleeps

$312.57

/ Nightly

Cottage

2025 KY Derby 30 min Away ~ Bourbon Trail ~ Hot Tub

Shelbyville, Kentucky, United States

Step into the gorgeous and unique Shelbyville 3BR, 3Bath home, offering a perfect base for everyone coming to see the exciting saddle-horse farms, horse shows, or stopping by along the Bourbon Trail. If all Shelbyville attractions aren't enough for you, the private, in-house art gallery featuring the artwork of renowned local artists will leave you mesmerized. brbr✔ 3 Comfortable Bedroomsbr✔ Private Art Gallerybr✔ Gourmet Kitchenbr✔ Backyard br✔Smart TVsbr✔High-Speed Wi-Fi brbrLearn more below! brbrThe charming, spacious, and modern Victorian cottage was recently renovated and designed to provide a comfortable getaway for all visitors looking for a perfect Shelbyville stay. Its authentic setting mixes with outstanding attention to detail to offer the levels of relaxation and convenience that will leave you in awe as you visit the American Saddlebred Capital of the World and the distilleries along the famous Bourbon Trail. brbrAs you pass through the gorgeous hallway, you'll notice the beautiful furniture, tastefully picked décor, and stylish finishes enriched by plenty of natural light accenting the hard wood floors. Each room boasts a unique theme complemented by stunning local artwork. brbrYou'll surely notice that we turned the hallway into an awe-inspiring art gallery featuring many exciting works of local artists. Make sure to take some time out of your day to marvel at this lavish space. brbrThree highly comfortable bedrooms with ensuite bathrooms will provide all the relaxation you need after a long day of following the Bourbon Trail or visiting exciting saddle-horse farms and horse shows. brbrFinally, this fantastic oasis extends into an outdoor living space with cozy seating areas. Choose from the covered porch area and/or the private backyard where you can unwind and savor this beautiful home's breathtaking environment and arrangement. brbr★LIVING ROOM★brThe living room is perfect for enjoying fun and memorable moments after an eventful day. Find your place on the comfy sofa and enjoy the candle lighting ambiance from inside the fireplace and make sure you check out the gorgeous mural near the front door that pay tribute to Shelbyville's beautiful horses. brbr✔Chic Sofas with Pillowsbr✔Smart TVbr✔Record Playerbr✔Decorative Fireplacebr✔Comfy Sofa Chairsbr✔Stylish Coffee Tablesbr✔Reading Lamps brbr★ART GALLERY★brCelebrate renowned local artists' talent by stepping into the private art gallery. You'll get to enjoy the fantastic artwork without having to leave this stunning home. Below are the names of the featured artists. brbr✔Richard Sullivanbr✔ Kayla Weberbr✔ Andre Foremanbr✔ Sandy Kimura brbr★KITCHEN & DINING ★brCome to the fully equipped gourmet kitchen and use spacious granite countertops and ample cabinetry full of many state-of-the-art cooking appliances to create tasty homemade meals worthy of the most praised restaurants. brbr✔ Microwavebr✔ Stovebr✔ Ovenbr✔ Refrigerator/Freezerbr✔ Dishwasherbr✔ Coffee Makerbr✔ Toasterbr✔ Blenderbr✔ Sink - Hot & Cold Waterbr✔ Traysbr✔ Glassesbr✔ Silverwarebr✔ Pots & Pans brbrGet everyone in the kitchen to help with the cooking. Once the food is done, serve it on the inviting dining table and enjoy gourmet meals with your friends and family. brbr✔ Dining Table with Seating for 6br✔ Kitchen Island with Seating for 2 brbr★ SLEEPING ARRANGEMENTS - 3 BEDROOMS★brRetreat to these comfortable bedrooms, designed and furnished to provide you with all the rest needed after a day of adventuring throughout Shelbyville. brbr♛Master Bedroom: King Size-Bed, Smart TV (w/Queen Mattress and Built in Air Pump)br♛Bedroom 2: Queen Size-Bed (w/Twin Mattress and Built in Air Pump)br♛Bedroom 3: Queen Size-Bed brbr✔ Ensuite Bathroomsbr✔ Premium Pillows, Linens, and Sheetsbr✔Sound Machinesbr✔Ear Plugs br✔Decorative Fireplacesbr✔ Closets with Hangers and Shelvesbr✔Dressers with Spacious Drawersbr✔ Night Stands with Reading Lamps brbr***If more sleeping