Vacation Rentals By Owner In Shelbyville, KY

The Horse & Hound is a one-of-a-kind, storybook farmhouse nestled on the grounds of Chickapoo Farm. With more than a century of history woven into its walls, this charming home invites you to slow down, breathe deeply, and step away from the noise of everyday life. Its elegant architectural details, captivating character, and sweeping pastoral landscape create a setting that feels both timeless and restorative. Here in Shelbyville, Kentucky, you’ll find it easy to fall back to a simpler rhythm—and feel the stress gently melt away.brbrTucked at the end of a long gravel drive, The Horse & Hound offers a peaceful retreat surrounded by countryside beauty. While it is one of two homes on the property, each is thoughtfully situated to provide a sense of privacy while still maintaining the warmth of a shared estate.brbrJust two miles down the same scenic road, you’ll also find our cozy cabin available for rent, comfortably accommodating up to six guests—perfect for friends or family who wish to stay nearby while enjoying their own private escape.brbrThe entire property is rich with character, where every detail has been carefully curated to make your stay feel welcoming and unforgettable. If you’re drawn to the serenity of nature paired with the charm of vintage-inspired furnishings, you’ll feel right at home here. And the views Truly breathtaking—whether you’re savoring a quiet morning coffee or watching the sun dip below the rolling hills.brbrSeveral renowned distilleries and wineries are just a short drive away, offering the perfect opportunity to explore the flavors of the region.

Country House

The Horse & Hound Bourbon Trail Retreat at Chickapoo Farm

Shelbyville, Kentucky, United States

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Exceptional(3)

$1272.77

Knobview Lodge sits on 30 private acres, sleeping 20+, it offers 6 king beds, 3 queen beds, and a twin with trundle. Enjoy the lower-level Bourbon Lounge with a Speakeasy Bar and 100-inch 4K TV, a new pathway to the Overlook, and a hot tub. Perfect for retreats, reunions, & family gatherings with rustic charm and modern comfort, plus easy access to the Bourbon Trail.brbrKnobview Lodge offers a luxurious and expansive retreat, perfect for group getaways and special events. The main primary bedroom on the first floor boasts a king bed for ultimate relaxation. Upstairs, the loft area includes two king beds with stunning views, while a bedroom suite provides even more sleeping options with two king beds and a twin trundle.brbrThe lower level, newly renovated in Fall 2024, is an entertainer’s dream. Known as the Bourbon Lounge, this space features a custom Speakeasy Bar ideal for bourbon tastings, along with access to the largest TV in any Kentucky Airbnb—a massive 100-inch 4K display for an unforgettable viewing experience. This level also offers multiple TVs, an arcade machine, and cozy seating, making it perfect for gatherings and special events. For added comfort, the lower level includes two queen Murphy beds, two private bedrooms with queen beds, and a spa-like bathroom equipped with dual shower heads.brbrAdditionally, a newly created pathway leads guests to the stunning Overlook area, where they can take in sweeping views spanning four separate counties in Kentucky. Knobview Lodge delivers the perfect blend of comfort, luxury, and entertainment, ensuring an unforgettable experience for large groups looking to relax and enjoy Kentucky’s finest scenery and offerings!brbrGuests will have full access to all 30 acres of Knobview Lodge, including private hiking trail for exploring the natural beauty of the property. Whether you`re enjoying the trail, relaxing by the lodge, or taking in the panoramic views, the entire space is yours to enjoy.brbrOur Bluegrass Stays Concierge Team is available to ensure your stay is seamless. We take care of every detail and are here for any questions or needs during your stay. Before your trip, we’ll work with you to ensure everything is prepared to your preferences, from special requests to tailored recommendations. brbrWhether it’s providing local insights or simply being on call for assistance, we’re committed to delivering a five-star experience.brbrAt Knobview Lodge, we prioritize your comfort and convenience, ensuring that every detail is taken care of for a seamless and enjoyable stay. The lodge offers high-speed Wi-Fi throughout the property, making it easy to stay connected. In the kitchen, you`ll find high-quality cookware, a coffee maker, and basic pantry essentials such as oil, salt, and sugar. Premium bedding and linens are provided, so you can rest easy in luxurious comfort.brbrFor relaxation, enjoy the hot tub or outdoor seating area, which offers stunning panoramic views. Inside, the living room is equipped with Smart TVs and streaming apps, along with a selection of board games and an inviting movie-watching space in the basement. We also provide a washer and dryer with detergent and supplies, so you can travel light.brbrAdditionally, the property features on-site parking for added convenience, as well as essential safety features, including smoke detectors, carbon monoxide detectors, and a first-aid kit.brbrFrom entertainment to essential amenities, Knobview Lodge is designed to offer everything you need for an unforgettable stay.brAs a reminder, our property is intended for quiet getaways and is not available for events or parties. To ensure a comfortable experience for all guests and to maintain the peaceful setting of the lodge, we kindly ask that you respect this policy during your stay.brbrIf you have any questions or need assistance, our team is happy to help. We appreciate your cooperation and look forward to providing you with a wonderful stay!

