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Vacation rentals in Midway

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Quick stats about vacation rentals in Midway

  • Total vacation rentals

    Explore 10 vacation rentals in Midway

  • Nightly prices starting at

    Midway vacation rentals start at R 1,132 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 1,040 verified reviews to help you choose

  • Wi-Fi availability

    10 of Midway vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Midway rentals

  • 4.9 Average rating

    Midway stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated vacation rentals in Midway

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A well-equipped kitchen features dark wooden cabinetry and granite countertops. Four barstools with cushioned seats are arranged around a large island. Stainless steel appliances, including a refrigerator and oven, are visible alongside natural light streaming through a window.
Cabin in Frankfort

On The Rocks

Ultimate in privacy, yet two minutes from downtown Frankfort! This cabin-style home (think Gatlinburg!) sits on three wooded acres. Long, rambling decks on three sides (one covered, one fully screened, one open air). Our adjacent farm surrounds the property, making it even more private. This home sits high on a bluff above downtown Frankfort & the Kentucky River (our farm borders on the river). Just three miles to Buffalo Trace Distillery (if you could fly, it's way closer than that!)

5.0 out of 5 average rating, 247 reviews
Top guest favorite
A seating area is furnished with two brown recliners and a matching couch, arranged around a light area rug. A television is placed on a wooden stand against the wall. Framed artwork decorates the neutral-colored walls, contributing to a cozy atmosphere.
Apartment in Georgetown

Private Farm Basement Apartment!

Basement apartment located on 5 acres in Central Kentucky! Full and private kitchen, dining& living; laundry available on main level of home if needed, 1BR with attached BA. Step outside your private entrance to the shared back yard and patio space. 6 minutes from the KY horse Park and 2 minutes from interstate 64. Pets welcome with non refundable deposit/ cleaning fee. Pet must be with you at all times or crated There are 3 dogs on property will only be in shared yard Trailer parking ok

4.94 out of 5 average rating, 109 reviews
Top guest favorite
A charming cottage exterior is framed by a large tree, with a well-maintained lawn and shrubs lining the front. The entrance features a porch with a welcoming door and matching window shutters, all under a sloped metal roof.
Home in Midway

Country Cottage in Horse and Bourbon Country

This completely updated cottage is located on a scenic byway voted one of the ten best scenic drives in the United States, on which you will see thoroughbred farms for which Kentucky is famous. Keeneland and the Kentucky Horse Park are within 20 minutes. There are 4 distilleries within 10 miles, 11 within 30 miles, and 23 within an hour’s drive. Two bedrooms, new kitchen, new bathroom, washer and dryer, covered porch, deck, air conditioning, wifi, cable TV, and ample parking. Relax and enjoy!

4.99 out of 5 average rating, 152 reviews
Top guest favorite
A charming exterior view of a single-story home is framed by a white picket fence, with a small seating area accessible by the entrance. Trees with autumn foliage create a colorful backdrop, and a clear blue sky enhances the welcoming appearance of the residence.
Home in Georgetown

The Clayton House | Chic & Cozy

Welcome to our stylish, newly renovated 2-bedroom, 1-bath home, centrally located just minutes away from Georgetown College! This spacious gem boasts an inviting open full-kitchen and living room concept, a back patio, and back yard. Whether you're visiting the college, exploring the town, or simply looking for a comfortable and modern retreat, The Clayton House is the ideal choice for your stay. Experience the perfect blend of convenience and comfort in this newly revitalized space. *No pets

4.92 out of 5 average rating, 133 reviews
Top guest favorite
A charming two-story home features white siding and dark shutters, framed by lush greenery and seasonal decorations. A welcoming path of brick leads to the entrance, where decorative pumpkins add a touch of warmth, inviting guests to explore the property.
Home in Midway

The Bees Wing

Built in 1889 this 2800 sq ft home has lots of charm and plenty of space to accommodate up to 8 guests. With two king beds, a queen, two twins, a pull out sofa bed, plus three full baths, dining room, living room, completely remodeled kitchen, plus a spacious screened in porch overlooking the 16 x 40 in ground salt water pool and fabulous backyard, what more could you ask for in the heart of horse country? The heart of Midway with its renowned restaurants and galleries is just a block away!

