Vacation Home Rentals By Owner In Frankfort, KY

Your Frankfort adventure begins at this 3-bedroom house. Each bedroom features a comfortable king bed, perfect for a restful night. The home offers two bathrooms, including both a shower and a bathtub, making it easy for guests to refresh after a day of exploring the Bourbon Trail. Enjoy a charming and tranquil atmosphere throughout the space, where you can relax and unwind. Whether you’re gathering with friends or enjoying some quiet time, this delightful house provides a welcoming retreat. We think our place will help you experience everything Central Kentucky has to offer. Spend the day sampling Kentucky's finest bourbon, touring the local horse farms or watching the races at Keeneland for the spring and fall meet.

3 King Beds - Bourbon Trail - 2 Miles to Buffalo Trace - Farm Tours

Frankfort, Kentucky, United States

Bed

2

Bath

6

Sleeps

$239.98

Escape to 'Valor Circle Cottage,' your pet-friendly Frankfort retreat in the heart of Bourbon Country! This updated 2-bed, 2-bath home comfortably sleeps 4. Features include a dedicated workspace with fiber internet, a fully fenced backyard with a firepit, and a prime location just 2 miles from Buffalo Trace Distillery. Perfect for bourbon tours, work-from-home stays, or a relaxing getaway.brbrStep inside and feel the warm, inviting atmosphere where old-world charm meets modern comfort. Natural light streams through the windows, illuminating tasteful, bourbon-themed decor and creating a bright, welcoming environment.brbr Living Area: Relax in the updated living room, featuring a large flat-screen TV. A dedicated workspace with high-speed fiber internet is also available for your convenience.br Bedrooms & Bathrooms: Unwind in two comfortable bedrooms. The upstairs master features a king-sized bed and TV, while the downstairs bedroom offers a queen-sized bed and TV. The home includes a full upstairs bathroom with a shower/bath combination and a fully remodeled downstairs bathroom with a walk-in shower.br Kitchen & Dining: Your fully equipped kitchen includes a coffee maker, Keurig, blender, Crockpot, and toaster. Gather for meals at the adjacent dining table.br Outdoor Living: Enjoy your private, fully fenced-in backyard. The space includes a porch with patio seating, a BBQ grill for cookouts, and a firepit with seating for four to enjoy a nice evening under the stars.brbrGuests will have private and exclusive access to the entire home, including the front porch and the fully fenced backyard. The only exception is a locked basement area which is used for owner storage and is not accessible to guests.brbrWe respect our guests' privacy and offer a self-check-in process. We will not be on the property during your stay but are always available via the booking app or phone if you need anything or would like local recommendations.brbrSecurity: For your peace of mind, the property exterior is monitored by security cameras. There are no cameras inside the home.brPet-Friendly Yard: The backyard is fully fenced, providing a secure and private space for your furry friends to enjoy.brbrOur cottage is decorated for Christmas!

2bd 2bath, Bourbon Trail Cottage Fenced Yard

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$552.92

Enjoy our 2 story home, 5 bedrooms plus one room with a futon also, decor that features Kentucky Bourbon and Horse Racing. Our home is situated on 2.5 acres and backs up to Benson Creek. The home consist of 3 levels. We have a fenced in area that is ideal for pets or small children. Ideally located for Bourbon Tours, Vineyards, Breweries, trips to Keeneland or Churchill Downs, UK/UL/KSU or visits to the Capital.brbrThe top level has 3 bedrooms (1st BR has 2 twin beds, 2nd BR has 1 Queen bed and 3rd BR has a full size bed and a futon) and 1 bath, the main level host living room, dining room, kitchen and eat in area along with washer and dryer and half bath, the lower level has 2 more bedrooms (4th BR has 1 queen bed and 5th BR has 1 full bed) a living room with a queen size pull out sofa sleeper and a full bath.

H-DERBY, Keeneland, Bourbon or Family Gathering!

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$431.57

Only 5 minutes from the interstate and nestled atop a tranquil hill, this home offers unparalleled serenity with breathtaking views of sprawling farms. Spanning 70 acres, it's a haven where wildlife thrives, adding to the peaceful ambiance while also minutes away from all that Frankfort has to offer. With 4 bedrooms and 3.5 baths, it's ideal for families seeking ample space and comfort. This home is 5 minutes from the interstate and minutes from several stops on Kentucky's famous Bourbon Trail!

Home in Frankfort countryside-close to distilleries, Keeneland &Churchill Downs!