space is required, please note we have air mattresses available in 2 bedrooms found in the closets. brbr★ BATHROOMS★brEach of the three bedrooms offer an ensuite bathroom stocked with essential toiletries and fresh towels for maximum comfort and convenience. brbr✔ Walk-In Showerbr✔ Bathtub with a Showerbr✔ Vanity (Double in the Master Bath)br✔ Mirrorbr✔ Toiletbr✔ Towelsbr✔ Hair Dryerbr✔ Organic Toiletries brbr★ COVERED PORCH & BACKYARD★brSpend those warm summer nights under Kentucky's starry sky as you wander around the lush backyard or unwind in the covered porch. We promise that this fairy tale ambiance will keep you coming back. brbr✔Covered Porch w Seating Areas and privacy blinds and curtains brbr✔Spacious Backyard brbr✔BBQ Grill brbr✔Hot Tub brbrLook no further than this modern Victorian home for your memorable visit to Shelbyville. We are looking forward to you experiencing it in its complete comfort, style, and coziness. brbrThe home is exclusively yours, without interruption during your stay, so relax, unwind, and make yourself at home. brbrOther than the already mentioned amenities, our home also comes with: brbr✔ High-SpeedWi-Fibr✔ Air Conditioningbr✔ Air Purifiers in Each Roombr✔ Heatingbr✔ Washer/Dryerbr✔ Iron/Board brbrWe will be accessible 24/7 for our guests via phone, text, or the Airbnb app. brExpect a quick and prompt response. We give our guests space but are available for every inquiry. brbrContact us now so we can begin arranging your perfect vacation! brbrOverview brbrThe home is situated in Shelbyville, Kentucky, the town famous as an equestrian stronghold, home to over 80 saddle-horse farms. It is often referred to as the American Saddlebred Capital of the World. brHowever, you need not be a horse enthusiast to visit this delightful small town in Bluegrass Country, which has a lot to offer visitors. The city is close to Kentucky's famous Bourbon Trail, and you can visit two distilleries without leaving town. You can spend a lovely outdoor day enjoying a wine tasting at Talon Winery. If you want antiques and fine architecture, a visit to the Wakefield-Scearce Galleries is in order. No one should leave without experiencing genuine southern hospitality at the Claudia Sanders Dinner House. brbrHere are some places of interest you'll surely be looking to visit during your stay: brbr✔Stargazer Plaza (2 min away)br✔Wakefield-Scearce Galleries (3 min away)br✔Shelby County Community Theatre (3 min away)br✔Clear Creek Park Greenway(4 min away)br✔Mose Dale Park (5 min away)br✔Red Orchard Park (5 min away)br✔Cherokee Primitive Trail (6 min away)br✔Guist Creek Lake & Marina (8 min away)br✔Bulleit Distilling Co. Visitor Experience (9 min away)br✔Claudia Sanders Dinner House (9 min away)br✔Squire Boone Trail Loop (9 min away)br✔Jeptha Creed Distillery (9 min away)br✔Gallrein Farms (10 min away)br✔Talon Winery Shelbyville(12 min away)br✔Mulberry Orchard (15 min away) brbr***Distance times are calculated if traveling by car. brbrWe recommend that you arrive in a car as it will give you much freedom to explore and enjoy the beautiful town of Shelbyville. There is plenty of free street parking just outside the home. brbr★ COVID-19 SANITIZATION ★brHeath, safety, and well-being of our guests are of utmost importance. For this reason, we use a thorough cleaning process after each check-out. brbr★ NO PETS ALLOWED ★brWe love those little (and not so little) furry bundles of joy. Sadly, our home is not suitable to accommodate them. brbr★NO SMOKING INSIDE★brPlease refrain from smoking inside the home! Any smoking evidence will result in a fee for odor removal, duct, and furniture cleaning. brbr★NO PARTIES/EVENTS★brWe kindly ask you to treat our home as your own to preserve its pristine condition for future guests and your return visits. brbr★TRAIN TRACKS PROXIMITY★brPlease note that the freight train can occasionally pass along nearby tracks in this town. We have prepared ear plugs in all bedrooms to ensure that nothing will disturb your sleep. brbrThank you very much for your understanding.

