Vacation Rentals By Owner In Shelbyville, KY

$1504.98

Speakeasy, Hot Tub, Theater, Pickle Ball, Sleeps 20

Shelbyville, Kentucky, United States

Experience luxury at Oak & Ember Estate—an elegant 8-bedroom retreat (20 guest maximum) in the heart of bourbon country.brbrThis estate is situated on 5 private acres featuring designer rooms, private theater, hidden speakeasy, hot tub, and dual living spaces.brbrPerfect for bourbon enthusiasts, families, and discerning travelers.brbrIdeal location for distillery tours with exceptional entertainment spaces and thoughtful luxury touches throughout. Your unforgettable Kentucky experience awaits!brbrIndulge in the ultimate Kentucky luxury experience at Oak & Ember Estate, our prestigious 8-bedroom retreat accommodating up to 20 guests, strategically located in the heart of Bourbon country with seamless Derby access!brbrSet on 5 secluded acres with professionally designed themed rooms, private cinema, authentic hidden speakeasy for enjoying your bourbon purchases, relaxing hot tub, and sophisticated dual living spaces.brbrIdeal for bourbon enthusiasts, groups of friends exploring distilleries, discerning families, corporate retreats, and luxury travelers seeking an authentic Kentucky experience!brbr*LOCATION*brLouisville International Airport (SDF): 31.5 miles (30-35 min drive)brDowntown Louisville: 30 miles (30-40 min drive)brChurchill Downs (Kentucky Derby): 28 miles (35-40 min drive)brDowntown Shelbyville: Just a few minutes awaybrbr*BOURBON TRAIL EXPERIENCE*brOak & Ember Estate serves as the perfect home base for serious bourbon enthusiasts. After a day of tastings, return to comfort where you can continue your bourbon experience in your own authentic speakeasy.brbrNearby Distilleries:br- Jephtha Creed Distillery: 5.1 miles (10 min drive)br- Bulleit Distillery: 9.7 miles (15 min drive)br- Kentucky Artisan Distillery: 15.7 miles (30 min drive)br- Woodford Reserve Distillery: 36 miles (40 min drive)br- Wild Turkey Distillery: 32 miles (40 min drive)brbrCountless other world-class distilleries are within easy driving distance. The estate's central location makes this the ideal headquarters for your bourbon trail adventures.brbr*SOPHISTICATED ACCOMMODATIONS*brAttic Bedroom 1: Two Queen Beds, dedicated workspace with executive desk and chair, 55 Smart TV, en suite bathroom with dual vanities and rainfall showerbrbrSecond Floor Bedroom 2: King bed, 55 Smart TVbrbrSecond Floor Bedroom 3: King Bed, 55 Smart TVbrbrSecond Floor Bedroom 4: Queen Bed, 55 Smart TVbrbrSecond Floor Bedroom 5: Queen Bed, 55 Smart TV, BeanbagbrbrMain Level Master Bedroom 6: King bed with curated musical instrument displays, 55 Smart TV, dedicated workspace with executive desk and chair, private sitting area, ensuite bathroom with shower, soaking tub, and dual vanitiesbrbrMain Level Bedroom 7: King bed, 55 Smart TVbrbrBasement Bedroom 8: Two Queen Beds, 55 TVbrbrBasement Living Room: Convertible sofa bedbrbr*LUXURIOUS BATHROOMS*brEnjoy 4.5 exquisitely appointed bathrooms throughout the estate.brbrThe attic bathroom showcases a walk-in rainfall shower. The master bathroom features an indulgent soaking tub and separate standing shower. Both are enhanced with elegant double vanities.brbrTwo additional full bathrooms on the second floor and basement offer premium fixtures and designer touches that maintain the home's luxury aesthetic while providing ample facilities for larger groups.brbrA conveniently located half-bathroom on the main floor serves the common areas, ensuring comfort and privacy for all guests.brbr*GOURMET KITCHEN & ELEGANT DINING*brThe kitchen is a culinary sanctuary, perfect for preparing Derby Day appetizers or hosting a full bourbon-paired dinner for executives or family celebrations.brbrFeaturing premium appliances including a professional-grade oven, expansive refrigerator/freezer, dishwasher, icemaker, convenient pot filler, and microwave, you'll find everything needed to entertain with sophistication.brbrThe kitchen comes fully equipped with high-end cookware, elegant serving pieces, and all essentials including a Keurig coffee maker, Nespresso machine, French press, blender, toaster and more! We provide premium coffee, creamer, sugar, and select spices to enhance your stay.brbrGather at the stunning formal dining table with seating for 8, enjoy casual dining at the kitchen island with seating for 2, or savor al fresco meals at the outdoor dining table accommodating 10 guests. With multiple dining options, everyone can enjoy their preferred setting!brbr*REFINED LIVING SPACES*brUnwind in two distinct living areas, ideal for families, friends or corporate gatherings.brbrThe main floor living room offers sophisticated seating, curated décor, and a large 65 smart TV for evening entertainment.brbrThe lower level living area provides additional comfortable seating with entertainment options and a 65 TV, ensuring spacious accommodations for both shared experiences and private moments.brbr*EXCLUSIVE ENTERTAINMENT*brPrepare to be captivated by exceptional entertainment options!brbrDiscover the hidden door leading to an authentic speakeasy in the basement, featuring Kentucky bourbon-themed décor and a genuine saloon atmosphere—perfect for evening networking or family game nights.brbrExperience cinematic luxury in your private home theater with premium reclining seats, immersive surround sound, and a captivating big-screen experience—ideal for movie marathons or watching major sporting events.brbrMultiple smart TVs throughout the estate, along with curated board games and books, ensure entertainment options for executives and families alike.brbrExplore a custom-converted garage game room adjacent to the kitchen featuring golf putting simulation, billiards, classic arcade machines and more—creating memorable experiences for guests of all ages!brbr*SECRET SPEAKEASY AND PRIVATE CINEMA*brUncover exclusive hidden delights at Oak & Ember Estate!brbrStep through a concealed entrance to the authentic speakeasy, where you can unwind with your bourbon purchases in a genuine saloon atmosphere complete with a professional poker table—perfect for reminiscing about the day's distillery tours with friends or enjoying friendly competition.brbrIndulge in a captivating cinematic experience within your own private movie theater, meticulously designed for ultimate comfort and entertainment.brbrPrepare for an unparalleled stay filled with sophisticated surprises and exclusive moments.brbr*EXPANSIVE OUTDOOR SPACES*brEmbrace Kentucky's natural splendor on Oak & Ember Estate's sprawling 5-acre property.brbrThe manicured grounds offer premium outdoor seating perfect for morning coffee, evening cocktails, or business discussions. The propane grill provides an exceptional alfresco dining experience while enjoying the serene countryside setting.brbrRelax in the private hot tub under the stars after a day of bourbon trail exploration or business meetings.brbr*PREMIUM AMENITIES*br- High-speed WiFi ensures seamless connectivity throughout the propertybr- Comfortable seating throughout, designed with adult comfort in mindbr- Washer and dryer with premium laundry supplies provided for extended staysbr- Luxury linens and plush towels, upscale toiletries, and thoughtful touches create a five-star hotel experiencebr- Two electric fireplaces providing ambiance and comfort after a day of distillery toursbr- Multiple gathering spaces ideal for enjoying bourbon tastings with friendsbr- Spacious bathrooms with premium fixtures for ultimate comfortbr- Pack and play and high chair available for families traveling with little onesbr- Professional interior design throughout creating a cohesive luxury experiencebrbrWhat are you waiting for brbrReserve your stay at Oak & Ember Estate today and experience the perfect harmony of Kentucky heritage and contemporary elegance!