Cabin

Hillside Cabin w/ Slps 20+ 11BD 3BA Fireplace & Hot Tub

Shelbyville, Kentucky, United States

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Exceptional(9)

$165.09

Beautiful location on a working family farm. This cozy one bedroom studio is equipped with a comfortable queen bed, luxurious pillows and bedding. Twin rollaway is available if needed for children or additional guest. Night stand charging stations and lights, dinner table is large enough for 4 guest or to work remotely. Independent unlimited stable internet provided. Kitchen is stocked with a microwave, mini fridge/freezer, hot plate, electric skillet, pots/pans, crockpot and toaster. Also has a keurig coffee pot, variety of coffee pods, creamers and teas. These is also a 5 burner grill w side burner for outdoor cooking. brbrGuest can enjoy the fire pit, sitting down on the dock watching the sunset or roaming the farm interacting with the variety of sweet farm animals. There are horses, cows/calves, goats and chickens. No onsite fishing allowed. There is daily milking where you are welcome to observe, fresh milk/eggs available for additional cost to purchase directly from the farm. brYou won’t be disappointed with yourself stay. We always want guest to have the best experience possible so reach out! ****unit is within close proximity to main home. However, your privacy is respected during your stay.

Apartment

Shelbyville Farm studio close to hiking, horses, Kentucky derby and distillery’s

Shelbyville, Kentucky, United States

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Exceptional(7)