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$943.03

★ Escape to The Bourbon Barrel Retreat ★brbrYour perfect group getaway awaits at The Bourbon Barrel Retreat — a modern 6BR home designed for comfort, fun, and unforgettable memories. Gather around the fire pit, unwind in the hot tub, challenge friends in the game room, or enjoy cozy movie nights in the private home theater. All this, just minutes from Kentucky’s world-famous bourbon distilleries.brbrBOOK YOUR STAY TODAY! brbr★ Modern 6BR Retreat w/ Hot Tub, Game Room & Theater ★brThe spacebrWelcome to The Bourbon Barrel Retreat, a spacious home crafted for group stays in the heart of Bourbon Country. With BRAND NEW stylish interiors, generous living spaces, and all the amenities for fun and relaxation, it’s the ideal destination for families, friends, or bourbon-themed getaways.brbrWhether you’re exploring nearby distilleries, sharing laughs over a game of pool, or watching the big game in the theater room, this retreat offers a perfect blend of luxury, entertainment, and Kentucky charm.brbr★ Highlights & Amenities ★brbr- 6 Bedrooms • 3.5 Bathrooms • Sleeps 16br- Private 7+ acre estate with rolling hills viewbr- All BRAND NEW Beds & Linens, Furniture and Decorbr- Covered Hot Tub & Outdoor Fire Pitbr- Backyard Putting Green to improve your gamebr- Outdoor Games: Cornhole & Giant Jengabr- Large Game Room w/ Pool Table, Darts, Bar and Games for the whole familybr- Home Theatre equipped with stadium like popcorn machine and a Big-Screen Projectorbr- Fully Equipped Chef’s Kitchen w/ Stainless Steel Appliances + Dining Areabr- Cuisinart Coffee Center 2-in-1 Coffeemaker, 12-Cup Glass Carafe, Automatic Hot & Iced Coffee Maker, Single Server Keurigbr- Spacious Upper Deck & Lower Patio w/ Outdoor Seating and Dining Options and Propane Grillbr- High-Speed Wi-Fi + Smart TVs in every bedroombr- Desk Area for work while awaybr- Full Access to Washer/Dryer in laundry roombr- Self Check-In Smart Lock + Professional Cleaningbr*Friendly horses live next door and are often near the fence—kids and adults love saying hello!*brbr★ Bedrooms & Bathrooms★brbr- Bedroom 1: King bed, walk-in closet, Smart TV + en-suite bath with soaking tub and rain showerbr- Bedroom 2: King bed, walk in closet, Smart TV + jack&jill Bathroom with rain showerbr- Bedroom 3: King bed, walk in closet, Smart TV+ jack&jill Bathroombr- Bedroom 4: Queen bed, walk in closet, Smart TVbr- Bedroom 5: 2 Queen beds, walk in closet, Smart TV + jack&jill Bathroom with rain showerbr- Bedroom 6: 2 Queen beds, walk in closet, Smart TV + jack&jill BathroombrbrEach room features plush bedding, smart TVs, and stylish touches to ensure comfort and enjoyment for every guest.brbr★ Perfect for Every Occasion ★brbr✔ Bourbon Trail adventuresbr✔ Family reunionsbr✔ Weekend getaways with friendsbr✔ Game days & movie nightsbr✔ Getaways in the Bluegrass hill country with beautiful rolling hills views to relax, unwind and rechargebrbrbrReady to relax, reconnect, and make memories BOOK YOUR STAY TODAY! brbr★Distilleries & Bourbon Experiences Close by★br- Whiskey Thief Distilling Co. (~4 miles) — a small-batch bourbon distillery on a working farm.br- Wild Turkey Distillery (~13 miles)br- Buffalo Trace (~14 miles)br- Four Roses Distillery (~14 miles)br- J. Mattingly 1845 Distillery (~14 miles)br- Castle & Key Distillery (~17 miles)br- Glenn’s Creek Distillery (~17 miles)br- Jeptha Creed Distillery (~20 miles)br- Bluegrass Distillers (~21 miles)br- Barrel House Distilling Co (~33 miles)br- Kentucky Artisan Distillery (~42 miles) — a craft distillery with farm-to-bottle process.brbr★ → Top picks Nearbybrbr★Wineries & Breweries★brbrLovers Leap Vineyards & Winery (Lawrenceburg) — scenic Kentucky vineyard.brbrProdigy Vineyards & Winery (Frankfort) — casual atmosphere, local wines.brbrWest Sixth Farm Brewery (Frankfort) — local craft beer in a beautiful farm setting.brbr★Horse & Kentucky Heritage★brbrThe Kentucky Castle (Versailles) — a real castle with tours, dining, and spa.brbrKeeneland Racecourse (Lexington) — iconic horse racing & tours.brbrKentucky Horse Park (Lexington) — horse museum, shows, and farm tours.brbr★Outdoors & Adventure★brbrElkhorn Creek — popular for kayaking, canoeing, and fishing.brbrSalato Wildlife Education Center (Frankfort) — family-friendly spot with trails & animals.brbrVertigo Bungee (Lawrenceburg) — thrill-seekers can jump from a bridge over the Kentucky River.brbr★History & Culture★brbrKentucky State Capitol & Gardens (Frankfort) — beautiful grounds and free tours.brbrOld State Capitol & Kentucky Historical Society — dive into Kentucky’s history.brbrDowntown Frankfort — charming small-town shops, local dining, and river views.brbr★ Peace of Mind & Guest Comfort ★brbr✔ Professionally cleaned & sanitizedbr✔ Contactless self check-in via Smart Lockbr✔ 24/7 guest support messaging in app and direct phone numberbr✔ Security cameras on the exterior of the home only. This is to ensure security and safety for our guests and homeownersbr✔ Stocked essentials like shampoo, conditioner, and body wash. Fully loaded kitchen and popcorn for the stadium like popcorn machine. Hot Tub Towels, etc.brbr★ HOUSE RULES ★brbrMust be 21+ to book.brMAX Occupancy: 16 guests. No unregistered guests allowed. We do not allow parties.brPlenty of parking available on the 7+ acre estatebrNo smoking inside the property — $750 ozone cleaning fee if violated. Smoking outside is allowed if cleaned up.brNo parties or events. Violations will result in $600 fee + cancellation.brNo pets unless pre-approved brNo shoes in the housebrExterior security cameras are in place for safety.brbr★ HOT TUB RULES ★brbrNo glass near the hot tub.brNo food, diving, or jumping.brShower before entering.brChildren must be supervised at all times.brUse at your own risk.brKeep cover on when not in use.brDo not adjust settings above 104°F.brNo tampering with controls or adding substances.brLimit time in hot tub for safety.brReport issues immediately to the host.brGuest accessbrGuests have full access to the entire home and all outdoor amenities, including the hot tub, putting green, fire pit, hot tub and upper deck area. You'll be provided with a unique code for our electronic lock - no key pickup required. Check-in is contactless and seamless for a smooth stay!brOther things to notebrMax Occupancy: 16 guestsbrbrbrWe provide all linens, hot tub towels, and personal care essentials (shampoo, conditioner and body wash)brbrThe roads and driveway leading to the home are easily accessible and easy to navigate with Apple or Google MapsbrbrLocated in the heart of Kentucky’s Bourbon Trail, our home is just minutes from the world-famous Buffalo Trace Distillery, along with Woodford Reserve, Four Roses, and more. Downtown Frankfort offers charming restaurants, breweries, and local shops, giving you the perfect mix of bourbon, bites, and small-town charm.brbrBOOK YOUR STAY TODAY!