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Bath

Sleeps

$869.57

/ Nightly

Private Vacation Home

Shelby Stop on Bourbon Trail- HOT TUB and Pool. Pool is now Open

Shelbyville, Kentucky, United States

Welcome to The Shelby Stop where comfort & style awaits you!brbrThis 4 bedroom, 2.5 bath home offers space for everyone.br2 bedrooms are on the main floor; 1 of which is the luxury primary bedroom with en-suite bathroom.br1/2 bathroom just off the kitchen.brThe primary bedroom is a beautiful room with king size bed, luxury mattress, linens, large smart TV, sitting chair, & full size mirror. The attached en-suite bathroom is newly renovated in 2023brbrWe will be available by text message / phone during your stay. Additionally, we offer in-person support/maintenance when needed.brbrIt is a peaceful, residential city with a small-town feel, offering a mix of rural and suburban living. It's known for its quiet atmosphere and the rolling Kentucky countryside that surrounds the area. Shelbyville is also the Saddlebred Capital of the World due to the presence of numerous American Saddlebred horse farms. brbrWhile you’re staying here, this home is your private oasis. Guests will have full access and use of the house 24 hours a day.brbr Welcome to The Shelby Stop — Your Relaxing Kentucky Escape in the Heart of Horse & Bourbon Country brbrDiscover the perfect blend of peaceful countryside charm and modern comfort at The Shelby Stop, a spacious family retreat located in beautiful Shelbyville, Kentucky — just 35 minutes from Louisville and right along the famous Kentucky Bourbon Trail. Whether you’re planning a relaxing family getaway, a group trip, or a quiet work retreat, this home is designed to make your stay effortless and memorable.brbrbr The SpacebrbrStep inside to find an inviting open-concept layout filled with natural light and cozy touches throughout.brbr4 comfortable bedrooms with plush mattresses, quality linens, and thoughtful details to ensure a restful night’s sleep.brbr2.5 bathrooms stocked with soft towels, essentials, and plenty of space for families or groups.brbrFully equipped kitchen with modern appliances, cookware, spices, and a stocked coffee bar — perfect for cooking meals or enjoying slow Kentucky mornings.brbrSpacious living area with a smart TV, board games, and cozy seating — ideal for movie nights or rainy-day relaxation.brbrDedicated dining area where everyone can gather for meals, laughter, or a game night.brbrbr Outdoor OasisbrbrStep outside and take in the quiet country air. The outdoor spaces are what truly make The Shelby Stop special:brbrPrivate hot tub for unwinding under the starsbrbrOverground pool (seasonal) for family fun during warmer months. Pool is now open.brbrLarge deck and grill perfect for summer cookoutsbrbrFire pit area surrounded by seating — great for s’mores, stargazing, and long conversationsbrbrExpansive yard where kids (and adults) can play and explore safelybrbrbr Entertainment & ExtrasbrbrGame room with pool table, shuffleboard, and fun for all agesbrbrHigh-speed WiFi for streaming, remote work, or online classesbrbrWasher/dryer for extended stays or family travelbrbrFree parking on-site for multiple vehiclesbrbrbr Location HighlightsbrbrConveniently located in Shelbyville, you’re close to everything that makes Kentucky special:brbr Kentucky Horse Park & local horse farmsbrbr Kentucky Bourbon Trail favorites — Jeptha Creed, Bulleit, and more within 20 minutesbrbr ️ Outlet Shoppes of the Bluegrass (25 minutes away)brbr ️ Downtown Shelbyville (3 minutes) — restaurants, antique shops, and local charmbrbr Louisville (35 minutes) — Churchill Downs, museums, nightlife, and riverfrontbrbr ️ 45 mins to Keenelandbrbr ️Less than an hour to Lexington, Bardstown or Frankfort brbr ️ 1.5 hour to Mammoth Cave National Parkbrbr 1.5 hour to Red River Gorgebrbr Nearby accredited wineriesbrbrbr Guest ExperiencebrbrWe strive to make every stay seamless and welcoming. You’ll have:brbr24/7 responsive communication for any questions or requestsbrbrThoughtful touches throughout the home — from extra toiletries to local coffeebrbrSelf check-in for flexibility and privacybrbrWhether you’re here for a family gathering, bourbon adventure, wedding weekend, or quiet countryside retreat, The Shelby Stop offers everything you need to relax, reconnect, and make lasting memories.brbr Book your stay today and experience the best of Kentucky hospitality — comfort, charm, and calm all in one unforgettable home.brbrbrbrThis is a semi rural location. Most people drive here. There is electric vehicle charger in the garage for your convenience. Uber and Lyft are easily available. brbrPrior to your stay, we require you to sign & agree to our rental conditions.brbrPlease familiarize yourself with our Cancellation Policy prior to booking. We strictly adhere to our policies and always encourage guests to purchase optional travel insurance to cover unanticipated changes in travel plans. Hosts are not be responsible for issuing refunds due to changes made outside of the cancellation policy.brbrPlease supervise children around the pool, grill, fire pit, and hot tubbrDo not add add bubbles/salts/oils etc to hot tubbrBest to shower/wash off prior to and after hot tub usebrPlease use caution when using the hot tub if you have a heart condition, other medical issues, or are pregnant.brbr** hot tub to be used at your own risk **brbrIF the hot tub needs water added during your stay during winter months please DO NOT add water yourselves or use the hose. It can lead to burst pipes. Please let host know and we will get that taken care of.brbrCamera at the front door , front of garage and front of patio door for guest security.brbrThis is a semi rural property: you may see bugs, or other critters. However we do have the property treated regularly.

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$320.91

/ Nightly

Cottage

Beautiful restored Victorian farmhouse

Shelbyville, Kentucky, United States

Walking in is like going to grandmas house. 3 Large bedrooms, 4th bedroom is a loft that overlooks the livingroom. Great for the kiddos . Open concept kitchen, and living room with vaulted ceilings. Walk outside to a large deck overlooking large backyard, or sit on front porch and watch trains when they come by. Close to Bourbon trail and local horse farms. Convenient to Louisville and Lexington. Walking distance to downtown Shelbyville,where you can visit the antique shops or enjoy the local restaurants.

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Sleeps

$243.19

/ Nightly

Private Vacation Home

Brown Ave Bourbon Trail & Beds- Shelbyville, KY

Shelbyville, Kentucky, United States

Welcome to Brown Avenue Bourbon and Beds, a beautifully renovated 1950's charmer on the Bourbon Trail, near the Shelby County Fairgrounds & just minutes from downtown Shelbyville!brbrStart your day w/ coffee on the front porch swing, enjoy an afternoon snack on the back deck, cook dinner in the fully stocked kitchen & cozy up in the living room for movie night after a long day of exploring! brbrA short drive to Louisville, Lexington, Frankfort, KY Derby and Valhalla Golf Club! Sleeps 6brbrThe spacebr * Brown Ave is a single level 1250 sq ft, 3 bedroom, 2 bathroom home located on a quiet street in a desirable neighborhood perfectly suited for your getaway.brbr* Brown Ave is the perfect location when planning a full day of Kentucky exploring, bourbon tasting or enjoying the ponies! Not only is it a convenient location for travel, our home has hosted bridal showers, weddings, birthday parties and more! Our private back yard comes equipped with a gorgeous shade tree, privacy fencing, a large deck, outdoor furniture and a grill to meet your hosting needs. br br* The home is minutes away from distilleries, grocery stores, restaurants, parks, and the shops of downtown Shelbyville and a short drive to Louisville, Frankfort, Lexington & more.brbr* The welcoming living room features extra comfortable reclining seating, a Smart TV and electric fireplace (yes, it provides heat!).brbr* The dining room seats up to 8 people and is open to the fully equipped kitchen that features granite counters. The kitchen has stainless steel appliances, a gas stove, a keurig/drip coffee maker with all your coffee needs, silverware, plates, cups, bowls, knife set, can opener, measuring cups, mixing bowls, strainer, baking sheets, and pots/pans. The washer and dryer are located off the kitchen in the mudroom.brbr* There are three charming bedrooms and two full bathrooms. The first is a queen bedroom with an adjustable mattress, smart tv, and closet. The second is a queen bedroom with an adjustable mattress and vanity. The third bedroom enjoys a full size memory foam bed and closet.brbr* Welcome to the Saddlebred Capital of the World! The Brown Ave Bourbon and Beds is the perfect central location for your Kentucky getaway! It's close to all the amazing attractions in the area, situated between Lexington (Keeneland) and Louisville (Churchill Downs) / Valhalla Golf Club.brbrPlease make bourbon reservations in advance!brbr3 mins to Shelby County Fairgroundsbr3 mins to Downtown Shelbyvillebr10 mins to Talon Winerybr11 mins to Jeptha Creed Distillerybr12 mins to Bulliet Whiskeybr30 mins to Louisvillebr30 mins to Rising Sons Home Farm Winerybr35 mins to Buffalo Tracebr35 mins to Keenelandbr35 mins to Lover's Leap Winerybr35 mins to Castle & Key Distillerybr35 mins to Angels Envy Distillerybr40 mins to Four Rosesbr45 mins to Churchill Downsbr45 mins to Louisville Airportbr50 mins to Bardstownbr55 mins to Jim Beambr60 mins to Downtown Lexingtonbr15 mins to Valhalla Golf ClubbrbrThe home is professionally cleaned between every guest stay.brbrGuest accessbrA unique code will be provided the day before check in for the front door.brbrOther things to notebrThe home is located near a historical railroad that runs through Shelbyville and adjacent Kentucky towns. The train can be heard throughout the entire town during the day and occasionally during the night. brGuest accessbrThe outdoor shed and the lower part of the closet in the office are not for guest use and will be locked.