3

Bed

3

Bath

9

Sleeps

$1024.61

/ Nightly

Private Vacation Home

Bridle & Bourbon Retreat-Horse Country Escape

Shelbyville, Kentucky, United States

Bridle & Bourbon Retreat offers a 3 bedroom, 3 bathroom stay in the heart of Shelbyville's horse and bourbon country. brThe main level features a trainquil primary suite with a king bed and ensuite bath, plus two guest bedrooms each with a queen bed. Gather with ease and unwind in comfort.brEnjoy soaking in the hot tubs, fireside evenings, and outdoor dining that includes a BBQ. Inside play a round of pool or get cozy in the theatre room for movie night. brConveniently located near Bulleit Co., Jeptha Creed, and Buffalo Trace distillieries, easy access to local horseback riding trails, equestrain events, and nearby golf. brGuests have access to the entire home and amenities excpet for the the lower level bedrooms which are not included in the reservation. Unauthorized occupancy into restricted areas will result in penalty fees. brWhether you’re unwinding or gathering with family and friends this home offers a welcoming atmosphere. Come experience refined comfort where horse country meets the Bourbon Trail. We look forward to hosting you at our place.

Bed

Bath

Sleeps

$371.47

/ Nightly

Private Vacation Home

6 Mi to Bourbon Trail: Group Estate on 20 Acres

Shelbyville, Kentucky, United States

Working Farm On-Site | 30 Mi to Louisville | 'The Brother Bear Lodge'brbrLooking for a serene home base for your Kentucky adventure This Shelbyville vacation rental is nestled among rolling hills and sprawling fields, offering a quiet retreat just miles from distilleries and horse farms. Wake up to peaceful views before heading out to savor the region's rich flavors at tasting rooms or feel the thrill of the track at Churchill Downs in Louisville. Southern charm is calling your name!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 queen bedbr- Bedroom 3: 1 queen bed br- Bedroom 4: 1 queen bed br- Bedroom 5: 1 king bed w/ box springbr- Additional Sleeping: 1 queen air mattressbrbrOUTDOOR LIVINGbr- Multi-level deck, gas grill, large yardbr- Walking paths, streams, bird watchingbrbrKITCHENbr- Fridge, stove, oven, dishwasher, microwave, cooking basicsbr- Drip coffee maker, paper towels/trash bagsbr- High chair, island, bar-top seatingbrbrINDOOR LIVINGbr- Smart TV, DVD player, 2 dedicated office spacesbr- 2 dining tables, fireplace, sunroombr- Books, board games, vaulted ceilingsbrbrACCESSIBILITYbr- Multi-level homebr- Stairs required to accessbr- Bedroom & bathroom on main floorbrbrPARKINGbr- Driveway (10 vehicles)br- Free street parkingbr- RV/trailer parking available on-sitebrbr-- THE LOCATION --brbr- 6 miles to The Bourbon Trailbr- 6 miles to Red Orchard Parkbr- 30 miles to Louisvillebr- 20 miles to Taylorsville Lake State Parkbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking br- NO PETS ALLOWEDbr- No events, parties, or large gatherings br- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATION:br- This multi-level home requires exterior stairs to accessbr- The homeowner lives on-site, in the basement unit, and may be present during your stay

Bed

Bath

Sleeps

$228.7

/ Nightly

Private Vacation Home

Quiet Downtown Maple Cottage Gem

Shelbyville, Kentucky, United States

Welcome to our charming Maple Cottage in the heart of a peaceful downtown neighborhood. This 3-bedroom, 1-bathroom home has undergone a complete remodel, ensuring a cozy and comfortable stay in Shelbyville. Whether you`re here for a weekend getaway or an extended stay, this cottage offers all the amenities you need. The fully fenced backyard offers privacy and space for relaxation and smores over the fire pit. Your Shelbyville adventure begins here!brbrnull.