$1084.6

Tucked in the scenic 660 acres Stallard Springs Community, The Cabin+Bunkhouse is spacious, rustic-modern retreat for us to 23 guest on Bourbon Trail. Enjoy the blazing fiber internet, a pickle ball court, peaceful hiking trails, and fully equipped kitchen. all surrounded by Kentucky’s natural beauty. Just a short drive to Lexington or Louisville. It’s the perfect setting for families/retreat getaway seeking comfort, connection, and serenity.brbrThe spacebrCabin +Bunkhouse Sleeps 23 near Lex/Loubr@ Stallard Springs unfolds as a sanctuary of comfort and rustic elegance designed to accommodate up to 23 guest in a warm and inviting atmosphere.The space is thoughtfully appointed to blend seamlessly with its natural surroundings, offering expansive views of the prestigious Shelby County landscape.brbrUpon entering guest are greeted by spacious living area where plush seating set the stage for memorable evenings. The cabin’s interior is adorned with wood accents and local art, creating a sense of connection to the Kentucky Countryside.brbrEmbrace the local wildlife from our cozy cabin! Enjoy the unique charm of our decor, which includes tasteful and respectful displays of local wildlife, like a mounted deer head, fish & turkey. It's a nod to the natural beauty of our area and a conversation starter that adds to the authentic, rustic experience.brbrThe heart of the Cabin is the fully-equipped kitchen, where modern appliances and ample counter space invite guests to prepare and enjoy meals together. Adjacent to the kitchen, a large dining table serves as the perfect gathering spot for sharing and laughter over home cooked meals.brbrSleeping arrangements are generous and versatile, with 4 bedrooms & Bunkhouse we cater to both privacy comfort. Each room is furnished with quality bedding, ensuring a restful night’s sleep after a day of exploration. additional 2 full beds on screen porch. brbrOutdoors, the Cabin expansive deck overlooks the serene Stallard Springs Community, offering an idea setting for morning coffee or evening stargazing. Guest are encourage to explore the 660 acres of natural beauty that surround the cabin, whether through leisurely hikes, hikes near the tranquil creeks or simply enjoy the quietude of rural Kentucky.brbrWith the added convenience of high speed fiber internet, The Cabin @ Stallard Springs balances the allure of off-the-grid living with the necessities of the modern world, making it the ultimate retreat for those seeking both adventures and relaxation.brbrAs a reminder, our property is intended for a quite getaway and is NOT available for Parties or Events we have a strict No Party No Events policies & you will be ask to leave! Due to the fireplace being wood burning it is high risk and we ask you not use it because of liability! To ensure a comfortable experience for all guests and to maintain the peaceful setting of The Cabin, we kindly ask that you respect this policy during your stay. brbr Pets are not permitted in The Cabin & Bunkhouse due to hardwood floors. The Cabin has private septic system not public. please do not plush any paper or feminine products. Also do not pour any grease down drains in kitchen! If hot tub is used please leave cleaned or a fee will be charged! Blink Door Bell on Entrance to The Cabin which shows front porch n parking lot & Blink Door Bell on Entrance to Bunk House which shows Deck & parking! Thank youbrbrbrIf you have any questions or need any assistance, our team is happy to help. We appreciate your cooperation and look forward to providing you with a wonderful stay!brbrAlex DavidsonbrProperty Manager

Cabin

Cabin+Bunkhouse Sleeps 23 near Lex Lou Like New Spacious Modern Rustic Retreat

Shelbyville, Kentucky, United States

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$322.17

Welcome to Oak, the upper unit of The Copper & Oak — a thoughtfully restored 1909 home located in the heart of Shelbyville on the Bourbon Trail. Blending historic charm with modern style, this spacious two-bedroom, two-bath retreat offers the perfect balance of comfort and character.brbrStep into the bright, open living area featuring rich blue walls, warm wood floors, and an inviting mix of classic and modern décor. Kick back with a cocktail or local soda after a day of exploring distilleries, or gather for a movie night on the plush leather seating. The fully equipped kitchen is sleek and functional, ready for everything from morning coffee to full dinners around the chic dining table.brbrBoth bedrooms are thoughtfully designed with king beds, premium linens, and warm lighting for the ultimate in relaxation. The bathrooms blend vintage charm with modern luxury — walk-in tile showers, stylish vanities, and thoughtful details throughout.brbrFrom your doorstep, stroll through downtown Shelbyville’s boutiques, coffee shops, and restaurants — everything you need for a true local experience is within walking distance.brbrWhether you’re here for the Bourbon Trail, horse country adventures, or simply a weekend of rest and good company, the upper unit of The Copper & Oak offers timeless comfort with a modern twist.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

Private Vacation Home

Central Bourbon Trail Gem w/2 Kings

Shelbyville, Kentucky, United States

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Bath

Sleeps

Exceptional(47)

$123.7

Beautifully renovated condo duplex features 2 bedrooms / 2 bathrooms, light open floor plan, private entrance with parking at the door.. Just minutes from shopping, expressway, wineries, Bourbon Trail, horse farms and much more!! This lovely Condo is fully furnished including linens, towels, dishes and more! Work or travel, we welcome you to your home away from home! Located Close to shopping, farms, local interests and I64.. 25 minutes to Louisville, 45 minutes to Lexington.brbrAlthough we are pet lovers ourselves, out of respect for future guests we are unable to accommodate any pets. br

