Vacation Rentals By Owner In Frankfort, KY

Maya’s Bluegrass Resort | 7,500 Sq Ft Luxury Creekside Retreat | Speakeasy, Theater, Hot Tub, Sauna | Near Bourbon TrailbrbrWelcome to Maya’s Bluegrass Resort, a one-of-a-kind 7,500 sq ft luxury estate in Kentucky’s Bluegrass region, designed for unforgettable group getaways, Bourbon Trail adventures, family reunions, retreats and milestone celebrations.brbrTucked beside a peaceful creek and just minutes from world-famous distilleries, this private estate blends resort-style amenities, elevated interiors, immersive entertainment and serene natural beauty—creating a stay that feels more like your own exclusive boutique resort than a traditional vacation rental.brbrStart your mornings with premium coffee overlooking the creek, spend your days exploring the Kentucky Bourbon Trail, historic towns, wineries, and scenic countryside, then return to evenings of bourbon tastings in your private speakeasy, movie nights in the theater, hot tub soaks under the stars and fireside conversations with the people who matter most.brbrWhether you're planning a Bourbon Trail getaway, corporate retreat, bachelor/bachelorette weekend, family vacation or celebration, Maya’s Bluegrass Resort was thoughtfully designed to bring people together in comfort, style and unforgettable luxury.brbr✨ A True Private Resort ExperiencebrSpanning three expansive levels, this luxury creekside retreat offers a rare combination of sophisticated design, spacious gathering areas, wellness amenities and unique entertainment spaces for guests of all ages.brbrFrom the hidden speakeasy bourbon lounge to the glow-in-the-dark disco game cave, every room is intentionally curated to create moments your group will remember long after checkout.brbr Signature Amenities & Experiencesbr★ Private Creekside Estate: Enjoy peaceful privacy surrounded by nature, with multiple decks and outdoor spaces overlooking the creek.br★ Speakeasy Bourbon Lounge + Karaoke Bar: Create your own private bourbon-tasting experience, mix craft cocktails, sing karaoke, and enjoy unforgettable evenings without leaving home.br★ Luxury Home Theater + Hidden Adventure Nook: Perfect for cinematic movie nights, cozy lounging, and a surprise kid-friendly space younger guests will love.br★ Glow Disco Room & Game Cave: A high-energy entertainment zone featuring glow-in-the-dark design, arcade-style fun, and immersive experiences for all ages.br★ Resort-Style Outdoor Living: Relax in the hot tub, gather by the fire pit, grill on the BBQ patio, and enjoy creekside dining and lounging.br★ Wellness & Relaxation Suite: Recharge with a private sauna, massage space, and fitness area—ideal for a spa-inspired retreat experience.br★ Designer Dining Hall & Elegant Living Spaces:Beautifully curated gathering areas designed for group dinners, celebrations, meaningful conversations, and elevated comfort.br★ Music Lounge & Creative Studio: Enjoy a piano, guitar, and curated instruments for spontaneous music, creativity, and connection.br★ Gourmet Coffee & Bourbon Bar: Begin the day with a premium coffee experience and end it with curated bourbon tastings.br★ Family-Friendly Luxury: Indoor glamping tent, board games, playful spaces, and thoughtful touches for families and kids.br★ Pet-Friendly Stay: Well-behaved pets are welcome, so the whole family can enjoy the getaway.br★ Ample Parking for Up to 10 Vehicles: Ideal for large groups, retreats, and approved celebrations.brbr Your Perfect Bourbon Trail Home BasebrLocated near some of Kentucky’s most iconic bourbon destinations:brWhiskey Thief – 8 minbrBuffalo Trace – 13 minbrBulleit – 18 minbrCastle & Key – 19 minbrWild Turkey – 23 minbrWoodford Reserve – 23 minbrFour Roses – 24 minbrPlus nearby wineries, scenic drives, historic towns, restaurants, and adventure experiences.brbr Nearby DestinationsbrKeeneland – 30 minbrThe Kentucky Castle – 30 minbrBlue Grass Airport / LEX – 35 minbrLexington – 40 minbrLouisville / SDF – 45–50 minbrChurchill Downs – 50 minbrbr Perfect Forbr✔ Bourbon Trail groupsbr✔ Luxury family vacationsbr✔ Corporate retreatsbr✔ Bachelor / bachelorette weekendsbr✔ Approved weddings & celebrationsbr✔ Multi-generational gatheringsbr✔ Wellness and relaxation retreatsbr✔ Large group getawaysbrbr Optional Concierge ExperiencesbrEnhance your stay with curated add-ons:br✔ Grocery pre-stockingbr✔ Private chef experiencesbr✔ Custom Bourbon Trail toursbr✔ Chauffeur / transportation coordinationbrbr Where Luxury Meets ExperiencebrAt Maya’s Bluegrass Resort, every detail is designed to deliver more than just a place to stay. This is a curated experience of connection, celebration, relaxation, and elevated Kentucky living.brbrFrom speakeasy nights and creekside mornings to hot tub soaks, theater evenings, and fireside memories, this private estate is built for unforgettable stays.brbr✨ One-of-a-kind luxury Bourbon Trail estates book quickly — reserve your dates today.brbrELEGANT BEDROOM LAYOUTbr★ Main Level:brBedroom 1 – Kentucky Nature: King + crib + ensuitebrBedroom 2 – Noah’s Arc: King + ensuitebrBedroom 3 – Bluegrass Music: 2 Queens + ensuitebrbr★ Second Level:brBedroom 4 – Derby Room: 2 Kings + ensuitebrBedroom 5 – Mammoth Cave: King + ensuitebrBedroom 6 – Free Spirit: 2 QueensbrBourbon Family Room – Pull-out sectional sofabrPrivate Study/Library – Pull-out sofabrbr★ Third Level:brBehind Theater – Additional pull-out sofabrbr★ Gourmet Kitchen & Elegant DiningbrCreate unforgettable meals in the fully equipped chef’s kitchen featuring:br- Premium appliances: full oven, large fridge/freezer, dishwasher, microwave and ice-makerbr- Exotic coffee bar: Keurig, French press, blender and premium coffee/condimentsbr- Elegant serve ware and high-end cookwarebrbr★ Enjoy:br- Formal dining for 10 at the custom tablebr- Casual dining at the kitchen island (seats 4)br- Al fresco meals on the outdoor dining patio (seats 10)brbr★ Refined Living Spaces for Every OccasionbrMain Living Room: Luxe seating, soaring ceilings, and a 65 smart TVbrSecond-Level Bourbon Lounge: Rich textures, additional 65 TV, ideal for relaxing or entertainingbrbr★ 2026 MUST-ATTEND EVENTS NEAR OUR PROPERTYbrbrRailbird Music Festival — June 6–7, 2026 (Lexington)brFestival of the Bluegrass — June 12–14, 2026brBluegrass Music Festival — June 10–13, 2026brBoonerang Music & Arts Festival — June 19–21, 2026brHeritage Day & Kiln Opening — June 27, 2026 (Versailles)brSummer winery & castle events — All JunebrBluegrass 10,000 — July 4, 2026 (Lexington)brFrankfort River Blast Fireworks — July 4, 2026brFourth of July parades & festivals — All CitiesbrBreyerFest — July 10–12, 2026 (KY Horse Park)brWoodland Art Fair — Aug 15–16, 2026 (Lexington)brBourbon & Barbecue Festival — Aug 22–23, 2026 (projected)brLate-summer wine trail events — All Augbr58th Annual Frankfort Fall Festival — Sept 5–7, 2026brJosephine Sculpture Park Fest — Sept 5–6, 2026 (projected)brKentucky Bourbon Festival — Sept 10–13, 2026brVersailles Twilight Festival — Sept 19, 2026brWine & Ale Walk (Frankfort) — Sept 27, 2026brCapital City Blues & River Festival — Sept 26–27, 2026brEarly fall wine & horse farm events — Sept Month-LongbrKeeneland Fall Meet — Oct 3–24, 2026brBourbon on the Banks — Oct 3, 2026 (Frankfort)brJack-o-Lantern Spectacular — Oct 1–31, 2026 (Kentucky Castle)brVersailles Fall Festival — Oct 17–18, 2026brPeak Fall Colors — Oct 12–25, 2026brOktoberfest weekends — All OctoberbrSouthern Lights Holiday Festival — Nov 27–Dec 31, 2026 (KY Horse Park)brFrankfort Candlelight Weekend — Nov 27–28, 2026brThanksgiving Weekend Events — Nov 26–29, 2026brHoliday markets & winery lights — Late NovemberbrChristmas in Versailles — Dec 5–6, 2026brLexington Christmas Parade — Dec 5, 2026 (projected)brKentucky Castle Holiday Market — Dec 12–13, 2026brSanta Train & Holiday Railroad Rides — Dec 5–6 & Dec 12–13, 2026brDistillery candlelight tours — All DecbrNew Year’s Eve Celebrations — Dec 31, 2026brbrNOTE:br1. Must be 25+ to book.br2. Please review house rules. Guests must e-sign our rental agreement and submit a $500 security hold (processed via OwnerRez). The hold is placed 2 days before arrival and released 7 days after checkout if no damages.br3. Strict cancellation policy for Derby & Bourbon & Beyond dates.br4. No unapproved visitors.br5. Exterior cameras only (front parking area). No interior or backyard cameras.br6. No early check-ins/late check-outs for same-day turns.br7. When available: Early CI/Late CO = $100 (up to 2 hrs), $250 (2–4 hrs), or full night rate (4+ hrs).br8. For non-Airbnb bookings, cancellations incur a 3% Stripe processing fee.br9. We're pet-friendly (up to 2 dogs; fees apply)brbrbrPLEASE REVIEW THE HOUSE RULES BEFORE BOOKING. THANK YOU!!

