Home Vacation Rentals By Owner In Midway, KY

Showing 17 Of 17 Vacation Rentals
Slider Thumb
Exceptional(52)

$551.2

/ Nightly
Private Vacation Home

Family-friendly newly built house in the heart of Kentucky's Horse Country

Midway, Kentucky, United States

Nestled in the heart of Kentuckys Bluegrass region, The Dew Drop In, newly constructed in 2018, is located on Saxony Farm, a working Thoroughbred horse farm, family-owned and operated for over 50 years. More than just a place to rest your head, guests will experience a home-away-from-home location, & enjoy the peace and quiet of farm life, all within striking distance of downtown Lexington, KY s Bourbon Trail, locally-owned restaurants, shops and numerous family-friendly activities.br
Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
Slider Thumb
Exceptional(182)

$299.03

/ Nightly
Private Vacation Home

Bourbon Trail, Horse Park & Farms, Keeneland, Vineyard & Winery

Midway, Kentucky, United States

The Cottage is an old family farm house that's been totally renovated and offers all new amenities. You also have the perfect front porch view of picturesque Equus Run Vineyards, located just across the road, and access to South Elkhorn Creek. Have a cup of coffee on the front porch and enjoy the sunrise over the vineyard.brbrIt's in heart of horse country, but close to:brKentucky Bourbon TrailbrKentucky Horse ParkbrKeeneland Race TrackbrEquus Run Vineyard & WinerybrSaddlestone DistillerybrOld Friends Thoroughbred Retirement FarmbrHistoric MidwaybrLexington, Georgetown, Frankfort and Louisville. brbrExcellent dining choices are close by in Midway, Lexington, Georgetown and Frankfort. brbrThe cottage is easily accessible from I-64 via two exits and sits on 15 acres on a beautiful country road nestled in the midst of thoroughbred horse farms. Guests have access to the entire house. Feel free to walk throughout the 15 acres, read a book on the front porch, fish down at the South Elkhorn Creek, put your kayak in the creek, or relax on the back covered patio or gazebo. brbrEach of the three bedrooms has a queen bed and private full bath. Bed linens, towels, basic toiletries and hair dryers are provided. The kitchen is fully functional so you can enjoy cooking tasty creations or just opting for a cup of coffee in the morning. A full laundry room is off the kitchen area. The living and dining area is a wonderful co-mingled space with views out to the vineyard. The house is comfortable, cozy, and updated.brbrFor Kentucky Bourbon Trail Explorers--brThis is the perfect spot to stay if you're working your way through the Kentucky Bourbon Trail. Five of the distilleries are less than 25 miles away; the furthest is 75 miles away. Several craft distilleries, breweries and wineries are also nearby. In just a few short day trips you will be able to take in the trail and hit some other spots as well!brbrFor Horse Lovers and Racing Fans--brSaddlestone's neighbors are thoroughbred farms including Glencrest, Audubon, and Margaux farms. Zenyatta, a Breeder's Cup favorite, resides at Lane's End Farm, and triple crown winner American Pharaoh is at Coolmore's Ashford Stud--both in Versailles, which is a short 15 minute drive away. Old Friends Thoroughbred Retirement Farm is 5 minutes away and Keeneland and the Kentucky Horse Park are each about a 15 minute drive. brbrFor Foodies and Gastronomes--brIt's a definite--you will not go hungry! Lexington, Midway and Georgetown have an amazing array of non-chain, independent restaurants. There's farm-to-table, southern infused, time-honored recipes to the latest culinary trends, the restaurant scene is sure to impress. brbrFor History Lovers--brYou'll want to visit Ashland, the estate of Kentucky's greatest statesman, Henry Clay, and the Mary Todd Lincoln home. Both are located in Lexington. Dr. Thomas Hunt Morgan, the father of modern day genetics, was born in Lexington and was the first Kentuckian to win a Nobel Prize. The Hunt-Morgan House, located in beautiful, historic Gratz Park, is also open for tours. On the Frankfort side, you can visit Daniel Boone's grave in the Frankfort Cemetery or take in a tour of Rebecca Hunt Candy. Shakertown at Pleasant Hill is a wonderful place to hike, bike, and dine. Take in some amazing architecture and stay for a delicious meal at the Trustees Table.brbrFor Civil War Buffs--brCamp Nelson was established as a supply depot and hospital during the Civil War for the U.S. Army and became a large recruitment and training center for African American soldiers (USCTs), and a refugee camp for their wives and children. Thousands of enslaved people escaped to this site with the hope of securing freedom and ultimately controlling their futures by aiding in the destruction of slavery.brbrPerryville Battlefield became the site of the most destructive Civil War battle in the state which left more than 7,600 killed, wounded or missing. The Perryville Battlefield park museum tells of the battle that was the South’s last serious attempt to gain possession of Kentucky.brbrBirthplaces of Abraham Lincoln and Jefferson Davis. Both presidents during the Civil War were born in Kentucky. Lincoln in Hodgenville and Davis in Fairview.brbrSo, relax and enjoy the perfect home base for touring the Bourbon Trail, visiting Keeneland, taking in historical sites or enjoying a glass of wine on the front porch swing. This is the perfect country retreat while being close to everything!
Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(1)

$324.3

/ Nightly
Private Vacation Home

Fire Pit + Yard: Peaceful Bluegrass Escape!

Midway, Kentucky, United States

10 Mi to Kentucky Horse Park | Pet Friendly w/ Fee | Close to Bourbon Trail DistilleriesbrbrExperience the heart of horse country at this inviting Midway vacation rental! Whether you're here to see races at Keeneland, visit loved ones at UK, or explore nearby farms, this property offers a quiet, scenic place to recharge. With 3 bedrooms, 1 bath, a full kitchen, and a spacious yard, it’s an ideal, relaxed spot for groups seeking a genuine Kentucky countryside getaway. Saddle up and book today!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 full bedbr- Bedroom 3: 1 full bedbrbrHOME FEATURESbr- Spacious deck & yardbr- Fire pit (wood not provided)br- Smart TV, DVD playerbr- Board gamesbr- Shower/bathtub combobrbrKITCHENbr- Stove, oven, dishwasher, microwavebr- Drip coffee maker, blender, toasterbr- Cooking basics, spices, dishware & flatwarebr- Custom cabinets, island dining area, high chairbr- Trash bags/paper towelsbrbrGENERALbr- Central heating & A/Cbr- Washer & dryer, laundry detergent, iron/boardbr- Linens/towels, complimentary toiletries, hair dryerbr- Free WiFibrbrFAQbr- 4 exterior security cameras (facing out)br- Pet fee (paid pre-trip)brbrACCESSIBILITYbr- Single-story home, step-free accessbrbrPARKINGbr- Driveway (4 vehicles)brbr-- THE LOCATION --brbr- Serene rural setting surrounded by world-class thoroughbred horse farmsbr- 1 mile to Weisenberger Mill & The Vintage Barn At Merefieldbr- 10 miles to Kentucky Horse Park & Keenelandbr- 7 miles to Masterson Station Parkbr- 11 miles to Lexington attractions: McConnell Springs Park, Lexington Children’s Museum, The Arboretum, State Botanical Garden of Kentucky, University of Kentuckybr- 12-15 miles to Woodford Reserve Distillery, Buffalo Trace Distillery & Castle & Key Distillerybr- 11 miles to Blue Grass Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $50 fee (+ fees & taxes)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story home offers step-free accessbr- Your safety matters. This property features 4 exterior security cameras located on each side of the house facing the yard, driveway, side of the house, back porch, shed, and HVAC units. The cameras do not look into any interior spaces. All cameras record video and audio when activated by motion
Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(21)

$1451.5

/ Nightly
Private Vacation Home

HOLIDAY HOUSE - Kentucky Bluegrass Home on Champion Thoroughbred Farm

Midway, Kentucky, United States

Holiday House of Midway, Kentucky is a neoclassical southern estate home perched majestically atop a hill overlooking Elkhorn Creek and bordered on the remaining three sides by an esteemed thoroughbred farm. brbrNotable features of the 2.5-acre property include the 5-bedroom home with two screened porches, wood burning fireplace, wine cellar, dry sauna, steam shower, and home gym; brick paved terrace; stone tiled pool deck with gas-heated swimming pool, in-ground brick fire-pit with seating; grassy lawns and mature trees, including the prized 300+ year old Cinquapin Oak that pre-dates the founding of Lexington. The property is bordered by an impressive Kentucky stone fence and from every window, porch and terrace, you’ll be greeted with views of Margaux Farm’s horse paddocks, where thoroughbreds in training or rehab spend their days grazing and playing. The cheerful sound of whinnying and neighing horses outside makes one want to shut off the phone and music and just enjoy authentic country living!brbrHOUSE DETAILS: From the front entry, steps lead up to the main floor and down to the lower level. The main floor includes at the front, our “Sunset Room”, a sitting room with west views down to the creek, and at the back of the house, the modern open kitchen, family room and dining room with sliding doors to a screened porch and french doors out to the pool area. In between is a home office, enclosed by french doors and open to the sunset room. Down the hall, there are three bedrooms - a king suite (king bed, ensuite bath with dual vanities, large soaking tub and steam shower), queen suite (queen bed, ensuite bath with tub/shower combo), and a large guest bedroom (two twin beds plus a day bed and trundle, sleeps up to 4). In addition to the two ensuite bathrooms, there is a full bath off the hallway that serves the guest bedroom and as a powder room. Downstairs, two additional guest bedrooms, one with a king and one with a queen bed, share a common bathroom with a tub/shower combo. Also downstairs is the TV room with a leather power recliner sectional, 65” TV, and Bourbon tasting setup; a small home gym with Cybex Arc trainer, free weights, bands and mats; wine cellar and dry sauna; and a laundry room with large washer and dryer. brbrLOCATION: The property is set in the perfect location for enjoying all the best of the inner-Bluegrass region. Downtown Lexington is a straight shot down Leestown Road, about 20 minutes, and notable attractions such as Keeneland Race Track, the Kentucky Horse Park, Buffalo Trace Distillery and Woodford Reserve Distillery are within a 20-30 minute drive down the breathtakingly beautiful Kentucky scenic byways. Historic and charming downtown Midway is a 5-minute drive and Equus Run Vineyards is just a mile down Moore’s Mill Road - a horse farm and winery, how’s that for neighbors Elkhorn Creek, which forms the west border of the property, is a popular local destination for small mouth bass fishing, fly fishing and whitewater rafting and you will see people park at the end of the driveway to launch their rafts.brbrHoliday House is truly a special place and we look forward to welcoming groups of couples and mature families, for whom the property is ideally setup to accommodate. brbrIMPORTANT NOTES: br- The pool is open seasonally from Memorial Day-Labor Day. If you want to heat the pool, gas usage for the pool heater will be charged separately from your booking costs. br- There is a security camera that surveils the driveway/parking area that picks up audio. There are no cameras inside the residence or outdoor living areas.
Bed 5

Bed

Bath 4

Bath

Sleep 8

Sleeps
Slider Thumb

$139.52

/ Nightly
Private Vacation Home

Entire home located in Midway, ky.

Midway, Kentucky, United States

Discover downtown Midway, KY's allure in this 3-bed, 2-bath Airbnb. Modern amenities blend with rustic charm, offering cozy living spaces, a fully equipped kitchen, and a tranquil backyard retreat. Located near horse farms and within walking distance of downtown Midway, it's an ideal base for exploring the Bluegrass Region. Enjoy everything Midway has to offer when you stay with us. This is a minimum 30 day accommodation.
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(72)

$296.36

/ Nightly
Private Vacation Home

Bit and Bourbon

Midway, Kentucky, United States

Located in the heart of historic downtown Midway, this private, tucked away home has been fully renovated. It features two bedrooms with king sized beds, two spa-like bathrooms, a full sized kitchen, quaint dining room, and living room. There is a private deck to enjoy a cup of coffee in the morning or a glass of wine or bourbon in the evening. This home is just a walk around the corner from downtown’s shops and award winning restaurants. Within minutes from Keeneland, the Kentucky Horse Park, Versailles, Frankfort, and Lexington. This makes it ideal to tour the bourbon trail as well. An added bonus is an electric charging station in the parking lot!
Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
Slider Thumb
Exceptional(131)

$296.15

/ Nightly
Private Vacation Home

Charming Cottage Conveniently Located In The Heart Of Horse And Bourbon Country

Midway, Kentucky, United States

This newly renovated and furnished home is only 3 1/2 blocks from historic Midway's downtown shops and restaurants. Clean, allergy & scent-free space. Hardwood & tile floors throughout. There are two bedrooms upstairs, one w/ a Queen and twin, one w/ two twin that can convert to a King and the Master Bedroom downstairs has a Queen bed. It can sleep seven. There are three flat screen TV's, one in the Living room and one in each bedroom upstairs w/HBO & SEC channels.Wifi Internet Access is provided. The Kitchen/Breakfast room is spacious w/ microwave, coffeemaker & toaster oven. There is equestrian and local art throughout. The porch is charming, relaxing and private with a ceiling fan and infrared grill. On site off street parking with a two car garage. There is a Bakery two doors down and a playground behind. The cottage is located in the heart of Thoroughbred and Bourbon country. Midway is off of I-64, just 20 minutes from Lexington and and hour from Louisville- you can hit every destination on your vacation easily.
Bed 3

Bed

Bath 2

Bath

Sleep 7

Sleeps
Slider Thumb
Exceptional(16)

$123.45

/ Nightly
Apartment

Modern Remodeled Downtown Midway Studio

Midway, Kentucky, United States

One BR studio apartment in heart of charming, downtown Midway. Historic building w/ NEW, complete remodel done in 2020. Full Kitchen w/ stove, microwave, dishwasher, coffee maker. Washer/Dryer. Private bath w/ tile shower. Exposed, original brick wall. Restored hardwood floors. WiFi. TV with Hulu, Prime, and Netflix. Walk-thru closet. Professionally cleaned/sanitized after each guest.
Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
Slider Thumb
Exceptional(39)

$248.04

/ Nightly
Cabin

Cozy cabin in the heart of horse country

Midway, Kentucky, United States

1800 sq ft cabin less than 3 minutes from downtown historic midway. Located centrally to all the horse farms and bourbon distilleries located in Lexington Frankfort Versailles and Midway. Sits on an acre of land and backs up to a 300 acre farm.
Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
Slider Thumb
Exceptional(3)

$597.14

/ Nightly
Private Vacation Home

Charming 3-bedroom house in Midway with screened in porch and salt water pool!

Midway, Kentucky, United States

Get ready to relax in this charming 3-bedroom house in Midway. This gorgeous property features a first floor master with king bed and walk in shower, and 2 additional bedrooms upstairs-one with a queen sized bed, and the second with a king sized bed plus a semi private alcove with two twin beds. With three bathrooms equipped with hair dryers and showers, guests can unwind in comfort. Our second living room has a pull out couch for extra sleeping space; this room can be completely closed off to act as a 4th bedroom. Relax with a cool drink on our spacious screened in porch overlooking the garden and salt water pool or take a short walk to Main St where you will find several great restaurants, bars, and antique shops. We're happy to answer any questions you may have about the home or the area!
Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
Slider Thumb
Exceptional(51)

$148.2

/ Nightly
Private Vacation Home

Railway Guest House in Charming Midway KY Horse Park,Bourbon Trail,Keeneland.

Midway, Kentucky, United States

This unique, early 1800’s historic house sits 50 FEET from the railroad. The train blows by 3x during the day, tooting & whistling away & once or twice at night. It is the second oldest residence built in Midway. The plot of land where the house sits was one of the initial purchases from the railroad company which was one the first towns in KY to build a Railroad Town. GUESTS NEED TO CONFIRM THEY CAN HANDLE THE ORIGINAL OLD STEEP & NARROW STAIRCASE BEFORE BOOKING ACCEPTED. brGuests will enjoy their private, bright & cozy upstairs with 2 nicely sized bedrooms with plenty of closet space. The bathroom in between the bedrooms & breakfast nook is very small, but clean & efficient. There is a mini fridge, coffee & tea station. Ice bucket @ 5:00 pm each night is available upon request. Entrance & exit is through the front door & through the one-room art gallery which is closed off from the rest of the house. 9 ORIGINAL VERY STEEP & NARROW STAIRS leads to the cheery upstairs accommodations. STAIRS ARE NOT FOR PEOPLE WITH MOBILITY ISSUES. BIG, HEAVY SUITCASES ALSO WILL POSE A PROBLEM IF YOU ARE NOT UP FOR WRANGLING THEM UP THE 9 STAIR CLIMB. GUESTS MUST ACKNOWLEDGE THEY HAVE SEEN/READ RE. STAIRS BEFORE BOOKING IS ACCEPTED Please see pictures :)brAmple off street parking is available. If you are bicycle-touring/racing, garage arrangements in back can be be made for bicycles. Off street horse trailer parking can also be arranged.brEllen, the host, lives in the back part of the house which is closed off from the art gallery room & upstairs. The house is located on the residential side of Main St. (aka Railroad St.) & is 1/2 block away from restaurants & shops where you will also find Ellen’s Art Gallery & Gift Shop THROW ME A CARROT. She can be reached anytime if needed on her cell phone (preferably by text) during your stay. Guests receive 15% discount at THROW ME A CARROT :)
Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
Slider Thumb

$384.37

/ Nightly
Private Vacation Home

Family Fun Retreat - Pickleball, 9 Hole Mini Golf, Hot Tub + Fire Pit + Jukebox

Midway, Kentucky, United States

Welcome to this adorable house in Midway.brbr- Pickleball Court (DIY)br- Gazebo with Hot Tubbr- Vintage Jukeboxbr- Fire Pit with Adirondack Chairsbr-9 Hole Mini Putt Putt Golf CoursebrbrAs soon as you step inside this beautiful home, you’re greeted by a warm, comfortable living area with peaceful views of Kentucky horse country. Nestled near the bourbon trail, it’s the perfect place to relax and enjoy everything the area has to offer.brbrThe full kitchen leads into the dining area, offering a place to cook and enjoy tasty delicacies before unwinding in the entertaining living room with the vintage jukebox, setting the scene for unforgettable evenings. Natural sunlight bursts through large windows, making the home shine bright during the day, touching the hardwood floors, stylish details, and carefully chosen furniture, and enhancing the pleasant setting.brbrRecharge in the three comfortable bedrooms, which boast high-end comforts that allow you to rest after an exciting day of sightseeing and outdoor activities.brbrStep outside into your private countryside retreat, where rolling hills and nearby horse farms create a serene backdrop. Challenge your companions to a friendly match on the DIY pickleball court, then unwind in the gazebo-covered hot tub, soaking in the tranquil views. As evening falls, gather around the fire pit to roast marshmallows and share stories under the starry Kentucky sky.brbrWhen you've had enough of the great outdoors, retreat to the basement family room featuring a one-of-a-kind, DIY 9-hole putt-putt course whose low ceilings and ductwork add to the challenge and entertainment!brbrThere's so much to do in this stunning house. We look forward to you experiencing its complete coziness and comfort.brbrLiving Room-brYou will feel right at home! Sink into the comfy sofa, watch your favorite show, play your favorite tunes on the unique jukebox, or plan your upcoming Kentucky adventures.brbr- Comfortable L-Shaped Leather Sofabr- Smart TVbr- Vintage Jukeboxbr- Decorative Fireplacebr- Chic Sofa ChairsbrbrBASEMENT GAME/FAMILY SPACE-brCome to the basement to discover numerous relaxing and entertaining amenities. Be careful, though. You'll quickly lose track of time in this fun space!brbr- DIY 9-hole Duck Duct Putt-Putt Golf Coursebr- Smart TVbr- Cozy SofabrbrKITCHEN & DINING-brThis fully equipped kitchen boasts modern appliances, making it easy to whip up anything from delicious breakfasts to gourmet dinners. brbr- Microwavebr- Stove br- Ovenbr- Coffee Maker (Coffee, Decaf, Creamer, Sugar)br- Refrigerator/Freezerbr- Platesbr- Glassesbr- Silverwarebr- Pots & PansbrbrCatch up with your loved ones in the lavish backyard while the food is prepared. When done, gather at the dining table and savor a delicious meal in an inviting atmosphere. brbr- Dining Table with Seating for 6brbrSLEEPING ARRANGEMENTS – 3 BEDROOMSbrAfter an exciting day of exploring thrilling attractions and scenic landmarks, you will look to rest for an equally entertaining tomorrow. Once you are ready to relax, please make your way to these comfortable bedrooms.brbrMaster Bedroom: King-Size BedbrBedroom 2: Queen-Size BedbrBedroom 3: Queen-Size BedbrbrAll bedrooms share a similar set of amenities.brbr- Premium Mattresses, Linens, Sheets, and Pillowsbr- Closets with Hangers and Shelvesbr- Night Stands with Reading LampsbrbrBATHROOMSbrThe accommodating home boasts a spa-like full bathroom stocked with pampering towels and necessities to ensure a carefree stay. brbr- Soaking Bathtub with a Showerbr- Mirrorbr- Toiletbr- Towelsbr- Hair Dryerbr- Essential ToiletriesbrbrBACKYARDbrA stunning haven wouldn’t be complete without a private outdoor space to soak in the serenity and beauty of nature. Step into the backyard to unwind in the hot tub, gather around the fire pit for relaxed evenings, and take in the peaceful surroundings of Kentucky’s scenic landscape.brbrYou’ll also find a DIY pickleball court! Nothing fancy or professional, but perfect for a friendly match, a little competition, and plenty of laughs.brbr- Pickleball Court (DIY)br- Gazebo with a Luxurious Hot Tubbr- Fire Pit with Adirondack ChairsbrbrFind your happiness in this attractive retreat. It offers a place to escape the hustle and bustle of everyday life, cuddle on the sofa, watch a movie, unwind in the hot tub, and explore the exciting Kentucky bourbon trail.brbrNO SMOKING INSIDEbrPlease refrain from smoking inside the home! Any smoking evidence will result in a $350 fee for odor removal and furniture cleaning.brbrNO PARTIES/EVENTSbrWe kindly ask you to treat our home as your own to preserve its pristine condition for future guests and your return visits.brbrNO LOCAL RESERVATIONSbrReservations from guests within their city of residence are not allowed. Please contact us if you are booking within your city.brbrAll guests are required to sign a rental agreement after booking.brbrThank you very much for your understanding.brIf you have any questions, don’t hesitate to reach out. Happy travels!
Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(4)

$400.24

/ Nightly
Private Vacation Home

Welcome to FarRhode Stable! A new, charming, 3 bedroom, 2-bathroom luxury condo perched above a beautiful barn. You will feel like a true Kentuckian with the gorgeous views of horses, cattle, donkeys, & even ducks! Book now for a perfect stay!

Midway, Kentucky, United States

Welcome to FarRhode Stable! A new, charming, 3 bedroom, 2-bathroom luxury condo perched above a beautiful barn. You will feel like a true Kentuckian with the gorgeous views of horses, cattle, donkeys, & even ducks! Here you will find 2 king beds, 2 twin beds, 2 full bathrooms with walk in showers, a fully stocked kitchen to prepare your favorite meals, & a stunning patio with a grill. Don't worry, your horses have a stall to stay in too! Book this brand new condo now, you will not regret it!! brbrHosts are not on site, but available 24/7 through your booking platform. brbrNestled in the heart of Kentucky Horse Country, this luxury condo offers the perfect blend of peaceful farm life and convenient access to the region’s best attractions. Wake up to views of horses, donkeys, and ducks, then explore world-class equestrian destinations and charming towns just minutes away.brbrKentucky Horse Park – 22 miles / 25 minutesbrbrKeeneland Racecourse – 17 miles / 21 minutesbrbrBlue Grass Airport – 18 miles / 24 minutesbrbrDowntown Lexington & Rupp Arena – 19 miles / 29 minutesbrbrHistoric Frankfort (Kentucky’s capital) – 7 miles / 14 minutesbrbrMidway itself is known for its quaint downtown lined with local shops, antique stores, and farm-to-table restaurants. It’s the perfect place for horse enthusiasts, bourbon trail explorers, or anyone wanting to experience authentic Kentucky charm. Whether you’re here for the horses, the bourbon, or simply a relaxing getaway, you’ll be in the middle of it all.brbrYou will access the home with a code given to you by your hosts. brbrThe SpacebrbrThis brand-new luxury condo sits above a working barn and offers the perfect mix of comfort and countryside charm. The open-concept living area features a full kitchen stocked with everything you need—Keurig with frother, blender, crockpot, air fryer, toaster, tea kettle, dishwasher, mixing bowls, microwave, pots & pans, ice bucket, and bar carts. The living room has a Smart TV, where you can log in to your own streaming platforms and enjoy a cozy night in.brbrThere are three bedrooms in total:brbrTwo bedrooms each feature a king bed and Smart TV.brbrOne bedroom includes a twin trundle bed, Smart TV, and a convenient desk for work or study.brbrStep outside onto the patio, where you’ll find comfortable seating and a propane grill, perfect for relaxing evenings overlooking the farm animals.brbrPlease note: this property is located on the second floor and is only accessible by stairs.brbr Pets: Dogs may be accepted with prior approval.br Horses: Guests are welcome to bring their horses and use the stalls in the barn below. If you choose to do this, it is a $50 charge per stall! You MUST INFORM US if you choose to use this amenity. (Guests are responsible for cleaning up after their animals.)brbrNO DOGS WITHOUT APPROVAL!!!! If we find out that you have ANY pets on the property, you will be fined!
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(1)

$525.24

/ Nightly
Private Vacation Home

Millstone Cape~Hot Tub~Game Room~12 min Keeneland

Midway, Kentucky, United States

Welcome to Millstone Cape. This spacious 4-bedroom home sleeps 10 and features premium amenities like a hot tub, game room, and a plush king bed. Tucked away on the outskirts of Lexington, you'll enjoy quiet nights while remaining minutes from Keeneland and the heart of downtown.brbrThe spacebrKey Features:brbr⟶ Sleeps 10br⟶ 4 bedrooms, 3 bathroomsbr⟶ 5 beds — ideal for large groupsbr⟶ Hot tub, outdoor dining areabr⟶ Located just 12 min to Keeneland and 16 min to Downtownbr⟶ High-speed internetbrbrTHE SLEEPING QUARTERS brbrFirst Floorbrbr• The Flex Suite: A bright and versatile bedroom that doubles as a private office. It features a comfortable Sofa Bed, making it the perfect easy-access spot for guests who prefer to avoid stairs or need a quiet space to work. A full bathroom is located just steps away for complete convenience.brbrSecond Floorbrbr• The Primary Retreat: An expansive bedroom featuring a plush King Bed and a Pull-out Sofa, offering extra sleeping space or a private lounge area. This room boasts its own private ensuite bathroom.brbr• The Queen Room: A serene and inviting bedroom with a Queen Bed, perfect for couples.brbr• The Full Room: A cozy and well-appointed bedroom featuring a Full Bed.brbrNote: The Queen and Full rooms share a beautifully designed third full bathroom on this level.brbrBATHROOMS & AMENITIES brbrWith three full bathrooms strategically placed throughout the home, your group will have plenty of space to get ready for a day at Keeneland.brbr• First Floor: One full bathroom conveniently located near the Flex Suite and living areas.brbr• Second Floor: Two full bathrooms, including the private ensuite for the Primary Retreat.brbr• Stocked for Comfort: Every bathroom is supplied with premium, fluffy towels and high-quality shampoo, conditioner, and body wash. Each upstairs bathroom is stocked with a hair dryer, so you can save the suitcase space! The primary suite features a dedicated garment steamer for your convenience.brbrGATHER, PLAY & RELAX brbr• Dining & Connection: Our dining areas are built to bring people together. With ample seating for the whole group, it’s the perfect spot for long meals and even longer conversations.brbr• The Game Room: After a day on the Bourbon Trail, head to the ultimate hangout spot. Whether you're catching the big game, hosting a movie night, or challenging your friends to a Ping Pong tournament, this space is designed for high-energy fun.brbr• Living Spaces: If you're looking for a slower pace, our inviting living areas offer plush seating and a peaceful atmosphere—ideal for unwinding and recharging.brbrTHE OUTSIDE OASISbrbr• Al Fresco Dining: Our expansive backyard is surrounded by quiet farm country, offering a serene backdrop for outdoor dinners.brbr• The Spa: Top off the night with a soak in the soothing hot tub—the perfect front-row seat for stargazing over the Bluegrass.brbrGuest accessbrGuests will receive a 4-digit code to access the smart lock on the front door for a seamless and secure check-in experience.brbrOther things to notebrEXCLUSIVE ADD-ONS brbrTo make your stay as seamless as possible, we are pleased to offer the following bespoke services:brbr• Grocery Stocking: Skip the store and arrive to a fully stocked kitchen. We offer pre-arrival grocery pickup and stocking for an additional fee (subject to availability).brbrEXPLORE THE AREA brbrWhile you are in the heart of horse country, we highly recommend a visit to our neighbors:brbr• Saxony Farm: Located just a short drive (or walk) away, Saxony Farm offers a stunning and intimate look at a working Thoroughbred farm. It is a fantastic place to tour and experience the heritage of the region firsthand.
Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
Slider Thumb
Exceptional(49)

$487.81

/ Nightly
Cottage

Discover Your Perfect Getaway: Cottage in the Heart of Horse & Bourbon Country!

Midway, Kentucky, United States

Welcome to our cozy cottage, your perfect getaway in the heart of Bourbon and Horse Country! We're thrilled for the opportunity to share our little slice of paradise with you. brbrYou will love this newly built (2020) country cottage near Midway, Versailles, Lexington, Georgetown, and Bluegrass Airport. brbrOur guests rave about the cottage's beautiful decor and incredibly comfortable interior. Whether you're here for a relaxing stay or to explore the local attractions, we're here to make your experience unforgettable!brbrPicture yourself starting your day on our lovely front porch, sipping coffee. You’ll hear the soft rustle of leaves, the cheerful chirping of birds, and perhaps catch a glimpse of horses grazing next door at Saxony Farm. This tranquil setting is perfect for a relaxing breakfast or a sunset.brbrIf you're a fan of bourbon tours, you're in luck! We’re close to Castle and Key, Woodford, and Buffalo Trace. Adventure seekers will love being on the Horsey 100 Trail, and sports enthusiasts can catch University of Kentucky football and basketball games nearby. Don’t forget to check out Wallace Station, KY Castle, and Keeneland while you’re here!brbrbrSleeps 6:brbrRoom 1: This room is on the first floor with one King bed, a large walk-in closet, a private full bathroom with a shower—a Roku TV in the room.brbrRoom 2: This room is on the first floor with two twin beds. A shared full bathroom with tub and shower.brbrRoom 3: This room is located in the loft and has a King bed and oversized dresser for maximum storage. A half bath upstairs is shared with the loft area—a Roku TV in the room.brbrLoft: Large area used for a home office, game time, or the extra space needed when multiple families prepare for their evening outings. brbrHighlights:brHuge loft for private adult or teen area. Massive front porch for relaxing, dining, or games. Beautiful views of the sunset or enjoying the night sky.brbrOur cottage is great for family nights, visiting local attractions, and Keeneland weekends. Space perfect for special occasions and multiple family getaways. brbrKitchen:brThe kitchen is stocked with All-Clad pots and pans, cooking utensils, dishes, Keurig and Drip coffee maker, a toaster, a microwave, an electric skillet, a crockpot, an electric stove, a dishwasher, and a refrigerator/freezer. One cabinet is dedicated to barware. Wine opener, shot glasses, stemless Yeti wine glasses, Derby glasses, and more.brSecurity: Our cottage has a Ring doorbell at the back entrance of the property that is monitored while unoccupied. The front driveway Ring can be manually turned off by using the switch at the front door labeled RIng. This will also turn off the security light at the front of the home. br brGreat location for UK Football, Keeneland Racing or Sales, and Kentucky Horse Park. It is also only 45 minutes from Louisville. brbrAs you drive to our cottage, allow enough time to admire the scenery. brYou will travel down Old Frankfort Pike, a Scenic Byway and home to Three Chimneys, Darby Dan, and Lane's End farms. brbrYou’ll find everything you need for a comfortable stay. Whether you're coming for a special occasion, a family getaway, or to escape the hustle and bustle, our cottage provides the perfect haven.brbrUltimately, your stay here will be filled with warmth, laughter, and unforgettable memories, making it a place you’ll look forward to returning to time and time again. brbrWe can’t wait to welcome you and help you create your own story here in beautiful Bourbon and Horse Country!
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb

$92.29

/ Nightly
Private Vacation Home

Midnight Train to Midway

Midway, Kentucky, United States

Make some lasting memories at our 'Midnight Train to Midway'!brThis unique place has a style all its own. The darling home sets on a large lot with view of the train tracks that run through the downtown area of Midway. Enjoy being at the end of a quiet street with all the amenities you need to enjoy your stay, while visiting this beautiful part of Kentucky close to many stops on the Bourbon Trail. With a King and a Queen bed to rest your head.brPlease do not smoke inside the home, if you do we will have to issue a $250 smoking fee.
Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
Slider Thumb

$87.64

/ Nightly
Private Vacation Home

The Bluegrass Railway Inn

Midway, Kentucky, United States

This unique place has a style all its own. The darling home sets on a large lot with view of the train tracks that run through the downtown area of Midway. Enjoy being at the end of a quiet street with all the amenities you need to enjoy your stay, while visiting this beautiful part of Kentucky close to many stops on the Bourbon Trail.brbrThis one level home has been recently remodeled with updated kitchen and bath, granite counters and new appliances.brbrThe entire house is available for your use. The home has a shared driveway with the neighboring home but plenty of space for everyone to park.brbrNeighborhood close to the train tracks and .3 miles to Downtown Midway.brPlease do not smoke inside the home, if you do we will have to issue a $250 smoking fee.
Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps

Home Most popular vacation rentals in Midway

Slider Thumb

$296.36

/ Nightly
Private vacation home

Bit and Bourbon

Midway, Kentucky, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
Slider Thumb

$1451.50

/ Nightly
Private vacation home

HOLIDAY HOUSE - Kentucky Bluegrass Home on Champion Thoroughbred Farm

Midway, Kentucky, United States

Bed 5

Bed

Bath 4

Bath

Sleep 8

Sleeps
Slider Thumb

$597.14

/ Nightly
Private vacation home

Charming 3-bedroom house in Midway with screened in porch and salt water pool!

Midway, Kentucky, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
Slider Thumb

$551.20

/ Nightly
Private vacation home

Family-friendly newly built house in the heart of Kentucky's Horse Country

Midway, Kentucky, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
Slider Thumb

$525.24

/ Nightly
Private vacation home

Millstone Cape~Hot Tub~Game Room~12 min Keeneland

Midway, Kentucky, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
Slider Thumb

$487.81

/ Nightly
Cottage

Discover Your Perfect Getaway: Cottage in the Heart of Horse & Bourbon Country!

Midway, Kentucky, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb

$400.24

/ Nightly
Private vacation home

Welcome to FarRhode Stable! A new, charming, 3 bedroom, 2-bathroom luxury condo perched above a beautiful barn. You will feel like a true Kentuckian with the gorgeous views of horses, cattle, donkeys, & even ducks! Book now for a perfect stay!

Midway, Kentucky, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb

$324.30

/ Nightly
Private vacation home

Fire Pit + Yard: Peaceful Bluegrass Escape!

Midway, Kentucky, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
Slider Thumb

$299.03

/ Nightly
Private vacation home

Bourbon Trail, Horse Park & Farms, Keeneland, Vineyard & Winery

Midway, Kentucky, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
Slider Thumb

$296.15

/ Nightly
Private vacation home

Charming Cottage Conveniently Located In The Heart Of Horse And Bourbon Country

Midway, Kentucky, United States

Bed 3

Bed

Bath 2

Bath

Sleep 7

Sleeps

Most Popular Cities in Kentucky