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Sleeps

$1056.24

/ Nightly

Apartment

Urban Loft 5,000 SqFt. Sleeps 17 Next to Frankfort Distilleries,PERFECT LOCATION

Shelbyville, Kentucky, United States

The biggest and best rental option in downtown Shelbyville, Urban Loft is the best place to stay in town. It’s an absolutely breathtaking space with enough sleeping space for well over a dozen guests to comfortably co-habitate, but the space is so absolutely picture perfect and secluded that you might have trouble coaxing all your traveling companions to ever leave. - Bourbon Review MagazinebrbrBreathtaking! Super exclusive high end downtown loft that has been at the center of many articles and television spots. Unlike any other space you will find at this price point! This location has been at the centerpiece of many television and print publications regionally. No expense has been spared converting this space into a luxurious 4 bedroom + 3 1/2 bed loft apartment centrally located between Lexington and Louisville KY. It's the perfect spot for the Bourbon trail and Kentucky Derby, not to mention the other events that make Kentucky such a special place to visit. This residence is situated close to several local eateries and bars. You will not be disappointed in reserving you stay.brbrYou’ll never believe what awaits you! The Grand Room hosts a huge custom dining table made with original wood from the building, a plush oversized sectional couch, and television and fireplace both situated in modern decorative tile. Turn the corner into a dream kitchen with expansive marble island with seating, locally-designed and crafted cabinets, double oven, five-burner gas stove, large pantry and cozy sitting area by the fireplace. Step outside onto the rooftop deck that offers additional dining and sitting areas, television and fireplace and Green Egg smoker for fun gatherings outside. You may never want to leave!brbrGrand Master Suite:brKing-sized Bed with Tufted headboardbrAccent Wall made from local bourbon barrel stavesbrModern Linear FireplacebrGlass shower room with spa-like bathtub insidebrGlass-top double vanitybrbrGuest Master Suite: brKing-sized Bed brPrivate bath with unique vanity crafted from local sawmill woodbrFloor to ceiling tile shower brTelevisionbrbrQueen Rooms One and Two:brEach room offers an exceptionally comfortable queen-sized bed and is adjoined by Jack and Jill bathroom with tub/shower combination.brbrTheater Room:brEnjoy this room for feature films of your choosing and also enjoy the custom mattress platform including two queen mattresses and one double mattress for sleeping.brbrMan Cave:brWatch games or shows on three televisions in this man cave that’s tucked toward the back of the home. This room features a bar, beer cooler, plush couch and chairs plus bar stools for additional seating. The focal point of this spot is the hanging vintage score board from one of the town’s local schools. brbrPlayroom: brBringing your family The kids are sure to love this playroom! Many guests enjoy the stage area for family talent shows or kid plays! It’s also stocked with plenty of toys, books, games and play school supplies for hours of enjoyment!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. $125 per person for the day

Bed

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$879.8

/ Nightly

Country House

Bridle & Bourbon Retreat ~ Sleeps 16 ~ Derby & Bourbon Trail Estate on 5 Acres

Shelbyville, Kentucky, United States

Welcome to Bridle & Bourbon Retreat nestled in the American Saddlebred Capital of the World. This spacious 5-bedroom, 3-bathroom home comfortably sleeps up to 16 guests, making it ideal for families, groups, and event travelers.brbrA private 5-acre country escape in Shelbyville, perfectly located for Kentucky Derby weekend and Bourbon Trail adventures. Just minutes from Bulleit Distilling Co. and Jeptha Creed Distillery, and a short drive to Buffalo Trace Distillery.brBridle & Bourbon Retreat offers the perfect home base for exploring the Bourbon Trail, horseback riding along local trails, attending equestrian shows, or enjoying a round of golf.brbrAfter a full day of adventure, unwind beneath the stars with a relaxing soak in one of the private hot tubs, gather with friends, and enjoy the peaceful beauty of Kentucky’s countryside.

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$145.45

/ Nightly

Apartment

Downtown Main Street One-Bedroom Suite w/ Hi-Speed Wifi

Shelbyville, Kentucky, United States

Stay @ The Stables Suite, your home away from home in the heart of the city. Our cozy 1 bedroom suite offers everything you need for a comfortable and convenient stay. With a kitchen, full bathroom, spacious living room, and a comfortable queen-size bed in the bedroom, you will have all the comforts of home at your disposal. Whether you're here for business or leisure, our suite provides the perfect accommodation for a great stay. Book with us now and experience the best of city living at The Stables Suite. Note: Access to the space is through the ground floor of The Stables Shared Workspace. Located on the 2nd level, the suite can be accessed via steps, giving you a sense of privacy and exclusivity.

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$1820.91

/ Nightly

Private Vacation Home

Heated Pool~2 hottubs~ Barrel Sauna~Theatre~Arcade~Game Room~PS5 Lounge~ 16 BEDS

Shelbyville, Kentucky, United States

EMINENCE DOWNS: KENTUCKY LUXURY REIMAGINEDbrbrEminence Downs invites you to experience Kentucky’s finest traditions—reimagined for the modern traveler. Set on the lush, rolling countryside of Shelbyville, this elegant estate blends the timeless sophistication of a thoroughbred farm with the effortless style of a Ralph Lauren editorial. Think leather and linen, plaid and polish, and the clinking of bourbon glasses by the fire. brbrELIMINATING THE TRAVEL BOTTLENECKSbrbrWe have meticulously curated this estate to handle large groups effortlessly. Whether you are here for a corporate retreat, a multi-family reunion, or a wedding party, our high-capacity infrastructure ensures a seamless stay. brbrZERO-BOTTLENECK KITCHENbrbr-- Newly remodeled and fully equipped for 21 guests. -- Features two dishwashers in the main kitchen and a third dishwasher in the kitchenette (coming soon). -- An abundance of utensils and cookware is provided for your largest feasts.brbrDUAL LAUNDRY SUITEbrbr-- Two washers and two dryers allow your group to refresh towels and clothing in half the time. No more waiting in line for the dryer.brbrHIGH-SPEED CONNECTIVITYbrbr-- Stay connected with high-speed Starlink Internet, perfect for remote work, large video conferences, or seamless 4K streaming.brbrADULT COMFORT: 16 BEDS (ZERO BUNKS)brbrPrioritizing rest and quality, our estate features 16 actual beds—with a strict no bunk beds policy—to ensure a premium experience for up to 21 guests. For larger groups, we offer additional flexibility with numerous oversized couches and designer sofas positioned throughout the common areas of the house. brbrTraveling with a larger party Please enquire with the host for more details on how we can best accommodate your specific group size and needsbrbrQUICK-REFERENCE BEDDING LISTbrbr-- Primary Suite (Bedroom 1): 1 King Bed + 2 Twin Bedsbr-- Guest Suite (Bedroom 2): 1 King Bed + 1 Twin Bed br-- Deluxe King (Bedroom 3): 1 King Bedbr-- Deluxe King (Bedroom 4): 1 King Bed br-- Queen Suite (Bedroom 5): 1 Queen Bed + 1 Twin Bedbr-- Twin Suite (Bedroom 6): 2 Twin Bedsbr-- Cozy Single (Bedroom 7): 1 Twin Bedbr-- The Loft: 4 Twin Bedsbrbr-- TOTAL BED COUNT: 16 High-Comfort Beds (including premium trundles)brbr -- EXTRA CAPACITY: Multiple designer sofas and oversized couches located throughout the estate for flexible guest arrangements.brbrTHE GLAMOUR SUITEbrbr-- A dedicated, mirrored suite designed specifically for the ladies in your group. This professionally styled space offers plenty of room for hair, makeup, and dressing for the Derby or a wedding in total comfort. brbrTHE ENTERTAINMENT WINGbrbrThe lower level and bonus rooms are a private playground for all ages:brbr-- PRIVATE CINEMA: Comfortable seating for an authentic movie-theater experience.br -- GAMING LOUNGE: A professional Pool table, Shuffleboard, Dart board and Retro Arcade cabinets. br-- INTERACTIVE FUN: Host a Karaoke night, a Poker tournament, or choose from our extensive collection of board games. br-- PS5 LOUNGE: A dedicated retreat featuring a PlayStation 5 with two DualSense wireless controllers. br-- TABLE TENNIS: A full-size table for friendly competition.brbrbrOUTDOOR RESORT LIVINGbrbr-- THE WATER: A private Heated Pool (seasonal) with a safe, electronic autocover for peace of mind (coming soon). br-- THE SPA: Two private hot tubs set under a designer pergola.br -- WELLNESS: Our Barrel Sauna (coming soon) and secondary firepit offer the ultimate spa day at home. br-- THE FIRE: Choose between the indoor propane fireplace, the outdoor propane fireplace, or the classic wood-burning firepit (coming soon).br -- DINING: Expansive indoor and outdoor dining areas to accommodate the whole group for sunset meals alfresco.brbrbrLOCATION: THE HEART OF BLUEGRASSbrbrLocated in Shelbyville, the Saddlebred Capital of the World, you are minutes away from the best of Kentucky:brbr-- BOURBON TRAIL: Bulleit Distilling Co. and Jeptha Creed are right here, with Buffalo Trace and Woodford Reserve a short drive away.br -- HORSE COUNTRY: Schedule a private tour of a historic American Saddlebred farm. br-- SHOPPING: Visit the Outlet Shoppes of the Bluegrass or the boutiques of Historic Downtown Shelbyville.brbrGUEST RULES, SAFETY & AMENITIES br--No Smoking Inside: $1000 fine for violations brbr--Intimate Parties are allowed, but different rates and rules apply. Please contact us in advance.brbr--Parking: Ample space available.brbr--Pool & Spa: For your safety, food and glass are strictly prohibited in the water. We recommend guests refrain from hot tub use if pregnant or consuming alcohol. Use of all amenities is at your own risk.brbr--Pool Heating: Optional heating is available to enhance your stay. Because rates vary by season, please enquire for a current quote. Heating is required for the full duration of your stay and should be requested in advance to ensure the pool is ready for your arrivalbrbr--Security: To ensure total peace of mind, the manor’s exterior is monitored by a Ring doorbell and floodlight camera( above garage). For guest safety, a camera also monitors the pool perimeter, though it is never used to observe guests directly and is not actively monitored during your stay. All recordings are securely stored and automatically deleted post-departure in strict adherence to platform privacy policies and applicablel local , state and federal regulations. brbr--Travel Protection: We highly recommend purchasing travel insurance to protect against unforeseen weather or changes in plans.brbr--The Setting: As we are nestled in the beautiful Kentucky countryside, you may encounter local wildlife or insects. We provide regular professional pest control to maintain your comfort.brbr--This property has special local compliance requirements which include a signed rental agreement, ID verification, and a security hold of $1000 (which is not a traditional security deposit, just a pending transaction). As an optional alternative to the security hold, you may opt in to purchase a non-refundable damage waiver provided by a third-party insurance company. The optional damage waiver is $37 for stays up to 10 nights, with an additional $2 per day for stays longer than 10 nights. Damage waiver purchases are optional.