Creekside Luxury Hot Tub Firepit Sauna Themed Spaces Speakeasy

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$416.52

Top of the Rock — Your Kentucky GetawaybrbrExperience Kentucky like never before at Top of the Rock, a private lower-level mother-in-law suite with million-dollar views. Perched above historic Frankfort, this one-of-a-kind stay overlooks the Capitol Building, Kentucky River, downtown Frankfort, Kentucky State University, and the rolling hills beyond — a stunning backdrop for your getaway.brbrAn Unbeatable LocationbrbrIdeally located just 50 miles from downtown Louisville and only 35 minutes from Lexington and Keeneland Race Course, Top of the Rock places you right in the heart of bourbon country, horse country, and Kentucky’s best experiences.brbrA True Bourbon Country EscapebrbrWake up to the unmistakable aroma from nearby Buffalo Trace Distillery and spend your days exploring the world-famous distilleries along the Bourbon Trail. After a day of touring, return to your private deck, pour a cocktail, and take in a breathtaking Kentucky sunset.brbrRelaxation & ComfortbrbrUnwind in the outdoor hot tub with panoramic views of Frankfort’s most iconic landmarks. The suite is thoughtfully designed for comfort, privacy, and a true home-away-from-home feel.brbrTop of the Rock is a private, fully separated lower-level suite within our home, and we (the owners) live upstairs. While you’ll have your own entrance and space, you may occasionally hear normal household activity — most guests find this minimal and appreciate the added sense of security and responsiveness during their stay.brbrWhether you're here for bourbon, horse racing, a UK getaway, or simply to relax and enjoy the view, Top of the Rock offers a uniquely Kentucky experience you won’t forget.

TOP OF THE ROCK Hot tub EV Charger Buffalo Trace Bourbon Trail Fire Pit

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$459.35

Welcome to The Barrel & Stone Estate, a lovingly restored 1920s home, where timeless character meets modern luxury. Whether you're here for a getaway, a family trip, or a fun friends weekend, this spacious retreat offers everything you need to relax & unwind. This house is conveniently located minutes from several of the most famous Bourbon Distilleries in the country. It is less than an hour's drive from both Lexington and Louisville. This is a perfect location to see Kentucky at its best.