1

Bath

6

Sleeps

Exceptional(6)

$551.54

/ Nightly

Private Vacation Home

Bourbon Trail Retreat . Sleeps 10 + Hot Tub. In the Heart of the Bourbon Trail

Shelbyville, Kentucky, United States

Get ready to relax in this 4-bedroom house in Shelbyville. Marvelous 3 king beds and 1 queen bed await guests in this nice property. With amenities like a washing machine, hair dryer, AC, heating, and WiFi, guests will have a tremendous stay. Our place will help you feel at home while you're traveling in Shelbyville.brbrIt is your gateway to the best of Kentucky Bourbon Country. Nestled between Louisville, Lexington, Lawrenceburg, and Frankfort, you'll be minutes from legendary distilleries like Jeptha Creed, Bulleit, Four Roses, Wild Turkey, and Buffalo Trace.brbrbrGather your crew and escape to The Bourbon Trail Retreat—a beautifully renovated 4-bedroom, 3-bath home perfectly nestled in the heart of Kentucky Bourbon Country. Whether you’re hopping distilleries with friends, reuniting with family, or planning a weekend to remember, this spacious and stylish retreat is your launchpad for adventure. Sip, relax, and make memories—just minutes from iconic stops like Jeptha Creed, Bulleit, Four Roses, and more!brbr4 Bedrooms • 5 Beds • Sleeps 10br3 Full BathroomsbrHot TubbrArcade Games + Kid-Friendly ToysbrFully Stocked Kitchen with CoffeebrWalkable to Downtown ShelbyvillebrbrThe SpacebrStep into Southern hospitality meets Bourbon trail lifestyle. This home welcomes you with a cozy front porch perfect for sipping cocktails or Kentucky sweet tea. Inside, a sunlit foyer and game-ready chess table greet you after a day of distillery tours or antique shopping in town.brbrMain Level Features:brSpacious living room w/ Smart TVbrbrFully equipped kitchen perfect for entertainingbrbrDining area for group mealsbrbrKing bedroom with plush beddingbrbrFull bathroom with walk-in showerbrbrIn-unit washer/dryerbrbrUpstairs Retreat:br3 spacious bedrooms with luxury linens & Smart TVsbrbrKing suite with en-suite bath & walk-in showerbrbrBedroom with two queen beds and cozy electric fireplacebrbrAdditional king bedroombrbrDeep soaking tub in hall bathbrbrBonus kitchenette with mini-fridge, cooktop, sink & countertop ovenbrbrGolden Tee & Pac-Man arcade gamesbrbrToy basket for younger guestsbrbrRelax in the hot tub under the stars after a full day on the trail.brbrBourbon Trail Access & AttractionsbrJust minutes to:brbrJeptha Creed Distillery (5 min)brBulleit Frontier Whiskey Experience (20 min)brFour Roses & Wild Turkey in Lawrenceburg (30 min)brBuffalo Trace Distillery in Frankfort (45 min)brDowntown Louisville’s Urban Bourbon Trail (40 min)brbrAlso near boutique shopping, local cafes, Shelbyville Fairgrounds, and scenic horse farms.brbrHouse RulesbrNo parties or eventsbrbrNo candles or open flamesbrbrRegistered guests onlybrbrHot tub note: Please notify host if water needs refilling—do not add water yourself.