7

Bed

4

Bath

25

Sleeps

$4547.4

/ Nightly

Private Vacation Home

The Gatsby and adjoining ceilings

Shelbyville, Kentucky, United States

Our Gatsby Event Space offers the perfect melding of Modern Romance and Roaring Design. As the name suggests, you'll find yourself in the midst of what feels like the roaring 20's, but the adjoining loft and our other accommodations boast state-of-the-art design details today's imagination might only dream of. Have your event at the 10,000 soft. Gatsby and enjoy onsite overnight accommodations at the adjoining ultra modern/luxury loft apartment.

5

Bed

3

Bath

10

Sleeps

$148.8

/ Nightly

Private Vacation Home

Cozy 1-bedroom house in marvelous Shelbyville with AC, Lake view, Fire Pit

Shelbyville, Kentucky, United States

Escape to this peaceful lakeside retreat located on beautiful Guist Creek Lake in Shelbyville, KY — the perfect getaway for relaxing with family and friends. Featuring an inviting open-concept kitchen, dining, and living area, this cozy home is designed for comfort, connection, and unforgettable memories.brbrThe spacious master bedroom offers a comfortable queen-size bed, generous closet space, and a private full bathroom for added convenience. A second guest room doubles as an office space and includes a convertible twin sofa bed, making it ideal for extra guests or remote work stays.brbrStep outside to enjoy stunning lake views from the covered deck, perfect for morning coffee or evening sunsets. Take a short walk to the back of the property and down the stairs to a peaceful shaded area overlooking the water — and don’t forget to bring your kayaks for even more lakeside fun!brbrThe spacebrConveniently located between Louisville, Lexington, and Cincinnati, this home places some of Kentucky’s best attractions, dining, shopping, and entertainment within easy reach.brbrPrefer to stay in Spend your evenings grilling outdoors, relaxing around the fire pit overlooking the lake, playing games with loved ones, or streaming your favorite movies on the 50” Smart TV.brbrPlanning to explore the Bourbon Trail The famous Bulleit Distillery is just a short drive away, along with several local restaurants, shops, and outdoor attractions nearby.brbrFor even more local recommendations and hidden gems, be sure to check out our Guidebook included in your arrival information.

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$233.14

/ Nightly

Country House

Peace and Quiet Close to Louisville - 80+ Acres

Shelbyville, Kentucky, United States

Welcome to Farmhouse Hannah, your serene retreat 20 minutes to downtown Louisville and 5 minutes from the Outlet Shoppes of the Bluegrass! This charming farmhouse offers a perfect blend of rustic charm and modern comfort, making it the ideal destination for a peaceful getaway.brbrAccommodation:brFarmhouse Hannah boasts three cozy bedrooms, a spacious living area with a fireplace, and a fully equipped kitchen. Whether you're looking for a family escape, a romantic weekend, or a gathering with friends, our farmhouse provides the perfect setting.brbrNotable Amenities:brFully equipped kitchen with modern appliances.brInviting outdoor patio for al fresco dining.brA picturesque garden with ample seating for relaxation and stargazing.brA warm and inviting living room with a fireplace for those cozy evenings.brFree Wi-Fi and a flat-screen TV for entertainment.brAir hockey table and pop-a-shot basketball for some friendly competition.brTwo private ponds for fishing, offering tranquil moments by the water.brGarage parking available for your convenience.brbrLocal Attractions:brExplore the historic charm of Shelbyville with its quaint downtown area, unique boutiques, and delicious dining options. You're also just a short drive away from the renowned Kentucky Bourbon Trail, where you can tour distilleries and savor the finest bourbons. Here are some more local attractions:brbrShelby County History Museum: Explore the local history and heritage of Shelby County through exhibits and artifacts.brbrClaudia Sanders Dinner House: Visit this famous restaurant known for its delicious fried chicken and Southern comfort food.brbrGallrein Farms: Enjoy a family-friendly farm experience with seasonal activities like pumpkin picking and a corn maze.brbrClear Creek Park: A beautiful park with walking trails, a lake, and picnic areas, offering a peaceful outdoor escape.brbrJeptha Creed Distillery: Take a distillery tour and sample craft spirits, including bourbon and vodka.brbrTalon Winery & Vineyards: Savor local wines and enjoy a vineyard tour in a scenic setting.brbrGuist Creek Marina: Rent a boat, go fishing, or simply enjoy the lakeside scenery at Guist Creek Lake.brbrThe Outlet Shoppes of the Bluegrass: Shop for deals at this outlet mall featuring a variety of stores.brbrKentucky Vietnam Veterans Memorial: Pay your respects at this touching memorial dedicated to Vietnam War veterans.brbrDowntown Louisville Attractions:brbrLouisville Mega Cavern: Venture into an underground adventure with zip lines and tram tours.brLouisville Waterfront Park: Enjoy scenic views and recreational activities along the Ohio River.brMuhammad Ali Center: Explore the life and legacy of the legendary boxer Muhammad Ali.brLouisville Slugger Museum & Factory: Discover the history of the iconic baseball bat.brFrazier History Museum: Learn about American history, including the Lewis and Clark expedition.brThe Kentucky Derby: Experience the excitement of The Most Exciting Two Minutes in Sports at Churchill Downs, which is famous for hosting the Kentucky Derby.brbrThe Bourbon Trail: Embark on the Kentucky Bourbon Trail, which includes tours and tastings at various bourbon distilleries in the area, offering an authentic bourbon experience.brbrThese attractions offer a diverse range of experiences, from history and outdoor activities to culinary delights and world-famous events like the Kentucky Derby and the Bourbon Trail, all within a short drive of Shelbyville, Kentucky.brbrOutdoor Activities:brFor nature enthusiasts, Farmhouse Hannah is surrounded by scenic landscapes and offers opportunities for, bird-watching, fishing, and relaxation. Explore nearby parks and trails, or simply enjoy the tranquility of our countryside location.brbr*A Note About Our Natural SurroundingsbrOur property is nestled in a beautiful rural farm setting where insects are simply part of the charm — we treat regularly and do our best to keep them at bay, but nature will be nature! Please note that we do not offer discounts or refunds for minor insect encounters.brbr*The fireplace is non-functioning, no wood is provided because the fireplace is for looks only.brbrBook Your Stay:brEscape the hustle and bustle of city life and unwind at Farmhouse Hannah. Whether you're seeking relaxation, adventure, or a bit of both, our farmhouse is the perfect base for your Kentucky experience. Book your stay today and discover the beauty of Shelbyville from the comfort of our charming retreat. Plus, enjoy the added convenience of garage parking during your visit.brbrRENTAL AGREEMENT/REQUEST FOR CONTACT INFORMATION: In accordance with booking platform policy and local regulations, guests are required to provide contact information and sign all Rental Agreements within 24 hours of booking. If guests do not complete or refuse to sign the rental agreement, host reserves the right to cancel the reservation without penalty and the cancellation policy will still apply.brbrWIFI: All guests will be asked to enter email and phone number in order to access the free WiFi at this location. Contact confirmation is optional. In accordance with booking platform policy, we use apps to facilitate our guest experience and these apps may request contact information before, during, and after your confirmed stay.brbrKENTUCKY DERBY: All Kentucky Derby week/weekend reservations are non refundable, regardless of whether or not a rental agreement has been signed.brbrRECORDING DEVICES: Recording devices are located on the exterior of the property. Devices record audio and video and recordings are triggered by motion. Devices will be active during guests stay. Recording devices only capture views of the exterior. Guest safety and privacy are top priorities. These recording devices exist solely for the safety and security of our great guests!brbrNO SMOKING: Absolutely no smoking or vaping inside the homebrbrCHECK IN: Contactless check in is available until 10 pm EST via keypad. Any guests planning to check in after 10 pm EST must notify the host in writing prior to 10 pm to make accommodations for after hours check in. The host may not be available to assist with any check in issues between 10 pm and 9 am EST brbrNUMBER OF GUESTS WE HOST: We expect to only host the number of people on your reservation only. For insurance and safety purposes, please make sure your reservation reflects the accurate number of people. Otherwise you may be subject to a fee and you may be asked to leave. brbrNOISE LEVELS: Please be mindful of noise levels at all times and be respectful of neighbors by adhering to the quiet hours.brbrPARTIES/EVENTS: Absolutely no parties or events are allowed without written approval from the host prior to check in.