Dwntwn/Renovated/Backyard/Fire-Pit/Hot Tub

Frankfort, Kentucky, United States

4

Bed

3

Bath

8

Sleeps

$226.84

NO ADDITIONAL FEES!brbrThis NEWLY remodeled house is located right in the middle of Kentucky's Bourbon Trail and right on the banks of the beautiful and popular Elkhorn Creek. Just up stream from the non open to the public Jim Beam's Old Granddad Plant, and only a few miles from Buffalo Trace Distillery, Woodford Reserve Distillery, Castle and Key Distillery and Glenn's Creek Distillery. This location makes this house the perfect gathering spot for your bourbon themed vacation. brbrThis home is perfect for two couples, a family of 4 to 6 or one couple looking for plenty of space. Sit on the covered front porch and enjoy a coffee or cocktail while listening to the sound of the Macklin Dam on Elkhorn Creek. The living area is great for entertaining, with plenty of space for everyone to gather around. The house has an antique game table that for many years was the centerpiece of the Mayflower Hotel and Fish Camp on Elkhorn Creek, a historic travelers rest, before being torn down in the 1970's. There is also a foosball table to enjoy.brbrOne of the centerpieces of this home is the beautiful live edge bar, where you can kick back wit friends and enjoy one of our cocktail recipes hanging on the wall. We provide you the mixing essentials and most of the ingredients... you provide the good stuff! The bar is part of the large kitchen with an even larger dining room table, with plenty of room for everyone in your group.brbrTwo large bedrooms are why the house has two master suites. One room has a private bathroom, while the other shares a bathroom with the kids bunk room. Each room has a queen bed and antique dressers and tables. Each bathroom is recently remodeled and boast oversized tile showers, comfortable vanities and a toilet. Both bathrooms have tile floors. The 3rd room has a full-size futon, which if you book more than 2 couples or children, we will have made up for you as a bed. This room has old school games to keep the kids entertained and a foosball table. The home is located on a main road, not a side street, so if you are a light sleeper, you may hear the sounds of the cars going by. Most of our guests have made no mention of it being obtrusive (just being honest!). brbrThe back of the house boasts plenty of parking, even from vehicles with trailers, RV's, etc. The home is built into what was a church parking lot, so when we say there is parking room... there is parking room! At the back of the parking area is a great sitting area on the banks of the Elkhorn Creek. Bring a fishing pole or use one of the ones provided, and try your hand at landing the strong fighting smallmouth bass. The spot is also great for launching or landing your canoe or kayak. This spot would be the end of a 9 mile trip from Switzer Covered Bridge, or the beginning of a trip 7 miles through Class II whitewater. Other Class I stretches begin farther down stream. brbrThe Elkhorn Creek is the most popular paddled stream in the state of Kentucky. It is also considered the best small mouth bass fishing stream in the state. Both of these activities can be enhanced by a trip to Canoe Kentucky, located only a few miles away. Your stay at this house allows you unparalleled access to the upper Elkhorn, a Class II moving water section. Launch your kayaks and canoes directly from the property! If Class II water is not your thing, there are nearly 20 miles of Class I water as well, some sections ending at the house, some farther down stream.brbrOn top of this great location, we, the hosts, are Kentucky Bourbon Trail experts. We have been working in the Bourbon Trail world as guides for over 20 years! All this knowledge allows us to offer those booking this house to be given exclusive planning itineraries, tips and bourbon secrets. We are also very knowledgeable on the best local restaurants, bars and nightlife, scenic drives, historic spots and more; many of them are lesser known and therefore, secrets. All of this allows making planning for you more enjoyable for you and more memorable for those joining you. Allow is to be your Local Concierge!brbrThis house is not only perfect for bourbon fans, paddlers, and fishermen and women, but also for those wanting to enjoy Frankfort, the Kentucky State Capital. A short drive gets you to the Capital building, the Library and Archives, the Governors Mansion and most state offices. As well, located nearby is the Kentucky History Museum,, the Frankfort Museum, Fish and Wildlife's Salato Center, Rebecca Ruth Candies, and the Kentucky River. A great way to see much of this would be with our business, The Bourbon Boat aka Kentucky River Tours, who offers river history cruises and are considered one of the number one reviewed attractions in Frankfort. Of course we highly recommend. brbrLastly., the home is conveniently located near many of Kentucky's horse farms, as well as the Keeneland Race Track, only 20 minutes away. Downtown Lexington is 30 minutes away. The Ark Encounter is 60 minutes away, as well as downtown Louisville. brbrJust a mile from Jim Beam and right on the river, this airy little ‘preachers cabin’ has been converted into a 3- bedroom VRBO! It’s an open, airy floor plan and my favorite parts were the big hot shower and a big soft bed in a big open bedroom.. also the church-size parking lot. There’s an ‘Old Fashioned’ waiting to be made in the kitchen, enough privacy to play fetch with our dogs by the river, and it has a really ‘’safe’ feeling which was nice with all the kayaks on top of the truck. Just having a dog-walk I met a neighbor that owns the next-door church and another neighbor who was walking his dogs on the river and happy to chat. It’s a quiet, easy access launching point for your river excursion or Distillery tour.. feels rural but just 5-10 minutes from town stuff and the highway. Highly recommended.brClay Wright, Professional Whitewater Kayaker, Sparta TN

