Places to stay in Midway

4.97 out of 5 average rating, 112 reviews

A spacious living area features a circular gold leather couch surrounding a suspended fireplace. Exposed wooden beams and original brick walls enhance the character of the loft. Soft seating and decorative cushions invite relaxation, while the unique patterned wall adds visual interest.

Loft in Shelbyville

Transportation Included For A Day/ Up to 14 PPL

Best place to stay on the Bourbon Trail FEATURED on HGTV! Swanky! Stunning! Spectacular! You'll be in a top-floor loft overlooking downtown Shelbyville and perfectly situated in the heart of the Bourbon Trail! Incredible place to stay for Derby, Keeneland, PGA or local weddings and events---if you can pry yourself away from here! We specialize in making your stay an over-the-top experience and are happy to arrange chauffeured transportation, private chef accommodations, and dinner reservations.

5 out of 5 average rating, 30 reviews

Home in Springfield

Walk to dinner! Best bourbon location! Hottub!

🥃 Bourbon Trail Distilleries & History Maker’s Mark Distillery Limestone Branch Dist. / Yellowstone Willett Distillery Heaven Hill Bourbon Experience Lux Row Distillers Preservation Distillery Bardstown Bourbon Company ALL UNDER 20 MILES! 🌳 Parks & History * Lincoln Homestead State Park My Old Kentucky Home 🍷 Wineries* Jesters Winery McIntyre’s Winery 30-50 Miles 30 Wilderness Trail Distillery 30 Jim Beam American Stillhouse 50 Buffalo Trace Distillery 50 Woodford Reserve

4.91 out of 5 average rating, 121 reviews

The kitchen features light wood cabinetry and modern appliances, including a stove and dishwasher. A window above the sink allows natural light to illuminate the space. The open plan connects the kitchen to the living area, creating a spacious environment.

Condo in Shelbyville

Kentucky bourbon, horses, cozy condo

Welcome to your home away from home! Great place to stay while visiting local establishments, horse shows, bourbon trail, extended work stay or family. Work or Play this adorable condo was recently renovated and has all the comforts of home! King bed in main bedroom with full bath, queen size guest bed and 2nd large bathroom, wifi, fully furnished kitchen along with washer and dryer. Parking at your entrance with no steps! Just minutes from I64, groceries, restaurants and shopping!

4.94 out of 5 average rating, 51 reviews

An outdoor patio area features a cozy arrangement of four wicker chairs with light cushions surrounding a glass-topped table. A hot tub is placed against a wooden backdrop, with warm string lights hanging overhead, creating a relaxing space.

Home in Lexington

Magnolia Molly | Rupp Arena, Distillery District

Welcome to Magnolia Molly - a peaceful and centrally located home. Our 2-bedroom property sleeps 4-6 guests and has ample entertaining and relaxation space. Walk to all the Distillery District has to offer: delicious restaurants, coffee, craft beer, and the Burl music venue. Located 5 minutes from downtown Lexington, Rupp Arena, and Red Mile. Drive just 10 minutes to Kroger Field, Keeneland, & the airport; 20 minutes to KY Horse Park. 2 security cameras on premises at points of entry.

4.93 out of 5 average rating, 249 reviews

A serene landscape captures grazing horses in a lush green pasture, bordered by a traditional wooden fence. The early morning fog blankets the distant trees, while a soft orange and pink sky indicates sunrise, creating a tranquil and picturesque setting.

Home in Harrodsburg

Kentucky Horse Farm Barndo On The Bourbon Trail

My place is close to Shaker Village, Old Fort Harrod State Park, Historic Beaumont Inn, Bright Leaf Golf Course, Pioneer Playhouse, Perryville Battlefield State Historic Site, Danville KY, Centre College. You’ll love my place because of the views, the location, the horses, the ambiance. My place is good for couples, solo adventurers, business travelers, and families (with kids). Also close to Four Roses Distillery, Wild Turkey Distillery, Wilderness Trail & Buffalo Trace & Makers Mark

4.94 out of 5 average rating, 180 reviews

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

5 out of 5 average rating, 8 reviews

The exterior of the home presents a charming facade with white siding and brown shutters framing two windows. A green door welcomes guests, flanked by small evergreen shrubs. Stone steps lead to the entrance, surrounded by seasonal foliage.

Home in Shelbyville

WelcomeTreatsWaiting| CentralLocation| Comfortable

Cozy 750 sqft home designed for convenience and comfort 1 bdrm w/ comfy queen bed, 1 bath and a pull out couch Stocked w/ snacks, toiletries, and coffee & tea options Outside enjoy the fire pit (wood provided) or fire up the grill for a burgers or steak Located across from the fairgrounds in safe, charming downtown Shelbyville, you'll have easy access to local events, dining, and shopping Whether you're here to explore the Bourbon Trail or just unwind this spot offers everything

4.98 out of 5 average rating, 157 reviews

A corner of the room features a green accent chair beside a round table, which holds glassware and books. A woven plant pot contains a leafy plant, while a textured throw blanket rests on the chair. Natural light brightens the space.

Loft in Frankfort

The Loft - Cozy Retreat in Historic Downtown

Experience the warmth and comfort of The Loft—your top-rated retreat just 8 minutes from downtown. Walk to the Capitol, explore nearby sights, and enjoy horse country close by. Relax in a cozy bed, unwind on a comfy couch, and enjoy modern updates in your private second-floor apartment. With parking at the door and a welcoming hygge vibe, it’s perfect for recharging. Just minutes from 13 distilleries, The Loft is your ideal base for exploring the Bourbon Trail in comfort and style.