Bed

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$1486.0

/ Nightly

Private Vacation Home

Speakeasy w/heated pool, hot tub, pond, game room

Shelbyville, Kentucky, United States

Discover the ultimate adult-only retreat at our secluded Private Bourbon Trail Speakeasy! Nestled in the heart of Shelbyville, this property is a luxurious launching point for various Bourbon Trail tours. brbrEnter our thoughtfully renovated home, inspired by a stylish dark academia speakeasy theme. Here, you`ll find ample space for relaxation and entertainment in the opulent 8-bedroom, 8-bathroom home comfortably sleeping 16 guests. brbrDesigned with an open-floor concept, the central hub of our home blends elegance and comfort. Enjoy the coziness of the gas fireplace, lounge on the leather sofas while discussing upcoming adventures, or, perhaps, lose yourself in a good book with enchanting views as your backdrop.brbrEmbrace your culinary skills in our well-equipped kitchen, featuring high-end appliances, ample counter space, and an oversized fridge and freezer. Two dining tables and additional bar seating facilitate shared dining experiences in the comfort of home.brbrStep outside to awash in the serenity of 14 fenced acres featuring a shimmering 5-acre pond. Lounge on the expansive sun-drenched deck, swim in the dazzling pool or treat yourself to a spa-like experience in one of the two hot tubs. Here, numerous secluded corners set the stage for relaxation, sunbathing, fishing, and stargazing.brbrThe 4 detached, en-suite cabins provide additional privacy and breathtaking views of nature. Each comes with a coffee bar, mini fridge, and patio. brbrNight owls will appreciate the lighted walkways to the fire pit where the only disturbance will be the rustling of leaves in the nocturnal breeze. brbrKeep the fun going in the Game Barn, housing a game room and a cigar room (the only designated smoking area). Challenge your friends to a round of pool, ping pong, foosball, darts, shuffleboard, or golf stimulated games while sipping on your favorite drinks.brbrAt the end of the day, retire to one of the ultra-comfortable bedrooms, each furnished with premium linens, smart TVs, and high-speed chargers. The main bedroom pampers with a dedicated coffee nook, a spacious bathroom with a copper tub, and rain shower. brbrEnjoy a worry-free stay with essential toiletries stocked in all 8 bathrooms, 7 of which offer full showers and bidets.brbrThe property further offers air conditioning, heating, free parking, two EV chargers, and complimentary Wi-Fi. A strict emphasis on cleanliness ensures you a healthy, safe, and comfortable stay.brbrBook now and experience the dreamy blend of luxury and privacy at our charming speakeasy - we can`t wait to welcome you!brbr*RUFUNDS* Any interval between April to September or for major holidays attracts a full refund for cancellations made 30 days prior to arrival date and 50% refunded if cancelled 14 days prior to arrival and no refund if cancel less than 14 days. brbr*For any rare mechanical failures in our amenities, we will seek immediate technical help but cannot offer refunds or compensation.br★ENJOY★ You are on vacation, please enjoy your stay. PLEASE TREAT OUR PROPERTY AS YOUR OWN!br*Our home is set up for adults, do not recommend children here. If you bring any children, you will be responsible for their safety, for any damages that occur, and for anything that is stolen. br*Please park in the different driveway locations at the front of each building. Stay off the grass!br*No unregistered guests or visitors are allowed.brbr1. NO Parties/PET: Please kindly note that neither pets nor parties are allowed on the property. Either will results in a $500 fine Plus any damages that occur. If you have a service animal, you must disclose this information prior to booking. You are also responsible for any damages. If there is evidence of a pet being inside the home that was not given permission or damage done by a pet, you will be charged extra $500 for the cleaning that will be necessary. You could also be asked to leave the premises without refund due to breaking the rules.brbr2. NO SMOKING: Apart from the designated cigar room, smoking indoors or near the entryways will incur a $500 cleaning and Ozone fee. This includes but not limited to Vaping, cigarettes, marijuana, or any other form of smoking. If you smoke outside, please clean up after yourself. brbr3. Hot Tub Rules: brMust be 18yo to enter hot tub. Must shower prior to entering the hot tub. No sunscreen, self tanner, or any creams can be on your body when you enter the hot tub. No glass containers.brConsult your physician before entering hot tub. NO lifeguard on duty. Enter at your own risk. brCover hot tub when done, attach clips. Failure to follow these rules will results in extra $200 cleaning fee. BE AWARE: There are no extra safetly measures in place for children at this property since we do not recommend children at this property. You would be responsible for your childrens safety reguarding all bodies of water at this location.brbr4. POOL Rules:brMust be 18yo to swim alone. No glass containers near or in the pool. NO DIVING, the pool is only 5ft deep. BE AWARE: There are no extra safetly measures in place for children at this property since we do not recommend children at this property. You would be responsible for your childrens safety reguarding all bodies of water at this location. NO lifeguard on duty. Enter at your own riskbrbr5: POND, OPEN BODY OF WATERbrNO DIVING. NO HUNTING the animals, Fishing is permitted, catch and release required! SWIM at your own risk! No LIFEGUARD. BE AWARE: There are no extra safetly measures in place for children at this property since we do not recommend children at this property. You would be responsible for your childrens safety reguarding all bodies of water at this locationbrbr6. NO Glitter/No Dye: Glitter is almost impossible to remove and will results in an extra $750 cleaning fee. Do not use any temporary or permanent hair dye or other dye products in the rental. Evidence of dye will results in $500 fine or more due to damage to sink, floors, carpets, etc. brbr7: DO NOT STEAL THE DECOR: we have inventory of all the unique items that are in our home. If you steal any of these items, you will be responsible for the price of the item and a $1000 fee for restocking.brbrThe Primary contact is legally and financially responsible to ensure all guests and anyone who enters the home during their stay abide by these rules. brbr*There are outside cameras, none inside the house and none are facing the hot tubs to give privacy. There are 2 ring flood lights facing the driveways and road. The ring doorbell for the side entry. A ring camera facing the driveway/gate. A ring camera facing the front door and one facing the side fence/gate. There is a camera facing the pool, one facing the pond, and one facing the back sliding glass door that are all on the back deck. NONE FACING THE HOT TUB. There are ring cameras facing the entry to the game barn/side fence/gate, one that sees all the cabins entryways, and one facing the firepit/pond. These are all on the game barn, NONE FACING THE HOT TUB!. Many of these locations are for insurance purposes. The cameras are in place to protect you and us. Again, there are no cameras inside the house or facing the hot tubs. br*Please report any damages, breakages, or malfunctioning equipment immediately so that we may repair or replace the item. We understand that accidents happening but need to be notified. br*Please DO NOT Move furniture from one room to another to avoid any damages or breakages.br*No Eating or drinking in the Bedrooms.br*Please do not overstuff the washer/Dryer. If clothes are full of mud, please wash off outside first. Clean out dryer lint after each load. Please reuse pool towels to decrease water usage.br*Please turn off electronics and lock all doors every time you leave the housebr*NO HUNTING ON THE PROPERTY!br*We are not responsible for any injuries or accidents that happen on the property. You know you are in the woods with other wildlife, bugs, and critters, please respect that. Your safety is your own responsibility. Please act accordingly.brbr**You DO NOT have to clean the house or strip the beds. Just take out the trash.brPlease shut off all electrics and lock the doors when you exit the property.brPlease be sure all fires are completely out each night and before you leave.