Centrally Located to Many Distilleries House on the Kentucky Bourbon Trail

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$138.75

Historic downtown guest suite with modern amenities located in the heart of the capital city. Within blocks of great dining, shopping, entertainment, and historic sites. A short distance to Buffalo Trace distillery, Keeneland racetrack and beautiful bluegrass horse country. Conveniently located 30 minutes from Lexington and 50 minutes from Louisville.brbrLocated in a fully renovated circa 1850s building, this guest suite has quality and modern finishes throughout while retaining historic charm. Ground floor unit with fully furnished living room, bedroom, bathroom, and kitchenette with mini refrigerator, microwave, and a single cup coffee maker.brbrPrivate Guest Suite with following amenities:br -living room with cable TV, couch, arm chair and desk/workstationbr-bedroom with queen size bed and armoirbr-kitchenette equipped with mini refrigerator, microwave, sink and Keurig coffee makerbr-free wireless internet throughoutbrbrDining:br-many restaurants within walking distance including Serafinis, Bourbon on Main, Goodwood Brewery, Mi Fiesta Mexican, Kentucky Coffeetree, Buddy's pizza, Gibbys, White Light Diner, Subway, Capital Cellars wine bar, Jim's Seafood, Main Street Diner, Poppy's Bakery, Mrs. B's Bakery. A fantastic ice cream parlor (Hoggy’s) is just two doors down. brbrAttractions:br-The Grand Theatrebr-Kentucky History Centerbr-Riverview Park with access to the Kentucky River and walking trail to Buffalo Trace Distillerybr-Orlando Brown House & Liberty Hall National Historic Landmarkbr-Canoe KY offering canoe & kayak rentalbr-Old State Capitol & grounds br-Daniel Boone's Gravebr-Rebecca Ruth Candy store & Factory tourbr-Fort Hill historic site & parkbr-Kentucky State Universitybr-Kentucky Military History museumbrbrWithin close driving distance:br-State Capitolbr-Governor's MansionbrbrRegional attractions: br-within 30 minutes of Kentucky Bourbon Trail stops - Woodford Reserve, Wild Turkey & Four Roses distilleries

Downtown Guest Suite on Saint Clair

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$608.42

Steeped in history, warmed with classic and comfy finishes, this Downtown Frankfort property has been beautifully restored by Castle & Key. Featuring 3 bedrooms, 2 bathrooms, views of the Kentucky River, & so much more!brbrThe Stone House is an extension of Castle & Key, where guests will enjoy considered finishes, bespoke Castle & Key chocolates and scents as well as curated imagery depicting the history of the Castle and its surrounds.brbrLocated directly on main street, we are walking distance to local restaurants, shops, State Capital, museums, and so much more. Oh, did we mention, you will have views of the Kentucky River!brbrGuests are easily able to access Kentucky's finest attractions and experience multiple aspects of this diverse state. Located in Central Kentucky guests are easy able to access historic and diverse cities such as Harrodsburg, Lexington, Louisville, Midway, Frankfort, and Versailles.brbrReady to welcome guests from around the world, all living spaces are available for guests to use, including our private courtyard.brbrSituated in the heart of Kentucky’s capital city, Frankfort and within Central Kentucky, a place famous for its bourbon and horses, guests will be charmed by this recently renovated historic home. No matter your reason for travel, this home offers all the modern-day amenities a guest could desire. brbrThoughtful in every detail, guests will experience the historic charm through the signature style of Castle & Key.brbrFirst Floor: brThe modest mainstreet side entry belies a grand welcome within the antique doors. Guests will spill into a luxurious sitting room ripe for relaxation and libation after a long day of Kentucky adventure. Beyond the sitting room is a beautiful library filled with antique books, Castle & Key memorabilia and historic photographs.brbrThe dining room comfortably seats 8 guests. Local chefs specializing in local cuisine and farm to table fare are available to cater upon request. brbrAdjacent to the dining room is an informal bar space with all the tools needed to craft a perfect cocktail for yourself or your guests. brbrThe kitchen is stocked with crockery and cutlery and a full sized refrigerator, oven, dishwasher and coffee maker. Fresh coffee beans will be stocked for each stay. brbrThe back living room features a Smart TV, sitting area, and a second dining table that overlooks the Kentucky River. This space is perfect for guests to play games, enjoy a movie, converse about their Kentucky adventures, or simply enjoy the company of others. brbrOur first floor also features a full bathroom and screened in porch. brbrbrSecond Floor:brA beautifully restored walnut staircase leads guests to the second floor. Two large bedrooms with king beds and one extra large room with a king bed and a daybed are dressed with fine linens, robes and exceptionally comfy beds. There is a full bathroom with a lovely original stained glass window at the very top of the stairs. brbrEach bedroom features a Smart TV. brbrWe invite you to join us to enjoy Kentucky’s hospitality at its best.brbrGuests are able to walk to many local attractions, but the best way to travel Central KY, is by personal vehicle.brbrWe are located on Main Street and located next to Bourbon on Main. Our antique home is full of charm and character. There is a possibility for noise being downtown. Our kitchen and courtyard do overlook the outdoor dining area of Bourbon on Main. Please note that as it is an antique home, it is not fully accessible for some guests. Please inquire if you have questions about accessibility. brbrWe do not supply parking.brPARKING: Guests are able to park along Main Street

This house is a 3 bedroom(s), 2 bathrooms, located in Frankfort, KY.

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$213.23

Welcome to our Hillside Hideout Home! Beautiful red-brick house to relax with the whole family!brbr-BOURBON TRAIL– HORSE RACING– MOTORCYCLE TRIPSbr-9 Miles North of Frankfortbr-3 Miles to nearest gas station & liquor storebr-10 Miles to Buffalo Trace Distillerybr-Country Setting with gorgeous scenic viewsbr-Hot Tub open year round!brbrFamily friendly & pet friendly! (Pet fee applies) We also offer covered parking to keep motorcycles out of the weather! Full backyard with playset, gas grill, firepit, and large patio for outdoor functions!

Hillside Hideout With Scenic Bluegrass Hot Tub Views!

Frankfort, Kentucky, United States

3

Bed

1

Bath

7

Sleeps

$262.0

Escape to the charm of Kentucky horse country at this beautifully restored historic retreat in the heart of Frankfort. This 3-bedroom, 2-bath home blends timeless character with modern comfort, offering the perfect getaway for bourbon lovers, wedding guests, and weekend travelers. Minutes from Castle & Key Distillery, bourbon trail, downtown Frankfort, and scenic countryside views. Relax, unwind, and experience authentic Kentucky hospitality in a one-of-a-kind setting.

This house is a 3 bedroom(s), 2 bathrooms, located in Frankfort, KY.