Bourbon Trail Estate - Theater, Games & Hot Tub

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$511.46

In the heart of the Kentucky Bourbon Trail, Enjoy the Bourbon Hills Retreat located approximately 7 miles from downtown Frankfort in the peaceful hills of Kentucky. The property sits on 13 acres and was completely renovated in 2023. Enjoy your morning coffee on the front porch rocking chairs or wind down in the evening enjoy a nice glass of wine and watch shooting stars from the hot tub. Centrally located equal distance between Louisville & Lexington. Frankfort and surrounding areas have so much to explore. brbrDistilleries Nearby:br★ Buffalo Trace- 10 miles ★ Castle and Key - 15 milesbr★Bulleit Distillery- 10 miles ★ Woodford Reserve- 22 milesbr★ Whiskey Thief- 10 miles ★ Wild Turkey- 22 milesbr★ Glenns Creek - 11 miles ★ Four Roses- 25 milesbrbrLIVING:br-Beautiful, spacious area with comfortable seating for the entire groupbr-65in Roku TV for your favorite sporting eventsbr-The perfect spot to relax with friends or family after a day of bourbon tasting.brbrDINING/KITCHEN:br-Fully stocked kitchen area for all of your cooking and baking needsbr-Beautiful buffet bar stocked with glassware for your at-home tastingsbr- Bourbon ball ice cubes waiting in the freezerbr-Stocked coffee bar with drip and Keurig option. (K-Cups, Coffee grounds, creamer, and sweeteners provided.)br-Spacious countertops to make cooking easybr-Island perfect for your charcuterie board spread brbr1st floor PRIMARY BEDROOM:br-Spacious, luxurious bedroom with a comfortable Novaform King mattressbr-Welcome to your Kentucky getaway retreat space with a private bathroombr-Quality linens - hand towels, bath towels, and washcloths for guestsbr- Roku TVbrbrPRIMARY BATHROOM:br-Newly renovated featuring spacious double sink vanitybr-Huge walk-in shower with glass sliding doorsbr-Spacious closet with luggage racksbrbrLOFTbr-The perfect spot to unwind for a game of Poker br-43in Roku TVbr-Bourbon barrel topsbr-Enjoy a glass of bourbon in the loungebrbrBEDROOM TWO:br-Equestrian-themed room with comfortable Novaform King mattress br-Spacious Walk-in closet for guest usebr-Lush linensbrbrBEDROOM THREE:br-Mint Julep-inspired room featuring a Novaform King bed br-Cozy linensbr-Full-length mirrorbrbrBEDROOM FOUR: br-The bourbon theme continues in this cozy bedroombr-Queen bed featuring a pillow-top mattressbrbrOUTDOOR SPACES:br-Enjoy time on the porch in the rocking chairs, with a stunning view of the rolling hills in Bourbon Country.br- Enjoy the 6-7 person hot tubbr- seating for 4 around the fire pit - Added fold out chairs for additional use.br- Weber gas grill for all your BBQ needs.br-Cornhole boards

Bourbon Trail Near Buffalo Trace-Hot Tub, Fire Pit, BBQ Grill

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$741.14

Escape to 19 acres on the Bourbon Trail, between Louisville & Lexingtonbr✔ Sleeps 12: 4 bedrooms, 5 beds and 3.5 bathroomsbr✔ Pool, hot tub, and firepitbr✔Speakeasy, game room, massage chair, poker tablebr✔ Dog & family friendlybr✔ 15–20 minutes from Buffalo Trace, Whiskey Thief, BulleitbrbrbrThe spacebrbrWelcome to Whiskey Business Retreat — your modern Kentucky getaway!brbr✔ Private 3500 sq ft home on 19 acresbr✔ Sleeps 12br✔ Massive Firepit seats 10br✔ Covered Hot Tubbr✔ In Ground Pool (Seasonal)br✔ Private Speakeasy with BYOB home bar, poker table, billiards, darts, arcade games, & morebr✔ Garage Game Roombr✔ Close to Buffalo Trace, Whiskey Thief Distilling, & Morebr✔ Fully Stocked Coffee barbr✔ Dog FriendlybrbrCheck-in after 4:00pm ET – Check-out before 11:00am ETbrbrAbout The Space:brWhiskey Business Retreat is your ideal home base for exploring the Kentucky Bourbon Trail. This spacious vacation rental sleeps up to 12 guests and is designed with comfort and convenience in mind — perfect for families, groups of friends, or bourbon enthusiasts.brbrEnjoy a fully equipped kitchen, family-friendly amenities, and plenty of space to relax after a day of tastings. We’re also dog-friendly, so your four-legged friends can join the adventure.brbrLocated just minutes from world-famous distilleries like Buffalo Trace, Whiskey Thief, and more, our retreat combines modern comfort with authentic Kentucky charm.brbrAmenities Guests Love:br➤ Seasonal In-Ground Pool & Covered Hot Tub – Cool off in the pool or unwind year-round in the hot tub, perfectly sheltered for all-weather relaxation.br➤ Private Speakeasy Bar – Mix up the perfect cocktail in our fully stocked bar — just bring the bourbon.br➤ Multiple game tables and over 1000+ classic arcade gamesbr➤ Starter supplies included to make your arrival that much smoother: paper towels, toilet paper, dishwasher pods, laundry pods, shampoo, conditioner, body wash.br➤ Local Insider Guidebook – Explore like a pro with our curated guide to the Bourbon Trail, Buffalo Trace, Whiskey Thief, and local attractions.br➤ Massive Outdoor Firepit – Gather around our 10-seat firepit with friends and family under the Kentucky night sky.br➤ Propane grill with propane included.brbrFront Porchbr➤ Relax in the classic rocking chairs on the spacious front porch while enjoying your morning coffee or an evening cocktail.br➤ The porch offers peaceful views of rolling Kentucky fields and farmland, creating the perfect serene backdrop.brbrKitchen and Diningbr➤ Fully Stocked Kitchen – Includes essentials for cooking and baking, even a crock pot, blender, air fryer, waffle maker, and more, plus silverware and dishware for the entire group.br➤ Coffee Bar – Keurig Duo, coffee grounds, K-cups, creamer, sugar, and more for easy mornings.br➤ Dining Table & Seating – Main table seats 10, with 4 additional seats at the breakfast bar and casual seating on the bay window bench.br➤ Starter Supplies – Paper towels, dishwasher pods, sponges, olive oil, and spices are ready for your arrival.br➤ Filtered Water Pitcher – Clean, chilled water available in the fridge.br➤ S’mores & Grill Fun – S’mores sticks and grill utensils included for outdoor cooking adventures.brbrLiving Roombr➤ Seating for your whole group.br➤ Cozy space with electric fireplace.br➤ 75 Smart TV to log into your own streaming services.br➤ Plenty of games you and your loved ones will enjoy.brbrSpeakeasybr➤ Private BYOB Speakeasy with pool table, 10-person poker table, lounge area, and a massage chair for ultimate relaxation.br➤ Fully stocked home bar: mini fridge, ice maker, and all the barware you need to mix your favorite drinks, including a whiskey smoker to make the perfect smoked Old Fashioned.br➤ Arcade fun: Buck Hunter and a 4-person gaming console with over 1,000 classic arcade games!br➤ 2 dart boards for friendly competition.brbrGarage Game Roombr➤ Pop-a-Shot, Air Hockey, and a Ping Pong TablebrbrOutdoor Spacebr➤ Seasonal In-Ground Poolbr➤ Massive firepit with seating for 10br➤ Covered 5-person Hot Tub on back patio with seatingbr➤ 2 acres of fenced yardbr➤ Adjustable Goalrilla Basketball Hoop in the drivewaybr➤ Golf Hitting Netbr➤ Propane Grill with Propane Tank includedbr➤ Al Fresco Dining, chaise lounge chairs, and a daybed to relax onbr➤ Pickleball Courtbr➤ Yard Games like bucket golf, lawn darts, cornhole, and more!brbrSleeping Accommodations & Bathrooms:brEvery bedroom comes ready for your stay with luggage racks, laundry baskets, hangers, and shelves for easy organization. Bathrooms are stocked with shampoo, conditioner, body wash, toilet paper, makeup towels, and hairdryers—and if you forget something, check the drawers; we’ve likely got you covered!brbrPrimary Suitebr➤ Comfortable King bed with the loved Helix Hospitality mattressbr➤ Soft sheets and comfy pillowsbr➤ Extra blanketsbr➤ Room darkening curtains that keep the room dark as neededbr➤ 65-inch Smart TV and electric fireplacebr➤ Mini Coffee Barbr➤ En Suite with large walk-in shower and large vanitybrbrGuest Bedrooms #1 & #2br➤ Each has Queen Beds with Helix Hospitality mattressesbr➤ Soft sheets and comfy pillowsbr➤ Extra throw blankets availablebr➤ 55” Smart TVsbr➤ Room darkening curtains that keep the room dark as neededbr➤ Bedroom #2 also has a workspace, perfect for catching up on workbrbrGuest Bedroom #4 (Basement)br➤ Two king beds featuring the loved Helix Hospitality mattressbr➤ Soft sheets and comfy pillowsbr➤ Extra throw blankets availablebr➤ Room darkening curtains that keep the room dark as neededbr➤ 75” Smart TV and electric fireplacebrbrExtra Sleeping Space: The living room can accommodate up to 2 additional guests on the provided queen air mattress.brbrExtra Sleeping Space for Dogs: The master closet has 2 dog beds for your furry companions to enjoy.brbrExtra Sleeping Space for Infants/Toddlers: The master closet has a pack n play stored inside. We recommend bringing your own sheets.brbrBathroomsbr➤ Master En-Suite Bathroom – Large vanity and walk-in shower with all toiletries provided.br➤ Upstairs Hall Bathroom – Large vanity, shower/soaking-tub combo, full toiletries, plus bath salts and bath bombs for a relaxing soak.br➤ Basement Bathroom – Updated vanity and walk-in shower with all essential toiletries included.br➤ Half Bath (Pool/Laundry Area) – Conveniently located near the pool and backyard, perfect for quick access while swimming or soaking in the hot tub.brbrParkingbrPlenty of room for your whole crew to park in our paved drivewaybrbrLocation -Driving Distances:brbrNearby Distilleries (Under 30 Minutes):br➤ Heaven's Door Distillery – 6 mi / 15 minsbr➤ Buffalo Trace Distillery – 7.6 mi / 20 minsbr➤ Whiskey Thief Distilling Co. – 7.7 mi / 20 minsbr➤ J. Mattingly 1845 Distillery – 8 mi / 20 minsbr➤ Bulleit Distilling Co. – 8.2 mi / 20 minsbr➤ Glenns Creek Distilling – 12 mi / 30 minsbr➤ The Stave – 13 mi / 30 minsbr➤ Jeptha Creed Distillery – 15 mi / 30 minsbr➤ Castle & Key Distillery – 17 mi / 30 minsbrbrNearby Wineriesbr➤ Talon Winery & Vineyardsbr➤ Lovers Leap Winerybr➤ Prodigy Vineyards & Winerybr➤ Equus Run Vineyardsbr➤ Rising Sons WinerybrbrNearby Golf Coursesbr➤ Juniper Hill Golf Coursebr➤ Capital City Golf Clubbr➤ Hickory Sticks Golf Coursebr➤ Kearney Hill Golf Clubbr➤ The Reserve at Boone’s TracebrbrFamily Fun & Recreationbr➤ Salato Wildlife Education Center – wildlife exhibits and walking trailsbr➤ Kentucky River Boat Tours – scenic river cruisesbr➤ Guist Creek & Marina – boating and lakeside activitiesbr➤ Shelby County Park & Recreation – playgrounds, trails, and sportsbrbrOther Local Attractionsbr➤ Frankfort (State Capital) – Explore downtown, the Kentucky State Capitol, Old State Capitol, Rebecca Ruth Candy Tours, shops, and restaurantsbr➤ Lexington & Surrounds – Keeneland Race Course, The Kentucky Castle, Lexington Distillery Districtbr➤ Louisville – Louisville Slugger Museum & Factory, Churchill Downs, Louisville ZoobrbrGrocery & Essentialsbr➤ Walmart Supercenter and Kroger – just a short drive away for all your shopping needsbrbrGuest have access to the entire property and all of its amenities!brbrA code for the electronic door lock will be sent prior to check-in. Guests are welcome to check-in anytime after 3pm.brbrWe respect your privacy and want you to feel at home during your stay. We are available by phone, text, or VRBO messaging for any questions or assistance before or during your visit.brbrWe do not live on-site, so you’ll have full access to the entire property and all amenities, but we’re just a message away if you need recommendations, guidance on the house, or anything else.brbrGrill: Propane provided for the grill.brbrCoffee & Tea: A starter set of K-cups, ground coffee, and tea provided.brbrHot Tub & Pool: No glass or food in the hot tub or pool. Do not use the hot tub if you have consumed alcohol or are pregnant. Use at your own risk.brbrSecurity Features:brRing doorbell camera at the front doorbrRing floodlight camera above the back patio facing the pool areabrRing floodlight camera above the garage door facing the drivewaybrbrTravel Insurance: We recommend purchasing travel insurance to protect against unforeseen weather or circumstances.

Kentucky Derby Stay: Bourbon Trail Home w/ Pool, Speakeasy, Dog-Friendly, Games

Frankfort, Kentucky, United States

4

Bed

Bath

12

Sleeps

$239.92

Lake house ✔️ brBourbon Trail ✔️ brHorse country ✔️ brbrYou’re sure to fall in with lake views, cozy bedding, modern decor & a well-stocked kitchen. Located in the capital on the Ky Bourbon Trail, this peaceful Lakehouse is sure to be the perfect getaway for couples, friends & families alike! Minutes to several distilleries, 10 mins to the Capitol, 30 mins to Lexington. Pets are allowed for $150 per stay.brbrWe live nearby & are available if needed, but generally do not personally interact with guests.brbrThis is a row of 4 adjoined townhomes overlooking a small lake, located in a residential neighborhood. Please be respectful of our neighbors.brbrGuests have access to the entire home.brbrThis is a split-foyer townhome. The lower level features a living room with an electric fireplace, a 55” Smart TV, fully-stocked kitchen, a renovated half bath & dining area. Outside, you can relax on either of our two decks & enjoy the sounds of wildlife on the lake, cast your own line (bring your poles & kayaks!) or enjoy a cocktail after a day on the Bourbon Trail. We also provide a Weber charcoal grill, if you’re in the mood to BBQ. Guests will need to login to their own streaming services on the TVs. brbrUpstairs, you’ll find 2 bedrooms (one king bed & one queen), one full bathroom (shower only) & full laundry. The spacious primary bedroom features a king bed, a 42” Smart TV, desk, reading lamps (with USB chargers), dresser, luggage rack & closet. The 2nd bedroom features a queen bed, blackout curtains, reading lamps (with USB chargers), dresser, luggage rack & closet. A renovated bathroom w/ a glass-shower enclosure & a new washer & dryer complete the upstairs.brbrYour car, Uber, car rental or taxi is best.brbrThere are only 2 dedicated parking spaces available in front of the townhouse. Please try to park directly in front - leaving 2 spaces to your left & 4 spaces to your right. There is additional street parking available for more than 2 cars.brbrA processing fee will be deducted from all refunds, regardless of when you cancel the reservation. This fee is charged by the payment processor - the hosts do not keep any of this fee! We simply cannot afford to pay $ to the credit card companies & payment processors because a guest changes their mind. Thank you for understanding.

Bourbon Trail Lakehouse - Pet Friendly!

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$222.96

Experience Frankfort like a local in this 3-bedroom house. This charming property features 2 queen beds and 1 twin bed, perfect for a family or group of friends. With amenities like WiFi, AC, and a fully equipped kitchen, guests can relax and unwind after a day of exploring. The 2 bathrooms with showers and hair dryers add convenience to your stay. Feel free to reach out to us during your stay - we're happy to suggest local spots and restaurants to check out. Right on the Bourbon Trail starting at Buffalo Trace Distillery and making your way to either Woodford Reserve, Makers Mark, Wild Turkey, Four Roses and many other Distilleries on the Trail. Conveniently located between Lexington and Louisville for local Horse attractions such Keeneland, Kentucky Horse Park and Churchill Downs.

Shire-Southern-Comfort quiet 3-bedroom house w/WiFi and AC in heart of downtown

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$429.74

Prohibition-Era Luxury on the Kentucky Bourbon TrailbrbrStep into a modern retreat with a vintage soul at this restored 3BR, 2.5BA getaway, where original details, moody lighting, and jazzy décor create a uniquely immersive experience. Perfectly located in the heart of Kentucky’s capital, this home is 1.5 miles from Buffalo Trace and minutes from many iconic distilleries. An ideal hideaway for Bourbon Trail explorers, couples’ trips, girls’ weekends, and sophisticated group getaways.brbrStylish, Spacious & Built for RelaxationbrSleeps 8 comfortably with beautifully designed bedrooms and luxe bathrooms.br• Fully equipped kitchen for cocktails and chef-inspired mealsbr• Cozy, moody living spaces perfect for unwinding after tastingsbr• Private hot tub for nighttime soaks under the starsbr• Game room with a full-size pool tablebr• Outdoor fireplace table for fireside eveningsbrbrUnbeatable Location for Bourbon Loversbr• 1.5 miles to Buffalo Tracebr• Minutes to Castle & Key, Whiskey Thief, Woodford Reserve, Four Roses and morebr• Walk to the Kentucky State Capitol, local bars, restaurants and coffee shopsbr• Close to Kentucky Riverboat Tours for a scenic way to explorebr• Short drive to Kentucky State University and vibrant downtown FrankfortbrbrFor the Adventurers & ExplorersbrDiscover nearby wineries, riverfront paths, historic sites, and hidden gems such as the Kentucky Bourbon House. Explore downtown Frankfort’s boutiques, antique stores, art shops, and locally loved eateries.brbrYour Private, Peaceful Bourbon RetreatbrAfter a day of distillery tours, return to tranquility and moody luxury. Relax in the hot tub, enjoy a game of pool, or unwind by the outdoor fire table. Whether you're here for a weekend or a longer stay, this home offers the perfect blend of comfort, charm and character.brbrYour Kentucky Bourbon experience starts here—book your stay today!

Bourbon Trail 3-bedroom house in Frankfort 1.5 Miles to Buffalo Trace

Frankfort, Kentucky, United States

Bed

2

Bath

8

Sleeps

$506.89

Unwind on the Bourbon Trail in this renovated 4-bed, 3-bath Frankfort home, perfect for 8 guests. Just minutes from legendary distilleries, this family-friendly retreat features a private hot tub, a cozy fire table, and king beds in every room. Enjoy modern comforts and a stylish design, all within a short walk to historic downtown. Your ultimate Kentucky getaway awaitsbr Buffalo Trace – 2 miles awaybr Downtown Frankfort - under a mile away. br Four Roses - 10 miles awaybrbrWe prioritize your privacy and offer a seamless self-check-in experience. While we won't be on-site during your stay, we are always available and happy to assist with any questions or recommendations via the messaging app. Your comfort is our top priority.brbrLocated in a quiet, historic neighborhood, this home offers a perfect blend of charm and convenience. Just a short walk to downtown Frankfort, you'll find local shops, restaurants, and the Kentucky State Capitol. The area is peaceful and family-friendly, with tree-lined streets and a welcoming atmosphere. Explore nearby parks, enjoy scenic views of the Kentucky River, or take a short drive to discover the famous Bourbon Trail. Whether you're here for relaxation or adventure, the neighborhood provides the ideal setting to enjoy all that Frankfort has to offer.brbrbrGuests will have private access to the entire home and its amenities, including the backyard with the hot tub and fire table. Enjoy seamless self-check-in with a smart lock; your unique code will be sent before your arrival. The only area that is not accessible is a locked owner's closet located upstairs. Ample street parking is available directly in front of the property.brbrModern Comforts with Historic Flair – Renovated in 2021br● 4 Bedrooms – (1 downstairs, 3 upstairs) | All King Bedsbr● 3 Full Bathrooms – Including one with double showersbr● Pack & Play available for little onesbr● Fire Table for cozy outdoor eveningsbr● Fully Stocked Kitchen – Cookware, Crock-Pot, Coffee Barbr● Smart TVs in Living Room + Bedroomsbr● Washer & Dryerbr● Premium Linens & Green Tea Cooling Mattressesbr● Board Games for family funbrbrNearby Attractions & Distances: Your bourbon journey begins at your doorstep, with legendary experiences waiting just minutes away:brbrBourbon Trail & Distilleriesbr Buffalo Trace (6 min) – Legendary bourbon and rich history in every pour.br Four Roses (20 min) – Classic Kentucky recipes, crafted to perfection.br Castle & Key (20 min) – Small-batch spirits in a stunning castle setting.br Woodford Reserve (25 min) – A scenic distillery known for refined bourbon.br Three Boys Farm (25 min) – Farm-to-bottle craftsmanship with big flavor.br Whiskey Thief (30 min) – Bold, unfiltered spirits with local character.brbrLocal Treasures (Walkable)br Downtown Frankfort – (10 min) – Eateries, shops, and small-town charm.br Kentucky State Capitol – (10 min) – Impressive architecture and historic significance.br Rebecca Ruth Candy – (8 min) – Birthplace of the bourbon ball—treat yourself!br Capital City Museum – (10 min) – Explore the stories behind Kentucky’s capital.br History Center – (8 min) – Dive into the state’s most memorable moments.brbrNature & Recreationbr Cove Spring Park – (5 min) – Peaceful trails and scenic views.br Salato Wildlife Center – (12 min) – Get up close with native wildlife.br Prodigy Vineyards – (15 min) – Local wines and beautiful countryside vibes.brbr☆☆ Living Room ☆☆brThe mid-century inspired living area offers a stylish yet cozy setting to unwind. A plush sectional provides ample seating and can even accommodate an extra guest, while a pair of leather swivel chairs add a touch of flair and comfort. A 65 Smart TV is perfect for movie nights or catching up on your favorite shows. Just off the living space, a dining area invites you to gather for meals or games, and the nearby kitchen coffee bar makes it easy to refuel any time of day.brbr☆☆ Bedrooms ☆☆brEach of the four bedrooms has been designed with rest and relaxation in mind. Every room features a king-sized bed with a cooling green tea memory foam mattress, premium linens, and blackout curtains for uninterrupted sleep. Nightstands, reading lamps, and white noise machines that offer gentle nature and rain sounds add to the tranquil ambiance. With 55 Smart TVs in each room, guests can unwind in comfort and privacy.brbr☆☆ Kitchen ☆☆brBright and spacious kitchen is a chef’s delight, equipped with stainless steel appliances, a full array of pots, pans, and a convenient Crock-Pot for easy meal prep. The star of the space is the coffee and tea bar, fully stocked with coffee, creamers, honey, sugar, and a variety of teas to start each morning right. Designed with an open layout, the kitchen flows seamlessly into the living room, making it perfect for entertaining or staying connected with family and friends while cooking. Whether you're preparing a full meal or just enjoying a morning brew, this kitchen has everything you need!brbr☆☆ Outside Space ☆☆brStep outside and enjoy the perfect blend of relaxation and entertainment. The front porch features cozy rocking chairs, ideal for sipping a drink and watching the world go by. In the backyard, unwind in the 6-person hot tub, or gather around the fire table with swiveling chairs for a warm, inviting atmosphere. For those who love to grill, a fully equipped grill with all the necessary tools is ready for your next barbecue. Whether you're soaking up the sun or enjoying an evening under the stars, this outdoor space has everything you need to make the most of your time outside.brbr☆☆ Dog-Friendly ☆☆brWe welcome one well-behaved dog under 50 pounds with a $100 non-refundable pet fee. Please bring your own dog bed and help us protect the furnishings. We kindly ask that you clean up after your pet in the yard to keep the outdoor space clean and enjoyable for everyone.brbrMany of Frankfort’s most popular destinations are within walking distance, including restaurants, shops, and historical landmarks. A car is helpful for exploring the surrounding distilleries and natural areas, and rideshare services like Uber are available in the area.brbr● Check-in is any time after 4:00 PM.br● The fireplace is for decorative purposes only and is not operable.br● The smart thermostats are set to maintain a comfortable 70 degrees.br● Portable heaters are provided to use when its unusually cold outside. br● The rear door has a manual lock; please ensure it is locked for your security.br● The fence door must be kept closed at all times.br● Trash cans are located on the right side of the property.br● For your security, a Ring doorbell camera is at the front door and another camera is on the rear door, both recording audio and video. These cameras do not have visibility into any interior spaces or the private backyard hot tub area.

Bourbon Basecamp Hot Tub Mins to Trace Four Roses

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$645.69

Nestled along the Kentucky River, this riverfront retreat blends historic charm with modern comfort. Walk to downtown Frankfort, then relax in the private hot tub with river views. Just 2.5 miles from Buffalo Trace Distillery and close to Woodford Reserve Distillery, Four Roses Distillery, Wild Turkey Distillery, and Castle & Key Distillery. Professionally cleaned, fully stocked, and done right.

Walk Downtown Frankfort Hot Tub 2mi Buffalo Trace

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$449.0

Spacious 4BR/4BA Luxury Home – Perfect for Bourbon Trail and Keeneland Trips!brbrWelcome to your stylish and spacious home-away-from-home in the heart of Frankfort, Kentucky – the perfect base for exploring the Bourbon Trail, races at Keeneland, or visiting the State Capitol.brbrCentral Location –br• 5 mins to Buffalo Trace Distillerybr• 5 mins to downtown Frankfort and Capitolbr• 35 mins to Keeneland and Lexingtonbr• Easy access to the full Kentucky Bourbon Trail

Bourbon Trail Getaway - 3 miles Buffalo Trace

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$1172.74

Welcome to Proof of Life by LIVE & TRAVEL HOMES! Where bourbon flows, golf swings & laughter echoes. With a speakeasy, golf sim, sauna, hot tub, fire pit, game & theater rooms, this is where you press pause -- and play. From the moment Spirit greets you & Baby Thunder stands guard by the flames, one thing is clear: You’re alive, and this is living. Reset, reconnect, and raise a glass: life is worth savoring. Bourbon country has never felt more personal. Minutes from Buffalo Trace & Castle & Key.brbrThe spacebrOVERVIEWbrWelcome to Proof of Life — a one-of-a-kind Bourbon Trail retreat where timeless Kentucky charm meets modern luxury and unforgettable entertainment.brbrYour stay includes:br✔ The Heart of Proof – elegant main residence + Speakeasy Annexbr✔ The Playhouse – private theater, game room & golf simulator loungebr✔ Barrel sauna, hot tub & outdoor firepit gathering spacebr✔ Sleeps 14 comfortablybr✔ EV charger & parking for 6 vehiclesbrbrPerfect for bourbon trail trips, celebrations, retreats, and unforgettable group stays.brbrSLEEPING ARRANGEMENTS (Sleeps 14)br• 4 King bedsbr• 2 Queen bedsbr• Queen sofa bedbrbr✔ 7 beds total for flexible comfortbrbrWHAT GUESTS LOVE br Authentic Bourbon Trail ExperiencebrbrImmerse yourself in Kentucky culture with thoughtfully curated décor and gathering spaces inspired by bourbon heritage and Bluegrass traditions.brbrThe Playhouse: Private Entertainment HavenbrA detached entertainment retreat guests rave about:br✔ Golf simulator & putting green loungebr✔ Private theater with reclining seatingbr✔ Game room with arcade & foosballbr✔ Turf-lined social lounge spacebrbrPerfect for friendly competition and unforgettable nights.brbr Speakeasy Annex & Bourbon Loungebr✔ Pool table & shuffleboardbr✔ Historic bourbon & prohibition décorbr✔ Lounge seating & large TVbr✔ Perfect space for evening cocktails & conversationbrbr Outdoor Haven & RelaxationbrbrEnjoy memorable evenings outdoors:br✔ Barrel sauna & hot tubbr✔ Firepit with Adirondack seatingbr✔ Outdoor pavilion lounge & diningbr✔ Gas grill & pizza ovenbr✔ Outdoor showerbrbrIdeal for relaxing after distillery tours or gathering under the stars.brbrSPACIOUS GATHERING AREASbrbrDesigned for connection and comfort:br✔ Elegant living room with fireplacebr✔ Bourbon lounge & conversation spacesbr✔ Dining seating for large groupsbr✔ Cozy nooks for relaxing & socializingbrbrFULLY EQUIPPED KITCHEN & COFFEE BARbr✔ Double ovens & fully stocked kitchenbr✔ Coffee bar with Keurig Duo, French press & cold brewbr✔ Cooking essentials & entertaining-friendly layoutbrbrBEDROOMS & BATHSbr✔ 4 full bathroomsbr✔ King suite & spa-inspired primary bathbr✔ Spacious, private sleeping areasbr✔ Laundry facilities availablebrbrFAMILY & GROUP FRIENDLYbr✔ Pack ’n Play & highchairbr✔ Arcade games & interactive spacesbr✔ Multiple gathering zones for all agesbrbrEXTRA CONVENIENCESbr✔ EV charger (Level 2)br✔ Dedicated workspacesbr✔ Outdoor lounge & covered pavilionbr✔ Photo-worthy bourbon barrel displays & décorbrbrProof of Life is more than a stay — it’s a destination experience blending bourbon culture, luxury comfort, and unforgettable entertainment.brbrGuest accessbrGuests will have access to the whole home.brbrOther things to notebr◘ RENTAL AGREEMENTbrTo finalize your reservation, we require a signed rental agreement. This confirms that you understand and agree to our policies. Without it, the booking will be canceled.brbr◘ TRAVEL INSURANCEbrTravel Insurance is highly recommended: There are NO REFUNDS for transportation disruptions, event cancellation, unexpected illness or injury, weather or natural conditions, jury duty or court appearances, or any unforeseen events beyond our control or responsibility.brbr◘ HOUSE RULESbrPlease take a moment to read through our House Rules. They’re designed to help keep our guests safe, protect the property, and ensure the best possible experience.

Bourbon Trail Estate, Golf Sim, SpeakEZ, Sleeps 14

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$682.25

The Ann Street Retreat is a charming, newly remodeled historic home in downtown Frankfort, Kentucky. This 4-bedroom, 3.5-bath retreat features three king beds, one queen, and four twin beds, offering ample space for guests. The spacious kitchen is perfect for gathering after a day of bourbon tastings. Outside, unwind in the hot tub or by the firepit in the professionally landscaped backyard. A true bourbon lover’s escape, blending history, comfort, and Southern hospitality.brbrProfessionally managed, our team is here to support you with any needs or local recommendations throughout your stay. Enjoy a seamless, automated check-in experience, and reach out anytime to take advantage of our personalized concierge services.brbrAnn Street Retreat sits in the heart of downtown Frankfort, nestled within the Old Statehouse Historic District—an area filled with charming 19th‑century architecture and leafy, walkable streets. The district borders Broadway, St. Clair, High, Blanton, and Ann Streets, and contains 74 historic buildings including the Old State Capitol and Governor’s Mansion. This location offers a true capital‑city vibe: government offices, museums, and parks are just steps away. You're within a stroll of the Kentucky State Capitol, state agency buildings, and serene historic parks. Don't forget, you are also just steps away to multiple local eateries and coffee shops. brbrGuests will have full access to this spacious and historic single family home. Don't forget we offer a private backyard oasis and parking. brbrWelcome to The Ann Street Retreat — your stylish, spacious, and perfectly located escape in the heart of downtown Frankfort, Kentucky. Whether you're planning a weekend getaway, a Bourbon Trail adventure, or a group stay with family and friends, this historic 4-bedroom, 3.5-bath home offers the comfort, charm, and convenience you’re looking for.brbrWhat You’ll Love:brLocation, Location, Location: Nestled in the heart of the Old State Capitol District, you’re just steps from museums, shops, restaurants, the Kentucky River, and iconic landmarks like the Capitol building.brbrRoom for Everyone: With 4 spacious bedrooms (3 kings, 1 queen, and 4 twins), the home comfortably sleeps up to 12 guests—ideal for families, friend groups, wedding parties, or corporate travelers. We have 3 TWIN Size roll away cots that can be moved or housed anywhere in the home. brbrHistoric Charm Meets Modern Comfort: Newly renovated, the home blends original architectural details with contemporary finishes, including a fully updated kitchen, elegant bathrooms, and cozy gathering spaces.brbrWalkable Downtown Access: Park your car and enjoy walking distance to local eateries, cafés, wine bars, boutiques, and riverfront trails.brbrBourbon Country Basecamp: Only minutes from the world-famous Buffalo Trace Distillery and a short scenic drive to Woodford Reserve, Castle & Key, and more.brbrGreat For:brFamily vacations or reunionsbrBourbon Trail toursbrWedding guests and bridal partiesbrGirls’ trips or couples’ retreatsbrBusiness travelers and workcationsbrbrBonus Features:brPrivate garden and patio space for relaxing eveningsbrFree, convenient on-site parkingbrSmart TVs, fast Wi-Fi, and self-check-inbrLocal artwork and curated décor to enhance your staybrbrWhy Guests Keep Coming Back:br“Even better than the photos!”br“Perfect for our group — so much space and charm.”br “Amazing location — walked everywhere downtown!”br“Sparkling clean, beautifully decorated, and super comfortable beds.”brbrReady to explore Kentucky’s capital in comfort and style brBook The Ann Street Retreat today and make your next stay unforgettable.brbrBring your own vehicle to make the most of exploring Central Kentucky’s iconic bourbon distilleries, scenic byways, and hidden gems—many are just a short drive away. When you’re ready to slow down, park with ease and enjoy the charm of downtown Frankfort on foot, with shops, restaurants, and historic landmarks all within walking distance.

Ann Street Retreat

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$470.64

If you like bourbon, you will LOVE this place. Perfect for families, friends, bourbon hunters, and bachelor/ettes! You will find a hidden speakeasy lounge if you look hard enough! Come stay with us!!!

Van Winkle's Secret/Speakeasy (Hidden Room)

Frankfort, Kentucky, United States

Bed

Bath

8

Sleeps

$803.81