Bed

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$478.53

/ Nightly

Private Vacation Home

Bourbon Trail~Hot Tub~Sleeps 10~Firepit~Gameroom

Shelbyville, Kentucky, United States

Unwind in the hot tub beneath glowing string lights, sip bourbon around the fire pit, and gather in your own private speakeasy—this charming Shelbyville retreat is made for unforgettable group getaways just minutes from the Bourbon Trail.brbrThis beautifully restored historic home blends classic charm with modern comfort, giving your group plenty of space to relax, connect, and enjoy every moment. Whether you're here for a bourbon tour, a weekend getaway with friends, or a family trip, the home is set up to make your stay effortless and memorable.brbrWHAT YOU'LL LOVE:br★ Private speakeasy lounge perfect for bourbon tastings, poker nights, or unwinding after a day outbr★ Covered hot tub for year-round relaxation, rain or shinebr★ Cozy fire pit area with Adirondack chairs and string lights—ideal for evening drinks and conversationbr★ Game room with pool table for friendly competition and group funbr★ Spacious living areas designed for gathering, dining, and making memoriesbr★ Fully stocked kitchen for cooking at home or hosting group mealsbr★ 2 King Beds br★ 2 Queen Bedsbr★ 1 Queen sofa bed in the basement br★ Free parking on the drivewaybrbr★ LOCATION:brYou’ll be just 3 minutes from downtown Shelbyville, with easy access to local restaurants, shops, and essentials. Perfectly situated for exploring the Kentucky Bourbon Trail, this home makes an ideal home base for distillery tours, weekend escapes, and special celebrations.brbr★ THE EXPERIENCE:brStart your mornings slow with coffee on the porch, spend your afternoons exploring bourbon country, and end your nights soaking in the hot tub or sharing stories around the fire. Whether you're here to celebrate, relax, or explore, this home delivers a stay that feels both elevated and effortless.brbr★ PETS: You may bring two dogs. Each dog costs $75 each***brbr★ LOCATION INFORMATION ★br• 0.7 (3 minutes) to Shelby County Fairgroundsbr• 0.9 mile (3 minutes) to downtown historic Shelbyville br• 1.1 mile (4 minutes) to The Lot, Food Truck Parkbr• 1.8 miles (7 minutes) to Krogerbr• 2.7 miles (9 minutes) to Walmartbr• 4.7 miles (11 minutes) to Jeptha Creed Distillerybr• 5.2 miles (12 minutes) to Bulleit Distilling Companybr• 8.3 miles (16 minutes) to The Outlet Shoppes of the Bluegrassbr• 9.5 miles (16 minutes) to Mulberry Orchardbr• 23.6 miles (34 minutes) to Buffalo Trace Distillery br• 26.8 (38 minutes) to Wild Turkey Distillerybr• 29.4 miles (39 minutes) to Four Roses Distillery br• 32.2 miles (36 minutes) to Woodford Reserve Distillerybr• 31.0 miles (35 minutes) to Louisville International Airportbr• 30.0 miles (35 minutes) to Kentucky Expo Centerbr• 32.2 miles (38 minutes) to Louisville Downtownbr• 33.4 miles (40 minutes) to Churchill DownsbrbrOTHER THINGS TO NOTE: br★ SECURITY PURPOSES ★brThere are home exterior cameras on the property, one on top of the garage facing the driveway and a Ring doorbell on the front door. All of these cameras record audio and visual. There are no cameras inside.brbr★ NATURE★ brThis is Kentucky, there are insects, bugs, snakes and other critters in the area. We do have a regular service of pest control, but if you do see insects and bugs in the house, this is the nature of being in the south. When outside, please be mindful of snakes and critters.brbr★ TRAVEL INSURANCE ★brPlease obtain travel insurance for your trip as I do not offer refunds for any reason. Unfortunately, things can happen that are out of your control, such as flight cancellations, illnesses or unforeseen circumstances. You will be happy you have coverage if something unexpected interrupts your trip. brbr★ FIREWOOD ★brMake sure to stop at Kroger, Walmart or another local place to pick up some firewood before heading to the home.brbr★ CANCELLATIONS ★brPlease note, VRBO cancellations are eligible for a refund of 97%, issued to the original form of payment.brbrMagnolia Bourbon Manor is in a beautiful, quiet neighborhood. Please be mindful of our neighbors and keep the noise to a minimum.brbr• The house is professionally cleaned and disinfected in between every guest stay.br• Minimum rental age 25brbrIn order to gain access to the directions and door code, please acknowledge the below. The address and door code WILL NOT be given out until these are accepted. br- NO parties or large eventsbr- NO smoking in the house (cigarettes, cigar, weed, vape, candles, etc)br- NO loud noise after 10pmbr- Rental agreement is signedbrbrGuests will have access to the whole house, the backyard and front yard.brbrGuests can reach me through the app

Bed

Bath

Sleeps

$361.92

/ Nightly

Private Vacation Home

Bourbon Trail*Hot Tub*Sauna*Mini Golf*WiFi*EVSE

Shelbyville, Kentucky, United States

Welcome to The BarrelWoods, a modern-rustic retreat in the heart of the Bourbon Trail. Enjoy the firepit, hot tub, or barrel sauna, and have fun with mini golf, archery, disc golf, or the game room with air hockey and shuffleboard. Near iconic distilleries, dining, and scenic parks, it’s the ultimate getaway base.brbr THE SPACEbrThis newly built, one-level home sits on 1 acre in Shelbyville, KY. Designed with comfort and entertainment in mind, it offers 3 bedrooms, 2 bathrooms, and space for up to 8 guests.brbr ️INDOOR LIVING brStep into The BarrelWoods, where vaulted ceilings and an open layout create a bright, welcoming space. Relax in the living area or around the eight-seat dining table. The gourmet kitchen features stainless steel appliances, a stocked coffee bar (drip and K-cup), and all cookware and essentials, including a toaster, mixer, and crockpot.brbr ️Sleeping arrangements:brPrimary: King bed, TV. Sleeps 2brBedroom 2: King bed, TV. Sleeps 2brBedroom 3: King bed, TV. Sleeps 2brLiving room: Queen sleeper sofa. Sleeps 2brbr The game room offers air hockey, shuffleboard, foosball, an arcade machine, Xbox, and board games for fun at any age.brbr OUTDOOR LIVINGbrStep into a serene outdoor oasis with a hot tub under the stars, a barrel sauna, and plenty of space for fun and relaxation. Enjoy archery, mini golf, disc golf, or gather around the fire pit for s’mores. Relax on the front and back porches with coffee or wine and fire up the Weber grill for BBQ meals.brbr ️CONVENIENT AMENITIESbrEV chargerbrStarlink internet (speed may vary)brNetflix streamingbrWasher and dryer. brWeber Grill.brLinens and towels are provided. brbrA starter supplies kit is provided, including toiletries and kitchen essentials.brbr✔️The home is child-friendly but not childproof. br✔️Please remove shoes indoors.brbr PET POLICY brWe allow one dog per booking with prior approval and a $200 non-refundable pet fee. Pets must be added to the reservation at booking.brbrIMPORTANT: Our neighbors have dogs that may occasionally bark, especially at movement or wildlife. White noise machines and earplugs are provided for guests sensitive to noise.brbrGUEST ACCESSbrGuests have access to the entire home except two linen closets and cabinets in the laundry room.brbr EXPLORE THE WONDERS AROUND YOUbrExplore Shelbyville, KY, a charming hub of bourbon, history, and outdoor fun. Tour Bourbon Trail distilleries, stroll historic downtown, or enjoy hiking, biking, and picnics at Clear Creek Park and Lake Shelby. brbr Distilleries (drive distances)br15 minutes Jeptha Creed Distillerybr19 minutes Bulleit Distilling Co.br20 minutes Whiskey Thief Distilling Cobr31 minutes Castle & Key Distillery brbr Breweriesbr15 minutes Talon Winerybr27 minutes Rising Sons Home Farm Winerybr32 minutes Lovers Leap Vineyards and Winerybrbr⭐️ Places to Visitbr14 minutes Guist Creek Lake br16 minutes Wakefield-Scearce Gallerybr16 minutes Shelby County Community Theatrebr18 minutes Clear Creek Park br24 minutes Kismet Horse FarmbrbrRENTAL AGREEMENTbrbrPLEASE READ THIS AGREEMENT IN FULLbrBy completing this reservation, you confirm that you have read and agreed to all terms, rules, and policies. The initial payment serves as your electronic signature. The Host/Owner leases the Rental Property to Guest(s) under the following terms and conditions.brbrRULES AND REGULATIONSbrGuests must follow all rules in this agreement, the property book, and posted signage. Keep the premises clean and safe; no unsafe / unsanitary conditions. No commercial use, illegal substances, firearms, or hazardous items. All-terrain vehicles and motorcycles are prohibited. Violations may result in immediate eviction without refund.brbrOCCUPANCYbrMax 8 guests including children. No subletting. Violations may result in immediate eviction without refund. Guests authorize Owners to enter for inspections if damage, excess guests, or unauthorized pets are suspected, or for maintenance/repairs.brbrAGE 25 OR OLDER TO BOOKbrBooking guests must be 25+ years old and may provide government ID. Booking guests must stay at the place and cannot book for others without staying.brbrNO PARTIES OR EVENTS, NO OUTSIDE VISITORS, NO OVERNIGHT GUESTSbrbrNO ILLEGAL SUBSTANCES AND ACTIVITIESbrIllegal substances/activities are prohibited and may result in immediate eviction. Guests are responsible for any and all costs incurred by the Host; no refund will be provided.brbrPROPERTY CONDITIONbrNo refunds will be provided for inoperable appliances, hot tub, sauna, TV, games, power outages, or natural events. Owners will restore amenities promptly with no rental concessions. No refunds will be given due to power blackouts, water shortage, flooding, snow, construction at adjacent properties, or mandatory evacuations of the area by government officials due to potentially dangerous situations arising from acts of God or nature. Travel insurance is recommended.brbrGENERAL PROPERTY RULESbrNo food/drink in bedrooms; guests will compensate the host for any food/drink stains in the bedrooms.brFurniture must remain in place; moving may cause damage.brTowels are provided. Bed linens are provided and must be used on all beds. Guests pay for lost/damaged items.brQuiet hours 10 PM–7 AM; violations may incur fines or eviction.brNo smoking/vaping/hookah ($200/day penalty).brNo fireworks: violations may result in eviction/fines.brCheck-out on time; guests are responsible for losses from rule violations.brbrAIR CONDITIONING / HEATINGbrThe house has central A/C and heating, extra heaters, and a portable fan. The game room has its own mini-split system for heating and cooling.brbrPET POLICYbrOne dog per booking is allowed with prior approval and a $200 non-refundable pet fee, paid at booking. Dog must be at least 1 year old and fully potty trained. Guests are responsible for damage and cleaning. No dogs are allowed on furniture, counters, hot tub or sauna; and never should be left alone. Dogs must use the bathroom outdoors and the guest must clean up and use the driveway bins for disposing of waste. Dogs must be leashed and supervised outside. Pets must be well groomed for the comfort of future guests and staff. Hosts are not responsible for interactions with other pets, wildlife, or insects.brbrWIFIbrStarlink internet; speed may vary due to weather/satellite conditions.brbrTRASH POLICYbrAll trash/recycling must be in 13+ gallon bags and placed into the trash bins located outside at the beginning of the driveway in a wooden enclosure. No small, grocery, or pet bags; no trash left outside.brbrADDITIONAL CLEANING IS AN EXTRA CHARGEbrExtra cleaning beyond standard service may incur a fee, determined by the host based on the property condition.brbrGUEST AGREES TO PAY FOR DAMAGES EXCEEDING DEPOSITbrGuests must pay for any damage exceeding the deposit. Damage will be billed and reported to the rental platform.brbrLOST AND FOUNDbrLost & Found items: $30 + shipping fee. Items unclaimed after 7 days will be disposed of.brbrINABILITY TO TRAVELbrNo refunds for inability to travel due to circumstances beyond Owner control (weather, disasters, change of plans). Travel insurance is recommended.brbrCANCELLATION POLICYbrFull refund 30 days or more before check-in. 50% refund 14-30 days before check-in; none after.brbr*All refunds are subject to a 4% deduction to cover credit card processing fees.br*Canceled reservations forfeit any retained payment, which cannot be credited, transferred, or reused. Cancellations are final; new bookings must follow current terms and rates.brbrRescheduling: Not allowed ≤30 days before check-in; 30 days subject to availability with a rate difference applicable, and one change per reservation allowed. Travel insurance is recommended.brbrHOT TUBbrThe hot tub is checked prior to each stay; it can be cold on arrival if it is refilled on the guest check-in date. Guests must follow posted rules. No foreign substances allowed (alcohol, soap, oils, food, glass), $200 cleaning fee if any substance is found. Children must be supervised. Cover damage: $700. Horseplay is prohibited. Use it at your own risk; hosts are not liable for injury, accident, or death.brbrSAUNA & WAIVER OF LIABILITYbrGuests assume all risks using the sauna. Max 4 people. No smoking, food, pets, or rough handling. Guests must follow the rules and pay for any damages. If any additional cleaning is needed, guests must pay a fee of up to $400.brbrFIRE PITbrKeep the area clear. Always supervise. Follow local fire laws; fully extinguish fires after use.brbrFIREWOODbrFirewood is provided; use it responsibly. Do not collect wood from the property and burn only firewood/kindling.brbrSECURITY CAMERASbrTwo exterior cameras are always active and recording: one at the front of the house monitoring the walkway, front door, and porch, and one on the side overseeing the driveway. A Ring doorbell is also always recording. Tampering may result in cancellation of the stay. No cameras are inside, in the backyard, or near the hot tub/sauna/fire pit.brbrPRIVATE SEPTICbrThe property has a private septic system. DO NOT FLUSH anything other than toilet paper (septic safe toilet paper is provided). Guests are responsible for repair costs if improper products are flushed and clog the septic system.brbrINDEMNITYbrIf the property is unavailable, the owner’s sole liability because of this unavailability is to provide a full refund. Guests must indemnify owners against injury or damage on the property.brbrBREACH OF TERMS: Violation of terms may result in immediate eviction without refund. Guests acknowledge risks of outdoor, water, and natural activities, assume responsibility for themselves and minors, must follow all laws, return the property in original condition, and indemnify owners against loss, damage, or injury. This agreement is governed by Kentucky law, is the entire Agreement, may only be amended in writing, and disputes may only be filed in the County where the property is located. If any part is unenforceable, the remainder stays valid.brbrFull terms & conditions will be provided after the reservation is confirmed.brPLEASE READ