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$97.07

Keep it simple at this peaceful and centrally-located place. Only minutes to the distilleries, restaurants and shopping. 2 miles from the interstate. Quiet neighborhood directly across from Juniper Hills Golf Course and Waterpark.

Condo

Capital City Condo #10

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$2106.32

Welcome to Bourbon & Birdies, a breathtaking 9-bedroom, estate in the rolling countryside of Frankfort, Kentucky. Designed for those who crave both luxury and connection, this expansive retreat sleeps up to 22 guests and offers an unforgettable experience of relaxation, adventure, and treasured family moments.brbrSet on a private and peaceful property, Bourbon & Birdies is more than just a place to stay—it’s a destination. Here, you can start your mornings with coffee by the serene lake, spend your afternoons kayaking, golfing, or enjoying the pool, rejuvenate in the sauna or wind down with a soak in the hot tub under the stars.brbrThis estate is built for laughter-filled gatherings and meaningful connections, whether it’s a game of putt-putt, a round in the golf simulator, or a cozy movie night in the home theater. For those who love to cook, the gourmet kitchen is fully equipped for preparing delicious meals to share around the large dining table.brbrEscape the city buzz and embrace the beauty of Kentucky’s countryside. Whether you’re celebrating a special occasion, reconnecting with loved ones, or simply seeking a rejuvenating retreat, Bourbon & Birdies delivers the perfect balance of sophistication and fun—a place where every stay becomes a cherished memory.brbr The Space – Designed for Comfort & Connectionbrbr Main Floor – Where Elegance Meets ComfortbrThe main level welcomes you with a beautifully designed open-concept space featuring a gourmet kitchen, a spacious dining area, and a cozy yet sophisticated living room with plush seating—perfect for gathering and unwinding.brbr Gourmet Kitchen – Fully stocked with high-end appliances, cookware, and plenty of seating at the breakfast bar.br ️ Large Dining Table – Enjoy family meals or game nights with a table big enough for everyone.br Living Room – Relax on the comfy sofas and soak in the peaceful countryside views.brbrMain Floor Bedrooms:br Master Bedroom (Sleeps 2) – King Bed, luxurious en-suite bath, and serene countryside views.br 1st Floor Bedroom (Sleeps 2) – King Bed, conveniently located near the main living areas.brWait, there's more! 2 sleeper sofas in the main living area to accommodate more family and friends. The more, the merrier! brbr Upper Level – Cozy & Spacious Sleeping QuartersbrThe upstairs area features five well-appointed bedrooms, each offering a cozy retreat for rest and relaxation.brbr Upstairs Bedroom 1 (Sleeps 4) – Full-over-Full Bunk Bed, perfect for kids or group travelers.br Upstairs Bedroom 2 (Sleeps 2) – Queen Bed, a private and peaceful escape.br Upstairs Bedroom 3 (Sleeps 4) – Queen Bed + Twin-over-Twin Bunk Bed, great for families.br Upstairs Bedroom 4 (Sleeps 2) – Queen Bed, simple yet elegant.br Upstairs Bedroom 5 (Sleeps 4) – King Bed, offering an extra touch of comfort + Twin trundle bed perfect for extra guestsbr Downstairs Bedroom 6 (Sleeps 2) – King Bed, quiet and comfortable.br Downstairs Bedroom 7 (Sleeps 2) – King Bed, tucked away for extra privacy.brbr ️‍♂️ The Basement – The Ultimate Entertainment Hub brStep downstairs into the entertainment-packed basement, where fun and relaxation come together!brbr Private Bar – Stock up on your favorite drinks and enjoy cocktail nights with friends.br⛳ Golf Simulator – Practice your swing, rain or shine!br Home Theater – Cozy up for movie night with a big screen and plush seating.br Karaoke Corner – Sing your heart out with family and friends!br Ice Cream Corner: Childhood Joy on repeat All-You-Can-Eat Ice Cream Sandwichesbrbrbr Outdoor Oasis – Nature, Relaxation & AdventurebrStep outside to enjoy the true beauty of the Kentucky countryside with a range of outdoor activities!brbr Private Mini Lake & ‍♂️ Kayaks – Paddle out for a peaceful morning on the water.br⛳ Putt-Putt Course – Fun for all ages! Challenge your group to a round of mini-golf.br ‍♀️ Pool & Hot Tub – Soak up the sun or relax under the stars.br Sauna – A perfect way to unwind and rejuvenate.br ️ Gym & Yoga Room – Stay active during your stay.brbr✨ The Perfect Escape in Frankfort, KYbrLocated just outside Kentucky’s capital, Bourbon & Birdies is secluded yet accessible, offering the best of relaxation and adventure. Whether you're exploring the nearby bourbon distilleries, enjoying a family getaway, or celebrating a special occasion, this estate provides the space, luxury, and entertainment to make your stay unforgettable.brbr Book now and experience the best of Kentucky at Bourbon & Birdies! ✨brbrbrIMPORTANT INFORMATION:brA signed rental agreement is required before your stay. Failure to sign will result in cancellation of your booking.brNo Smoking Inside: $500 fine for violations brIntimate Parties are allowed, but different rates and rules apply. Please contact us in advance. brParking: Ample space available. brPet Policy: $25/day pet fee, max 2 pets.