Condo

Horses, Bourbon and More .... Shelbyville Condo

Shelbyville, Kentucky, United States

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Bath

Sleeps

$405.65

Shuffleboard Table | Pet Friendly w/ Fee | EV Charger | Backyard Entertainment Area | Premium Mesh WiFi SystembrbrFind serenity in Shelbyville at this 3-bed, 2-bath vacation rental. This rural farmhouse offers everything you need for a memorable family stay or group getaway. The hot tub is perfect for soaking in after an adventurous day, and your fur pal will love the backyard. Visit the waterfall at Cove Spring Park or visit nearby distilleries on the Kentucky Bourbon Trail!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bed br- Bedroom 2: 1 king bed, 1 full bunk bedbr- Bedroom 3: 1 queen bed br- Additional Sleeping: 1 portable crib (w/ prior notice)brbrOUTDOOR LIVINGbr- Covered front porch w/ swing br- Gas grill br- Fire pit (wood provided)br- Picnic table br- Spacious fenced-in backyardbrbrINDOOR LIVINGbr- Smart TVs, shuffleboard table, record player br- Electric fireplace, breakfast bar, laptop-friendly workspacebr- Toys, books, board games, pet bedbr- En-suite bathroom, open layout brbrKITCHENbr- All major appliances, including dishwasher br- Cooking basics, dishware/flatware, spices br- Keurig coffee maker, complimentary coffee br- Blender, Crockpot, toasterbr- Trash bags/paper towelsbrbrGENERALbr- Free WiFi (premium mesh WiFi system, providing coverage to entire property)br- Central heating & air conditioning, ceiling fans br- Complimentary toiletries, hair dryerbr- Washer/dryer, iron/boardbr- Linens/towels br- Keyless entry brbrFAQbr- Pet fee (paid pre-trip)brbrACCESSIBILITYbr- Single-story home, 4 steps to enter brbrPARKINGbr- Driveway (6 vehicles) br- RV/trailer parking allowed on-sitebr- Level 2 EV chargerbrbr-- THE LOCATION --brbr- 19 miles to Cove Spring Park br- 24 miles to Woodford Reserve Distillery br- 38 miles to Louisville Mega Cavernbr- 42 miles to Kentucky Derby br- 39 miles to Louisville Muhammad Ali International Airportbrbr-- 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 smokingbr- Pet friendly w/ $50 fee (+ fees & taxes, 2 max)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story property requires 4 steps to accessbr- This home features a premium Amazon eero 7 mesh Wi-Fi 7 system, providing ultra-fast speeds up to 2.5 Gbps and whole-property coverage, including the outdoor patio and hot tub area. The mesh network automatically optimizes connections across 100+ devices for a seamless, high-speed experience anywhere on the property

Private Vacation Home

Shelbyville Farmhouse w/ Hot Tub, Fire Pit & Grill

Shelbyville, Kentucky, United States

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Bath

Sleeps

$122.76

Our lovely Condo features 2 bedrooms and 2 full baths – is located in a quite area of Shelbyville. Close to shopping, highway, bourbon distilleries, horse farms and much more!! Perfect for work or play! Inquire about extended stays.. brThis Open Floor Plan has 1st Floor Entry, front-door parking and 36” doors, low curb shower, LVT flooring, making it easily accessible. This home is fully furnished throughout, including a full kitchen with all appliances, dishes, drinkware and silverware, granite counter tops, washer and dryer, a wall-mounted flat-screen television, tasteful art, linens, towels and more.brLocated in a small condo community, with only 2 condo units per building. Parking at your door!

Condo

Your Kentucky Home Away From Home

Shelbyville, Kentucky, United States

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Shelbyville, Kentucky, United States

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Sleeps

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Bed

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Shelbyville, Kentucky, United States

Bed

Bath

Sleeps

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Bed

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