Bed

Bath

Sleeps

$2136.15

/ Nightly

Private Vacation Home

Flint Ridge Reserve - Sleeps 29 - Heated Pool/HotTub - Golf Sim - Arcade - Games

Shelbyville, Kentucky, United States

Welcome to a one-of-a-kind luxury retreat designed for unforgettable group stays, celebrations, and family getaways. Thoughtfully crafted for up to 29 guests, this 10-bedroom estate blends elevated design with nonstop entertainment—creating an experience you won’t find anywhere else.brbrStep outside to your private resort-style pool, hot tub, and sauna, perfect for sunny afternoons, evening cocktails, or late-night relaxation under the stars.brbrThe spacebrSpacious bedrooms, plush linens, and high-end furnishings create a restful and refined atmosphere. All bedrooms include ceiling fans, room darkening shades, and smart charging stations to ensure a peaceful night of sleep.brbrBedding accommodationsbr28 total plus pack n play for infantbr-7 king bedsbr-4 queen bedsbr-2 queen sleeper sofasbr-1 daybed with trundle for 2 kids/small adults located in primary bedroombrbr Upstairs - 10br1-king bed, en suite bathroom, 50” smart TVbr2-queen bed x 2, access to Jack n Jill bath, 50” smart TVbr3-king bed, access to Jack n Jill bath, 50” smart TVbr4-king bed, 50” smart TVbrbr Main - 6 + pack n playbr1 - King bed, en suite bathroom, office desk, massaging glider, and 65” smart TVbr-Day bed + trundle (2 twins for kids)br-Queen sleep sofa (poly and bark) located in living roombr+ pack n play in primarybrbr Downstairs - 12br1-king bed, 50” smart TVbr2-king bed, 50” smart TVbr3-king bed 40” smart TVbr4-queen bed, 40” smart TVbr5-Queen bedbrQueen sleeper sofa (poly and bark) in bonus room with 65” smart TV, bourbon bar, and refrigerator.br⸻br Movie Theater & Karaoke Lounge brStep into your own cinematic experience featuring a 100” TV equipped with 8 leather reclining theater chairs and blanketsbrbrIn the corner, you’ll find a karaoke lounge complete with:br• Professional karaoke system with lyric display screen and LED entertainmentbrbrPerfect for movie nights, big games, or singing the night away with family and friends.br⸻br Ultimate Golf & Game Garage include:br• SkyTrak Golf Simulator - play on the range or your favorite iconic course!br• 100 TV br• Pool tablebr• Shuffleboardbr• Ping Pongbr• Dart boardbr• Poker tablebrbrArcade Classics Throughout Flint Ridge Reserve:br• Terminatorbr• Fast & the Furiousbr• Mortal Kombatbr• Pac-Manbr• Golden Teebr• NBA Jambr• Air Hockey Tablebr⸻brPool is seasonal from April to OctoberbrPool is offered heated at additional $75/night during the months of April to Memorial Day and September til end of season in October. Must left me know 48 hours before booking.brPool is winterize and not available December through February.brbrBackyard also includes:br- 3 Hole Disc Golf Coursebr- Outdoor Fireplacebr- Weber Gas Grillbr- Saunabr- Hot Tubbr- Covered outdoor diningbrbrDog Friendly Guests Welcomebr2 Large dog cratesbrFood and water bowlbrFenced in backyard with poop bagsbrDogs are not allowed on furniturebrGray dog towels to be used for muddy pawsbrUp to 2 dogs under 60 lbsbr⸻br Bourbon Trail Access to the best of Kentucky’s distilleries just minutes away from:brFour Roses DistillerybrWild Turkey DistillerybrBardstown Bourbon CompanybrWoodford ReservebrWillett DistillerybrHeaven Hill DistillerybrOld ForesterbrBuffalo TracebrLux RowbrJeptha CreekbrbrDesigned for Memory-Making:brWhether you're unwinding in the hot tub, sharing stories by the fire, or enjoying a night of bourbon tastings, every inch of this home is built for unforgettable moments. A perfect blend of Kentucky character and modern luxury.brbrHouse rules:brNo parties.brGeneral Quiet Hours 10pm-7am. In accordance with local regulations and respect for our neighbors, please be mindful of excessive, unnecessary, and unreasonable noises.brNo smoking. Professional cleaning of interior spaces or garages will be $750.brNo glass on pool deck.brUp to 2 dogs allowed with $200 additional fee. Bringing a pet without authorization will result in penalty.brMax occupancy of 29 guests, should the reservation exceed the maximum, reservation is subject to cancellationbrNo parking on street, park in driveway onlybrThere is one external camera on the property for guest safety.brbrGuest accessbrThe entire house, pool, and property is yours.