Heated Pool, Hot Tub, Mini Golf, Theater-Sleeps 28

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$230.06

Kick back and relax in this. 2BR/1.5BA home in a quiet Frankfort neighborhood—close to Buffalo Trace, downtown, the Capitol, and local parks. Enjoy , fast Wi-Fi, smart TVs, a fully stocked kitchen, board games, and easy self check-in. The home features a fenced yard with patio, grill, and outdoor seatingbr The home has a shared entry; once inside, the space is completely private with its own separate entrance. Designed for families, business travelers, and bourbon explorers alike. The Property primary bedroom features a 75 inch smart TV super comfy bed and a half bath the second bedroom features a queen bed and a55 inch smart TV and super comfortable bed the living room features a pullout sofa sleeper a flat screen 75 inch smart TV and plenty of room for guest step inside the fully stocked kitchen with pots pans wine glasses coffee maker dishwasher and oven right off the kitchen you have your dedicated workspace with a desk with USB ports right outside the kitchen is a beautiful covered patio with Blackstone grill and a fully fenced in yard outdoor games are in the shed after an awesome relaxing time outside step back inside to the super nice bathroom with provided soap shampoo body wash hair dryer and towels just minutes from downtown all distilleries and plenty of fun family business activities to do

Bourbon trail - conveniently located

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$252.97

Miss Reba's Love is a charming house with beautiful antique furniture, hardwood floors, as well as, modern day touches that give it that warm Kentucky feel. The bedrooms are generous sizes with very comfortable beds. There is also an attached sunroom on the back of the house for your enjoyment. The spacious backyard is completely fenced in. For those of you who enjoy the outdoors we are also located near many parks, the KY River, and Elkhorn Creek which provide activities such as golfing, swimming, fishing, canoeing and hiking. Come stay where you feel welcomed and loved. Let this place show you what the heart of family is all about. We are located in a quiet neighborhood minutes away from town. Perfect location for Bourbon enthusiasts, state government visitors, traveling medical professionals, and horse lovers. Conveniently located on the Bourbon Trail near Buffalo Trace (5 mi) Castle and Key (10 mi) Woodford Reserve (12 mi) and Lovers Leap Vineyard (8 mi). Minutes away from the Capitol. Also located near Keeneland (24 mi) and Churchill Downs-Derby (54 mi). Miss Reba's Love is centrally located between Lexington and Louisville.

Miss Reba's Love is a charming house with a warm Kentucky feel.

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$199.23

Newly renovated 1 bedroom, 2 story loft in the Historic St. Claire Entertainment District of Frankfort Kentucky. Enjoy the best Kentucky has to offer with easy access to famous distilleries such as Buffalo Trace and Woodford Reserve and enjoy live thoroughbred racing at Keeneland Racetrack in nearby Lexington, KY.brThe spacebr2 story, 900 square foot apartment. The apartment is located on the second floor of the building. There is no elevator so you must be able to use stairs. Full kitchen, with a cozy living room and dining area and half-bath are downstairs. Upstairs opens up to a large bedroom with a laundry room off the closet and a full bath. Both the living room and bedroom are furnished with smart TV's and free wifi throughout the unit.brGuest accessbrGuests will be given the code to the building's exterior doors and a personalized code for entrance to the loft door during their stay. There are approximately 25 stair steps to reach the 2nd floor where the unit is located. Security cameras are located at the exterior entrances for guest safety.brOther things to notebrRules are simple. No pets, no parties and no smoking inside the building.

1 Bedroom KY Bourbon Trail Loft in Horse Country

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$664.58

Step into luxury, fun, and relaxation at this one-of-a-kind retreat just about 4 miles from Buffalo Trace! Designed for bourbon lovers and groups seeking an unforgettable getaway, this spacious 4 bedroom, 3.5 bathroom home blends upscale comfort with endless entertainment.brbrSLEEPING ARRANGEMENTSbr➤ Bedrooms located in the lower and second floor.br➤ Primary Bedroom: Features a luxurious king-sized bed, complete with premium bedding and plush pillows. The room offers a balcony with a view to a serene farm and backyard, perfect for a morning coffee!br➤ Second Bedroom: Features another King size bed! Also with premium bedding and plush pillows.br➤ Third Bedroom: Yes, another King size bed! Because everyone deserves a good night sleep!br➤ Fourth Bedroom: A delightfully decorated bedroom with TWO Queen size beds! With its own office space!brbrOur house boasts tastefully decorated interiors with a bourbon inspired items! The perfect space to gather, dine, and unwind in style.brbrWe have a fully stocked kitchen and we mean stocked! All the spices and basic cooking supplies to grill, cook or even bake a cake! It also has its very own espresso & cappuccino machine for your morning coffee with style!brbrAMENITIESbr➤ TWO hot tubs! Perfect so everyone has their own space and can relax in comfort!br➤ The spacious backyard with a firepit is perfect for stargazing or making s’mores.br➤ Free high-speed Wi-Fi and convenient onsite parking with EV chargerbr➤ Smart TV with Roku for your favorite streaming servicesbr➤ Dive into fun with our exclusive game room with a pool table, shuffleboard, foosball, giant Jenga, giant connect 4, and more!br➤ Four arcade games! Yes, and they're the fun ones!br➤ A Karaoke machine! So you can sing your heart out with friends and family!brbrPRIME LOCATIONbr➤ 4 miles to Buffalo Trace Distillery & the heart of the Bourbon Trail.br➤ 4 miles to Jim Beam distillerybr➤ 9 miles to Castle & Key distillerybr➤ 10 miles to Glenns Creek Distillingbr➤ 12 miles to Woodford Reserve Distillerybr➤ 15 miles to Whiskey Thief Distilling Co. Distillerybr➤ 25 miles to Four Roses Distillingbr➤ Just 1 hour from Churchill Downs for the Kentucky Derby!br➤ About 1 hour to Ark EncounterbrbrWhether you're sipping bourbon, singing your heart out in the game room, or soaking in the hot tub, this home is your ultimate Bourbon Trail retreat. Book your stay today!brbrIMPORTANTbrBefore you arrive you will be asked to complete guest verification through third-party provider Truvi. This is done to ensure we are keeping up-to-date with short-term rental regulations as well as providing both our guests and our properties with extra protection. Truvi will contact you via email and/or text to complete the verification. brbrYou will also be given the choice between paying a security deposit or a non-refundable damage waiver. Please complete this step prior to arriving at the property to enable a quick and easy check-in process.brbrGuest accessbrDuring your stay, you'll have complete access to the entire home, ensuring privacy and comfort.brbrThe garage and one storage closet in the primary room will be unavailable to you.brOther things to notebrHOUSE RULESbrTreat our home with respect and care for it as you would your own. No smoking or vaping, no drugs, and no unregistered guests. See our guidebook for more details on the house rules. We do not allow pets in this home. Only 5 cars are allowed in the driveway at any given time. Do not park in the street. Quiet hours are form 10pm to 7AM brbrHOT TUB USE WAIVER AND RELEASE OF LIABILITYbrbrBy booking and/or using the hot tub during your stay, you acknowledge and agree to the following:br 1. Assumption of Risk: I understand that the use of a hot tub involves inherent risks, including but not limited to slipping, drowning, heat-related illness, and exposure to bacteria or chemicals. I voluntarily assume all such risks.br 2. Health Precautions: I affirm that no one in my party will use the hot tub if they are pregnant, have a heart condition, skin condition, or other health concerns unless cleared by a physician.br 3. Supervision Required: Children under 18 must be supervised by an adult at all times while using the hot tub. No diving or horseplay is permitted.br 4. No Alcohol or Glassware: I agree not to use the hot tub while intoxicated or to bring glass containers into the hot tub area.br 5. Waiver and Release: I, for myself and all members of my party, release and hold harmless the property owner, host, and their agents from any and all claims, injuries, or damages arising from the use of the hot tub, including but not limited to personal injury, illness, or death.br 6. Responsibility for Damage: I understand that I may be held financially responsible for any damage caused to the hot tub due to misuse or failure to follow these rules.brbrBy proceeding with this booking, I acknowledge that I have read, understood, and agreed to this Hot Tub Use Waiver.brbrCHECK-IN/CHECK-OUT DETAILSbrEasy self-check-in with a digital smart lock. Check in after 4 PM and check out by 10 AM. General checkout procedures are to lock the doors, close the windows, leave dishes clean or at least in the dishwasher, and leave used beds undone and used towels in the floor. Generally tidy up the place and leave it the way you found it. Nothing too complex :)brbrWhile you're here to enjoy the countryside vibes, we also want to make you aware of the local wildlife that calls this area home. We've seen birds, mice, spiders, skunks and other critters at the property. Since we are located in the countryside, there are occasionally some insects that can get inside the house if the doors or windows are left open.

2 Hot Tubs, Firepit, Gameroom, 4mi to Buffalo Trace

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$358.41

Welcome to Whiskey Woods, your secluded retreat nestled in the scenic neighborhood of Deerwood Estates in Frankfort, Kentucky! Situated on a sprawling 3.6-acre wooded property, this spacious and tastefully renovated 3-bedroom, 2-bathroom home offers 1344 square feet of modern comfort and style.brbrStep inside to discover a bright and inviting living space, thoughtfully furnished with contemporary decor and cozy seating areas. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating the perfect space for entertaining family and friends.brbrThe fully equipped kitchen boasts sleek countertops, stainless steel appliances, and all the essentials you need to prepare delicious meals during your stay. Enjoy your culinary creations in the adjacent dining area, or step outside to the private patio for al fresco dining surrounded by lush greenery.brbrExplore the expansive wooded property and discover a tranquil oasis complete with a grill and fire pit, perfect for gathering around with loved ones under the starry Kentucky sky.brbrRetreat to one of the three beautifully appointed bedrooms, each offering plush bedding and ample storage space for your belongings. The master bedroom, fittingly named the Whiskey Suite, features a luxurious king-sized bed and an en-suite bathroom for added privacy and convenience, while the other two bedrooms are furnished with comfortable queen-sized beds.brbrOther amenities of Whiskey Woods include high-speed Wi-Fi, a washer and dryer for your laundry needs, and off-street parking for your vehicles. We also do have outdoor cameras monitoring the exterior of the property, so you rest-assured knowing the property is safe and secure. brbrLocated just minutes from downtown Frankfort, you’ll have easy access to local attractions such as the Capitol building, museums, and scenic parks. Whether you’re here for business or pleasure, Whiskey Woods provides the perfect blend of comfort and convenience for your Kentucky adventures.brbrBook your stay at Whiskey Woods today and experience the best of Frankfort living amidst nature’s beauty!br

Secluded Retreat in Scenic Frankfort w/ Hot Tub: Whiskey Woods - Book Now!

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$290.62

Extra-large two-bedroom apartment with dedicated, private outdoor space in the center of historic downtown Frankfort, Kentucky. Within close proximity to some of Kentucky's best distilleries and easy walking distance to great restaurants, shops, bars and breweries. The perfect home base to explore everything the Bluegrass region has to offer!