Bed

Bath

Sleeps

$470.0

/ Nightly

Private Vacation Home

Hitching Post on the Bourbon Trl

Shelbyville, Kentucky, United States

The Hitching Post on the Bourbon Trail – Spacious Shelbyville retreat near charming downtown and walkable to the famous Horse Show. Minutes from Louisville and centrally located to top distilleries. Enjoy a man cave with poker, darts, shuffleboard and 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 and horse country!brbrOur home offers everything you need for a comfortable and memorable stay. The fully stocked kitchen includes all the essentials for cooking and dining, plus a central coffee station accessible to all guests—perfect for your morning brew. Step onto the screened-in porch to relax with coffee or unwind in the evening with a glass of bourbon. Downstairs, the man cave is a guest favorite—complete with shuffleboard, darts, poker table, WiFi-enabled big screen TV, mini fridge, and a bar area for ultimate game-day or movie-night fun.brbrEach bedroom is thoughtfully designed with the comfort of discerning travelers in mind. Enjoy brand-new WiFi-enabled smart TVs, luxury all-cotton linens, plush pillows, and high-quality bedding for a restful night’s sleep. Every bed features convenient charging outlets on both sides, making it easy to stay connected. Tastefully and stylishly decorated, each space blends warmth, elegance, and modern comfort—perfect for unwinding after a day of Bourbon Trail adventures or horse show excitement.brbrImportant Information for Your StaybrbrPlease note that our home shares a driveway with the neighbor on the right. We kindly ask that you do not block the driveway at any time and remain respectful of their access and privacy.brbrQuiet hours in Shelbyville, KY are from 11:00 PM to 7:00 AM. Out of respect for our neighbors and local ordinances, we ask that guests keep noise to a minimum during these hours—especially when enjoying outdoor spaces.brbrOur home is within walking distance to the world-famous Shelbyville Horse Show, located in the heart of the Saddlebred Capital of the World.brbrLooking for outdoor fun You'll be just minutes from several public golf courses including Wessinger Hills, Clear Creek, Persimmon Ridge, and Eagle Creek. Plus, Clear Creek Park—home to walking trails, playgrounds, and pickleball courts—is conveniently nearby for more active recreation.brbrWe hope you enjoy all that Shelbyville and the surrounding area have to offer!

Bed

Bath

Sleeps

$277.36

/ Nightly

Apartment

LeCoop Ultra Luxury 2 bed Loft on Bourbon Trail.Close to all distilleries

Shelbyville, Kentucky, United States

Ultra Luxury downtown 2 BR 2 Bath loft, spacious enough for 5 adults. Located in quaint Downtown Shelbyville, KY, you can experience it all while visiting: The Bourbon Trail, Churchill Downs, Keeneland, PGA or any weddings or events in the area. 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.brbrYou will be nestled in the center of a small town, but will have a hard time believing you're not in a big city with the unique urban vibe of Le Coop. The space was built in the late 1800s and details of its history can be told in the exposed trusses and brick and original decorative fireplace. The open concept living space features a sleek contemporary kitchen, ample plush seating for conversation or television, dining table for six and writer’s desk. Take in the views of Main Street from the expanse of windows that line the entirety of the front wall. Off the back of the loft, enjoy the screened in rooftop deck with seating for four.brbrThe Master Suite includes a gorgeous king-sized bed with elegant bedding and the en suite bathroom includes a tile shower and separate bathtub. brbrThe upstairs bedroom hosts a queen-sized bed and guests have a separate full bath downstairs with tub/shower combination.brbrA La Carte options available such as private chef, personalize horse tours and chauffeured bourbon tours.brbrCHAUFFEURED TRANSPORTATION:brLet us navigate your perfect day and accommodate your transportation needs during your stay with us! Our experienced drivers have knowledge of the quickest and most beautiful ways to your distillery destinations plus the inside scoop on some local eateries. We’ll take the wheel while you enjoy the company of friends and family and arrive safely and in style.brbrbr

2

Bed

2

Bath

5

Sleeps

Vacation Rentals By Owner In Shelbyville, KY

$424.84

$304.92

$834.75

$289.38

$821.34

$406.2

$243.47

$233.73

$829.21

$357.72

$418.49

$889.48

$333.94

$312.57

$1024.61

$371.47

$228.7

$551.54

$470.0

$277.36

Most popular vacation rentals in Shelbyville

$333.94

$478.53

$470.00

$467.46

$361.92

$357.72

$352.45

$243.19

$228.70

$233.73

Most Popular Cities in Kentucky