Bed

Bath

Sleeps

$352.45

/ Nightly

Private Vacation Home

Heritage House 1900’s home part/close to the Bourbon Trail

Shelbyville, Kentucky, United States

HeritageHouse is 19th century home locate as part of the Bourbon Trail in Shelbyville Kentucky. This house is lovely restored! It have a full kitchen and separate dining area . Great community and located 38 minutes from Churchill Downs!

Bed

Bath

Sleeps

$161.48

/ Nightly

Apartment

Unique Downtown Studio with an Industrial Vibe

Shelbyville, Kentucky, United States

The Underground is a stylish and completely remodeled studio with a full bath that boasts an industrial vibe and is conveniently located on the lower-level of the Stables Workspace. With zero steps and attractive lighting, this rental is easily accessible and welcoming.brbrInside, guests will find a cozy and comfortable Queen Murphy Bed, as well as a bar with a concrete countertop and a small convection oven/microwave combo, perfect for preparing quick meals or snacks. A mini refrigerator is also included, providing a convenient way to store drinks and keep them chilled.brbrThe tiled shower adds a touch of luxury to the bathroom, while the swanky furniture throughout the space adds to its overall chic and modern appeal.brbrBut the convenience of The Underground doesn't end there. Centrally located in downtown Shelbyville, guests will have easy access to all the amenities and attractions this charming town has to offer. Whether you're in town for business or pleasure, The Underground provides the perfect home base for your stay.

Bed

Bath

Sleeps

$552.88

/ Nightly

Private Vacation Home

Hot Tub | Firepit | Putting Green | 5 Bedrooms

Shelbyville, Kentucky, United States

Summary:brbrRetreat to this beautifully updated 5-bed, 3-bath home in a quiet neighborhood between world-famous bourbon distilleries. With a hot tub, fire pit, pergola lounge, putting green, and spacious interior, it’s perfect for groups seeking comfort, style, and proximity to Kentucky’s iconic Bourbon Trail.brbrbrbrThe Space:brbrKey Features:brbrbrbr☀ Sleeps 10 comfortablybrbr☀ 5 bedrooms with king bedsbrbr☀ 3 full hallway-accessible bathroomsbrbr☀ Hot tub + pergola lounge areabrbr☀ Fire pit + outdoor seatingbrbr☀ Golf putting greenbrbr☀ Fully stocked gourmet kitchenbrbr☀ Dining for 12brbr☀ Pet friendly + kid friendly (no toys or gates)brbr☀ High-speed internetbrbr☀ Quiet neighborhood near major bourbon distilleriesbrbr☀ Off-street parking for 4 on the pad + 1 in front of the home (no street parking near neighbors)brbrbrbrbrbr✨ BEDROOMS ✨brbrbrbrEvery bedroom was designed with relaxation in mind, offering king beds, soft lighting, and peaceful décor—perfect for unwinding after long Bourbon Trail adventures.brbrbrbrFirst Floorbrbr• Bedroom 1: King bed with cozy textures and easy access to the main living areas; uses the first-floor hallway bathroom.brbr• Bedroom 2: King bed tucked quietly toward the rear of the home; uses the first-floor hallway bathroom.brbr• Bedroom 3: King bed wrapped in warm tones and natural light; uses the first-floor hallway bathroom.brbrbrbrSecond Floorbrbr• Bedroom 4: King bed with elevated views and privacy; uses an upstairs hallway full bathroom.brbr• Bedroom 5: King bed offering comfort and calm; uses the upstairs hallway full bathroom.brbrbrbr✨ BATHROOMS ✨brbrbrbrYour group will enjoy three full bathrooms, each conveniently located off hallways for shared access. All bathrooms are fully stocked with body wash, shampoo, conditioner, plush towels, and essential toiletries, making travel easy and stress-free.brbrbrbr✨ KITCHEN & RELAXING AREAS ✨brbrbrbrThe fully stocked kitchen is designed for cooking, celebrating, and gathering. With modern appliances, cookware, dishware, and both everyday and gourmet essentials, meal prep becomes part of the experience. The elegant dining room seats 12 guests, ideal for dinner parties or bourbon tastings.brbrbrbrRelax in the warm, inviting living area with comfortable seating and beautiful wood-beam accents—perfect for game nights, morning coffee, or unwinding after distillery tours.brbrbrbr✨ OUTSIDE SPACE ✨brbrbrbrThe backyard is your private oasis. Enjoy the hot tub under the pergola, complete with lounge seating for unwinding in any season. Gather around the fire pit for s’mores and conversation, or challenge your friends on the golf putting green. With mature trees, curated seating, and plenty of space, the outdoor area was designed for memory-making.brbrbrbrOff-street parking includes four spaces on the rear parking pad via the alley and one space in front of the home. No street parking is permitted near neighbors.brbrbrbr✨ Book Today & Let Us Take Care Of You ✨brbrbrbrWhether you’re exploring the Bourbon Trail, hosting a getaway with friends, or gathering family for a peaceful retreat, this home blends comfort, style, and convenience. Reserve your stay with Sixgen Rentals and let us handle the rest.brbrbrbrbrbr** NOTE: Rental Property Agreement is required to be signed up after reservation has been confirmed. Failure to comply will result to the cancellation of reservation without refund.brbrbrbrGuest Access:brbrGuests will receive a 4-digit code to access the smart lock on the front door for a seamless and secure check-in experience.brbrbrbrOther Things to Note:brbrThis property is equipped with two outdoor security cameras, one facing the front door and one overlooking the backyard, to help ensure guest safety and protect the home. We also use a Minut noise-monitoring system, which detects noise levels and smoking both inside and outside the property. This system does not record audio; it simply alerts us if noise or smoke levels exceed acceptable limits. These measures are in place to help maintain a safe environment and ensure guests adhere to our rules regarding noise, smoking, and occupancy.brbrbrbrAfter confirming your reservation, you’ll receive access to our Guest Portal, which must be completed before check-in. It includes your check-in instructions, house rules, and required guest information.brbrbrbrYou will also be asked to review and sign our external rental agreement. During this process, you’ll have the option to purchase a nightly damage protection plan (damage waiver) for coverage against accidental damages during your stay.brbrbrbr Pet-Friendly StaybrbrWe’re happy to welcome pets in our property! We allow up to 2 pets, and there is a $100 pet fee per pet. Please inquire and let us know in advance if you’re bringing pets so we can add the fee to your reservation. This helps us prepare the space and ensure a comfortable stay for you and your furry friends.

5

Bed

3

Bath

12

Sleeps

$238.18

/ Nightly

Private Vacation Home

Parris on Main - Perfect for downtown Shelbyville, Bourbon Trail, and the Derby

Shelbyville, Kentucky, United States

About this spacebrParris on Main Street is the perfect location to enjoy the historic town of Shelbyville and, a few blocks walking distance to many antique shops, local coffee houses and great locations to grab a bite to eat.brbrNewly 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 DownsbrbrThe space - brThis house features 3 bedrooms, 2.5 bathrooms plus an additional sleep room off the sun-room in the second bedroom.brbrThe master bedroom is a dream! Complete with it's own private sun-room with seating and coffee maker in the back, plus a private bathroom with a brand new large walk-in shower.brbrbrGuest accessbrFront door has keypad - guests will be sent code before arrival.brbrThe house is located right there in the heart of downtown on Main Street, with a private driveway and parking in the back of the house.brbrOther things to note - brWhile we have preserved the originality of the home including gorgeous hardwood throughout. We have added new modifications and modern appliances for a more comfortable stay.brbrAlso the house has an air mattress with sheets, as well as a pack n play.brbrbrbrPlease enjoy your stay. You have full access to the home and all the amenities! We appreciate privacy and want to make sure you have the same. However, we are a phone call away if there are any issues. brbrHulu is setup on the TV - Parris on Main Guest; please enjoybrbrAny food/drink in the house is fair game - help yourself. brbrCheck out - we do not require any special cleaning as you pay for that luxury. If you would like to start the dishwasher or laundry on the way out, that would be great, but 100% optional. br

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Bath

Sleeps

$467.46

/ Nightly

Private Vacation Home

Beautiful, Peaceful Lakefront home in ❤️ of Bourbon Country in Shelbyville, KY

Shelbyville, Kentucky, United States

Peaceful, Beautiful 4 bedroom, 2 bathroom house sitting on Guist Creek Lake in Shelbyville, KY located very close to the Bulleit Bourbon Distillery. Lake view from two of the four bedrooms. Perfect for bird watching. Guist Creek Lake is a great kayaking and fishing lake. Patio off the main living room with patio table and chairs. Two comfortable living room spaces with smart TVs, games, and books. Beautiful sunroom overlooking the lake. Nice patio space. Lake access with boat dock.

4

Bed

2

Bath

7

Sleeps

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