Duvall's Downtown Guest Retreat

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$168.07

CARRIAGE ON CAPITALbrWelcome summer at a chic Parisian-style hideaway in Historic Frankfort, where charm and comfort meet in every detail. Just minutes from 13 iconic distilleries and the KY Capitol, this cozy retreat is perfectly placed for bourbon tastings, local history, and leisurely city strolls. Inside, enjoy fast Wi-Fi, a smart TV, full kitchen, private entry, and free parking. Rest deeply in a plush queen bed, then sip coffee or wine on the bistro deck as warm summer days fade into relaxed, perfect nights.brbrTHE SPACEbr- Recently renovated, this carriage house embraces all the modern comforts to ensure a stay filled with moments of pure comfort and contentment. brbrExperience the essence of hygge in our space. Nestled within, you'll find a plush Queen size bed, an modern bathroom, and a kitchen fully equipped for your needs. Skylights gently filter in natural light, creating a warm and inviting atmosphere that envelops you.brbrFor those practical necessities, we've taken care of it all. From laundry essentials to bedding supplies, we've thoughtfully curated every detail to ensure your stay is as comfortable as can be. And to top it all off, a delightful goodie bag awaits your arrival, a token of our appreciation for choosing to make our space your home away from home.brbrSo pack your bags, leave your worries behind, and come experience this recently revitalized getaway. All you need to bring are your personal essentials; we'll take care of the rest.brbrGUEST ACCESSbr-Imagine the seamless entry provided by the cutting-edge smart lock, beckoning you to enter your exclusive retreat in Frankfort. The entirety of the Carriage is dedicated to your comfort, creating a snug haven that's yours for your stay.brbr-But that's not all—there's also a charming bistro table waiting for you on the deck, perfect for relishing the outdoors. Come savor the feeling of home away from home and bask in the delightful ambiance we've prepared just for you!brbrTHINGS TO NOTE:br- Make it a surprise and enhance your arrival and stay, arranged items can be placed in your space.br-Just a heads up, a mini stair-climbing adventure awaits you before you reach your cozy haven! br-There’s a plethora of curbside parking right by the property – parking galore!br-We have additional listings that could also cater to your accommodation preferences!brbrTHE NEIGHBORHOOD:brQuiet historic residential area in Downtown Frankfort. Our property is nestled at the heart of Kentucky; Frankfort offers an easy commute to three other vibrant cities: a mere 35-minute drive to | Lexington, just 50 minutes to | Louisville, and an adventure-packed 1 hour and 24 minutes to the captivating | Cincinnati.brbrThe neighbor is safe & ideal for running, walking, and leisurely strolls, offering a pleasant path leading to the Capitol grounds and the Governor's Mansion!brbrGETTING AROUND:brGuests can walk to downtown Frankfort and the Kentucky State Capitol, however the best means of transportation is a personal vehicle. Easy drives to the following 13 Bourbon Distilleries:brbr1. Buffalo Trace Distillery in Frankfort, Kybr2. Castle & Key Distillery in Frankfort, Kybr3. James Pepper Distillery in Lexington, Kybr4. Bluegrass Distillery in Lexington, Kybr5. Barrel House Distillery in Lexington, Kybr6. RD One Distillery Tasting Room in Lexington, Kybr7. Lexington Brewery & Distillery in Lexington, Kybr8. Whiskey Thief Distillery in Graefenburg, Kybr9. Woodford Reserve Distillery in Versailles, Kybr10. Wild Turkey Distillery in Lawrenceburg, Kybr11. Four Roses Distillery in Lawrenceburg, Kybr12. Jeptha Creed Distillery in Shelbyville, Kybr13. Bulleit Distillery in Shelbyville, Ky

The Carriage - Quaint Haven 6 mins. to Buffalo Trace

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$239.99

LOFT ON CAPITALbrStep into spring at The Loft, your cozy, hygge-inspired escape just minutes from downtown Frankfort. Wander the KY Capitol, enjoy the most perfect house vibes, and explore nearby Horse Country in the perfect summer weather. Curl up in your sunlit second-floor hideaway with a plush bed, comfy sofa, and thoughtful modern touches. With parking at the door and a cool, peaceful vibe, The Loft invites you to slow down, savor the season, and relish a getaway on the Bourbon Trail.brbrTHE SPACE:br-Experience the essence of hygge in our beautifully restored historic space, where character, comfort, and charm blend seamlessly. This inviting space guarantees total relaxation with its panoramic kitchen view, the coziest queen bed, a soothing clawfoot tub, as well a separate standalone shower.brbr-Sunlight bathes every corner of the space, creating a warm and inviting atmosphere, while smart TVs in both the living room and bedroom provide access to your favorite streaming platforms. As evening descends, a record player sets the stage for a cozy and unhurried night of hygge “coziness”brbr-Spacious and well-equipped kitchen, guests can craft culinary delights in a private and inviting sanctuary.brbrFor those practical necessities, we've taken care of it all. From laundry essentials to bedding supplies, we've thoughtfully curated every detail to ensure your stay is as comfortable as can be. And to top it all off, a delightful goodie bag awaits your arrival, a token of our appreciation for choosing to make our space your home away from home.brbrSo pack your bags, leave your worries behind, and come experience this recently revitalized getaway. All you need to bring are your personal essentials; we'll take care of the rest.brbrGUEST ACCESS:br-Picture the effortless access granted by the state-of-the-art smart lock, inviting you to step into your very own Frankfort haven. The entire Loft unfurls as your personal cozy spot, ready to be enjoyed and savored. brbr-And oh, the delightful outdoor deck – a chill space where you can unwind and bask in the moment. Immerse yourself completely, feeling an unparalleled sense of belonging and the limitless possibilities that comes with being in your home away from home!brbrTHINGS TO NOTE:br-Make it a surprise and enhance your arrival and stay, arranged items can be placed in your space. br-Just a heads up, a mini stair-climbing adventure awaits you before you reach your cozy haven! br-There’s a plethora of curbside parking right by the property – parking galore!br-We have additional listings that could also cater to your accommodation preferences!brbrTHE NEIGHBORHOOD:brQuiet historic residential area in Downtown Frankfort. Our property is nestled at the heart of Kentucky; Frankfort offers an easy commute to three other vibrant cities: a mere 35-minute drive to *Lexington, just 50 minutes to *Louisville, and an adventure-packed 1 hour and 24 minutes to the captivating *Cincinnati.brbrThe neighbor is safe & ideal for running, walking, and leisurely strolls, offering a pleasant path leading to the Capitol grounds and the Governor's Mansion!brbrGETTING AROUND:brGuests can walk to downtown Frankfort and the Kentucky State Capitol, however the best means of transportation is a personal vehicle. Easy drives to the following 13 Bourbon Distilleries:brbr1. Buffalo Trace Distillery in Frankfort, Kybr2. Castle & Key Distillery in Frankfort, Kybr3. James Pepper Distillery in Lexington, Kybr4. Bluegrass Distillery in Lexington, Kybr5. Barrel House Distillery in Lexington, Kybr6. RD One Distillery Tasting Room in Lexington, Kybr7. Lexington Brewery & Distillery in Lexington, Kybr8. Whiskey Thief Distillery in Graefenburg, Kybr9. Woodford Reserve Distillery in Versailles, Kybr10. Wild Turkey Distillery in Lawrenceburg, Kybr11. Four Roses Distillery in Lawrenceburg, Kybr12. Jeptha Creed Distillery in Shelbyville, Kybr13. Bulleit Distillery in Shelbyville, Ky

The Loft - Cozy Retreat in Historic Downtown

Frankfort, Kentucky, United States

Bed

Bath

Sleeps

$217.39