4.99 out of 5 average rating, 107 reviews
Top guest favorite
The cottage exterior is framed by lush greenery and a neatly maintained lawn, featuring a charming porch with rocking chairs. A stone pathway leads up to the entrance, surrounded by trees and open space, providing a serene rural setting.
Home in Lexington

Charming Cottage Home on a Horse Farm in the City!

Charming cottage on a 20-acre horse farm just minutes from Downtown Lexington, Midway, Keeneland, the Horse Park, and LEX Airport. Enjoy country calm with city convenience and quick access to I-64/I-75 for Bourbon Trail trips and visits to Louisville or Cincinnati. The cottage offers a one bedroom with a king size bed and two twin beds total of 4 guest maximum, full kitchen, living area, WiFi, cable TV, and total privacy. Dogs welcome with prior approval- PET FEE is 35.00 PER DAY/ PER DOG

4.94 out of 5 average rating, 179 reviews
Top guest favorite
The exterior of The Dew Drop In is framed by two large trees, showcasing a well-manicured lawn. The house, painted in light colors, is set back from the foreground, with a wraparound porch visible. A wooden fence outlines the property, enhancing the natural setting.
Farm stay in Midway

Saxony Farm - The Dew Drop In

Nestled in the heart of Kentucky's 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.

5.0 out of 5 average rating, 132 reviews
Top guest favorite
Barn in Georgetown

New! Horse Farm stay! On Bourbon Trail!

The Loft at Pine Knoll Farm Kentucky is a unique horse farm stay located above our beautiful horse barn in the heart of horse country. We have prime views of the farm which is located in the center of the Bourbon Trail. 5 min to great restaurants in Midway! The Loft is 15 mins to The Kentucky Horse Park, 25 mins to Keenland, and Ark is 50 mins. Stabling/turnout available. We offer horse experiences/workshops/clinics through Kentucky Horse Experiences. Sign up to meet The Peace Ponies!

4.98 out of 5 average rating, 100 reviews
Top guest favorite
The duplex features a brick exterior with a welcoming entrance flanked by lush green grass and flower beds. Large windows provide natural light, and the surrounding trees offer a serene backdrop to this spacious home.
Guest suite in Stamping Ground

Spacious and quiet Grandma's Duplex

Roomy, out-of-town duplex, within 7 minutes of downtown Georgetown, KY. You will see farmland and livestock on your drive to your stay with us. We are 40 min from The Arc Experience; 15-25 minutes to Lexington attractions like the KY Horse Park, Keeneland, UK & Rupp Arena! Large rooms throughout. Queen bed in the master suite with a king bed in the guest bedroom, full eat-in kitchen and washer/dryer available. Great place for extended-stay, especially with the applicable discount!!

4.84 out of 5 average rating, 258 reviews
Top guest favorite
A serene landscape showcases a gravel path winding through lush green grass, framed by wooden fences. A large tree stands prominently, with the sun rising in the background, casting a warm glow across the misty field under a softly clouded sky.
Home in Versailles

Quaint little farm house close to Keeneland/horses

Remodeled beautiful 1900s 2 story house on farm surrounded by Creek and fire pit for your convenience. LOCATION, LOCATION!!! This is the perfect example of having the country in the city! If you are wanting the true feeling of relaxation, this is for you. Amazing views, and close to many famous attractions. 5-10 minutes away... Keeneland The Kentucky Castle Bluegrass Airport Castle Hill Winery Aviation Museum Eckert Orchard also.. Restaurants, Wineries, Breweries, Bourbon Trails

4.95 out of 5 average rating, 246 reviews
Top guest favorite
A serene outdoor area is highlighted by a covered patio featuring comfortable seating and a hot tub. Ambient lighting creates a cozy atmosphere, while lush green grass and carefully placed shrubs enhance the inviting outdoor space.
Home in Georgetown

The Luxe/Hot Tub/12min to Horse Park/30 Min to Ark

Where elegant vintage meets modern design. Come and enjoy this historic home on a quiet street in downtown Georgetown. You will be within walking distance of shops, restaurants, Georgetown College, and parks. Home is also a ten minute commute to the Kentucky Horse Park and interstate. Equipped with a fully stocked kitchen, full dining room, and a Loft office space. You can enjoy your Private backyard oasis boasting a relaxing hot tub, fire pit, black stone grill, and outdoor tv.