4.99 out of 5 average rating, 68 reviews

A welcoming living room features a light-colored sofa adorned with decorative pillows. A large mirror enhances the natural light from the windows, while a coffee table and two accent tables provide functionality. Plants and soft textures add warmth to the space.

Home in Georgetown

The George- Beautifully Furnished, Walk Downtown

Located in downtown Georgetown, this lovely historic home has been freshly updated and is centrally located to all of the area attractions! This property offers a fully stocked kitchen, work space, a great back yard, and laundry. We also provide Matrix hair products, Buff City soaps, and Starbucks coffee (we like to spoil our guests)! Short walk to the great shops and restaurants downtown and Georgetown College. Care-free checkout- no chores! We can't wait to have you here!

4.94 out of 5 average rating, 516 reviews

The charming exterior of the cottage is highlighted by two symmetrical windows and a central door framed with dark wood. Lush greenery properties a potted plant atop a rustic barrel and vibrant flowers adorn the window boxes, enhancing the inviting entrance.

Guesthouse in Lexington

The Bourbon House- Downtown Lex’s Premier Air B&B

Welcome to "The Bourbon House" Downtown Lexington's Premier spot to stay for an authentic Kentucky experience. This cottage was built by me from the ground up with no details spared to immerse my guests in the finest things Kentucky has to offer- Fully stocked bourbon bar mixers! (You supply bourbon) Hand crafted house and furnishing from reclaimed wood and bourbon barrels, private hot tub, bathrobes, garden, fire pit, and walking distance to downtown and Rupp arena

4.95 out of 5 average rating, 307 reviews

A modern bathroom is displayed, featuring a sleek vanity with blue cabinets and a light countertop. A shower area with white tile and a wood step is visible. Large windows provide natural light, and stylish artwork is hung on the walls, complemented by a small dining table with a black chair.

Townhouse in Lexington

LUX TownBranch Retreat 💙 Downtown w/ Tempur-Pedics

Welcome to your Kentucky Home This beautifully remodeled 2nd floor historic property is located in Downtown Lexington. Walk to Rupp Arena, several cool bars/breweries and upscale restaurants. Smart TV's and high speed internet service. Beautiful kitchen with gas range and stainless steel appliances. * Rupp Arena - 1 mile * Keeneland Racetrack - 7 miles * Kentucky Horse Park - 8 miles * STR Reg #15062369-6 - Maximum occupants 8

4.94 out of 5 average rating, 111 reviews

The spacious bathroom features elegant dark stone tiles and a large soaking tub positioned under an arched window. Two vintage-style vanities with sink basins are complemented by decorative mirrors. A separate shower enclosure is visible, and a toilet is placed discreetly in the corner.

Condo in Paris

Paradise Inn B&B - Lover's Suite

The only B&B in Kentucky with an ‘Eiffel Tower’ view! Paradise Inn B&B is a unique penthouse suite atop "The World's Tallest Three Story Building" (from Ripley's Believe It or Not!) with exquisite oriental decor from the far East. The unbeatable hospitality is provided by your host and the owner, Lee Nguyen. This stay includes a $25 gift certificate for Paradise Cafe - Asian fusion and Pho restaurant located on the first floor.

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Popular amenities for Midway places to stay

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Midway's top sights

Equus Run Vineyards18 locals recommend

Heirloom Restaurant11 locals recommend

Holly Hill Inn14 locals recommend

The Brown Barrel & Blind Harry's12 locals recommend

The Goose & Gander4 locals recommend

Darlin Jean's Apple Cobbler Cafe9 locals recommend

Other great vacation rentals in Midway

4.98 out of 5 average rating, 144 reviews

An outdoor patio features two black lounge chairs positioned around a small white table. A fire pit with flames adds warmth to the setting, surrounded by a grassy area and scenic views of distant trees and hills, with a colorful sky at sunset.

Cabin in Mount Eden

Bourbon Country Cottage

4.89 out of 5 average rating, 122 reviews

Cottage in Taylorsville

Best view of the lake two bed two bath cottage #4

Cottage in Spencer County

Aerial view captures Taylorsville Lake, surrounded by lush greenery and autumn foliage. The winding shoreline is visible alongside the marina with several boat docks. The community road runs beside the scenic landscape, providing a clear view of the serene water and rolling hills.

4.91 out of 5 average rating, 151 reviews

Peaceful Cottage Minutes from Lake Access

4.94 out of 5 average rating, 181 reviews

Cottage in Harrodsburg

Paradise Cottage Enjoy lake Views and Lake Access!

4.84 out of 5 average rating, 37 reviews

An exterior view of a modern patio area features stacked stone benches surrounding a fire pit. A black metal staircase leads to an upper level, framed by textured brick walls and lush greenery. Paved pathways extend through the outdoor space.

Apartment in Lexington

Count Fleet @ 3Forty /2BR Apt/ Walk to Rupp Arena

4.97 out of 5 average rating, 108 reviews

Home in Lexington

Hot Tub | Great Location | Patio | Grill | Ping Po

4.71 out of 5 average rating, 166 reviews

Cottage in Taylorsville

Get Away From It All