4.96 out of 5 average rating, 202 reviews
Top guest favorite
The exterior of the historic white brick building is visible, showcasing large windows and a covered entrance. Green grass surrounds the property, with a pathway leading to the front steps. A quiet neighborhood atmosphere is depicted with utility poles and nearby structures in the background.
Apartment in Midway

Downtown Midway Loft--Walk Everywhere!

Located in the heart of downtown Historic Midway, this renovated studio apartment makes for the perfect retreat. The bedroom features a queen sized Tempur-Pedic mattress, ROKU TV, and desk. Plan your day with a morning coffee in the full kitchen that's equipped with basic cookware for prepping light meals. The apartment is located on the third floor, so pack light as it is accessed only by stairs. We are delighted to host your stay in beautiful Kentucky!

4.93 out of 5 average rating, 145 reviews

Popular amenities for Midway vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Midway

Top guest favorite
A spacious dining area is highlighted by a large wooden table surrounded by several chairs. Barn-style sliding doors lead to a well-lit area filled with natural light. A piano and a decorative cabinet are visible along one wall, adding to the inviting atmosphere.
Home in Midway

Midway Cottage-Vineyard, Bourbon Trail, Horses

4.99 out of 5 average rating, 91 reviews
Top guest favorite
A modern kitchen is presented with light cabinetry and a prominent granite countertop. Three red bar stools are situated at the kitchen island, complementing the sleek stainless-steel appliances and decorative fixtures. Warm lighting enhances the inviting atmosphere, while the tile backsplash adds a stylish touch.
Home in Midway

Midway Meadows Downtown on the Park

4.96 out of 5 average rating, 70 reviews
Top guest favorite
Home in Midway

Millstone Cape~18 min to UK~Game Room~Hot Tub

4.95 out of 5 average rating, 22 reviews
Top guest favorite
The cabin is set amidst a grassy yard, showcasing a wooden exterior with a stone chimney. A covered porch with a railing is visible, featuring an umbrella. Surrounding greenery enhances the peaceful setting.
Cabin in Midway

Kentucky breeze cabin

4.98 out of 5 average rating, 52 reviews
Superhost
Home in Midway

Rosalyn's House

5.0 out of 5 average rating, 4 reviews
Guest favorite
A cozy bedroom features a black metal bed frame supporting a spacious bed adorned with a floral comforter and decorative pillows. Natural light enters from the doorway, highlighting the crisp, neutral wall color and the wooden floor beneath.
Farm stay in Midway

Kentucky Horse Country Getaway

4.92 out of 5 average rating, 61 reviews
Guest favorite
A refreshing inground pool is set against a backdrop of rolling hills and greenery. Lounge chairs under umbrellas provide seating options. Decorative pink flowers in planters frame the pool area, while large inflatable floats add a playful touch to the water.
Home in Versailles

Sugar Hill Farm-Gorgeous Farmhouse w FirePit

4.9 out of 5 average rating, 48 reviews
Guest favorite
A charming cottage is set within a rural landscape, surrounded by trees and open fields. A cow grazes nearby, and large windows invite natural light into the living space. The entrance features a welcoming porch area with seating and a clear view of the tranquil surroundings.
Cottage in Lexington

Springwood Cottage in the heart of the Bluegrass.

4.96 out of 5 average rating, 69 reviews

Frequently Asked Questions

  • How much does it cost to stay in house rentals in Midway?

    Experience the best of Midway with our house rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Midway have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Midway. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Midway have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in Midway. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Midway have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Midway. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Midway have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Midway. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Midway?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with free parking, over 10 homes with a kitchen, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore