Vacation rentals in Middleburg

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Top-rated vacation rentals in Middleburg

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Top guest favorite

A charming house is set back from a peaceful country road, with a spacious porch that wraps around one side. A sign reading 'Country Charm' stands prominently in the front yard. The property is surrounded by green lawns and gentle landscaping.

Home in Stanford

4.96 out of 5 average rating, 243 reviews

Country Charm

This house is on a peaceful country road and has three bedrooms, two full baths, and a double driveway for parking. The newer appliances include a refrigerator, cook stove, dishwasher, and coffee makers. For your convenience, we provide the coffee for you to prepare. You will find water and soda in the refrigerator. Nearby are the Cedar Creek Lake, Lincoln County Fairground, and the Boyle County Airport. It's very near Stanford, Kentucky, about ten miles from Danville, and ten from Lancaster.

Top guest favorite

A charming country house is depicted, featuring a red metal roof and a welcoming porch. Two chairs are placed on the porch, overlooking a grassy yard. The backdrop reveals gentle hills under a clear blue sky, creating a serene outdoor setting.

Home in Knifley

4.99 out of 5 average rating, 101 reviews

The ranch house. Relax and unwind

Quiet, peaceful, country setting. There are country roads for walking and bike riding. For the boaters and fishermen, we are just minutes away from Arnold’s landing boat ramp and also Holmes Bend marina on beautiful Green River lake. For the hunting enthusiast, there are 20,000 plus acres of public land available for spring and fall hunting, with an abundance of turkey and deer. Close to Campbellsville University and Lindsey Wilson in Columbia. Lake Cumberland is also a short drive away.

Guest favorite

The exterior of the tiny house is presented, featuring a clean driveway and well-maintained lawn. Four outdoor chairs are arranged in a cozy seating area, surrounded by greenery and shaded by trees. The building displays a modern design with contrasting black and white elements.

Home in Somerset

4.91 out of 5 average rating, 170 reviews

Tandy Tiny House

Welcome to Tandy Tinyhouse! This Adorable 1Br is Brand New and has everything you need! Very Modern Kitchen w/tiled backsplash, Microwave, Keurig, Refrigerator, Range and Granite Counters. LTV Flooring and 10ft Ceilings throughout. En-suite features a Barn door and Tiled Shower. Washer/Dryer Combo just off of the Kitchen Area. Amazing location 3 minutes to Downtown Somerset and 10 minutes to Lees Ford Marina. You will want to stay here again and again! Please leave mini split 68 or above

Top guest favorite

A rustic cabin is nestled among vibrant autumn trees, positioned above a serene pond. A small dock with two chairs is visible near the water's edge, inviting relaxation. The surrounding landscape features lush greenery and colorful foliage, enhancing the cabin's secluded feel.

Cabin in McKee

4.97 out of 5 average rating, 400 reviews

Mountain Dream Cabin -Fish Pond+Fenced Yard+Stalls

Escape to a peaceful cabin with a wraparound porch perfect for soaking in the beauty of nature. This pet-friendly retreat features a fenced yard and space for trailer parking, plus four horse stalls available upon request. Enjoy catch-and-release fishing in the stocked pond, or explore nearby attractions: 25 minutes to Berea’s historic downtown and Pinnacle Trails, and 30 minutes to Flat Lick Falls and Sheltowee Trace. Unwind, explore, and experience the charm of our small-town getaway!

Guest favorite

The open-concept kitchen features white cabinetry with a marble countertop and a central island, seamlessly connecting to the cozy living area. A stone fireplace acts as a focal point, surrounded by comfortable seating and natural light flowing from nearby windows.

Farm stay in Hustonville

4.94 out of 5 average rating, 47 reviews

Farmhouse Escape at Smith Acres in Central KY

This beautifully renovated farmhouse offers a peaceful, romantic escape in the heart of Kentucky farm country. Tucked away on 65 acres at Smith Acres, it’s where rustic charm meets modern elegance. Whether you’re planning a family getaway, a weekend for two, or booking as part of a wedding celebration, you’ll find cozy spaces, sweeping views, and that sweet stillness that invites you to slow down and savor the moment. Perfect for reconnecting and making lasting memories together.

Top guest favorite

A comfortable living area features a gray sofa adorned with yellow accent pillows. A dark coffee table sits centrally, with a decorative cloche on top. Light curtains frame the window, and a flat-screen TV is mounted above a gas fireplace, enhancing the cozy atmosphere.

Guesthouse in Lancaster

4.99 out of 5 average rating, 212 reviews

Wishing Well Guesthouse On The Lake

A peaceful, waterfront guesthouse in a serene quiet neighborhood. On 2 acres of rolling hills, this choice location will be a peaceful getaway. Updated furnishings and appliances in this beautiful, open concept living space with a gas fireplace inside or a rustic fire pit outside. Close to lake marina rentals. #Center College #Pioneer Playhouse #Brass Band Festival #Pasture at Marksbury Farm #KY BBQ Festival #Bourbon Trail #Norton Center For The Arts #127 yard sale

Guest favorite

A well-lit outdoor space features a picnic table positioned on lush grass beneath trees adorned with string lights. A fire pit is visible nearby, creating a cozy ambiance for evenings spent outdoors.

Cabin in Science Hill

4.88 out of 5 average rating, 187 reviews

Small cabin close to town

Cabin was built by my grandparents about 40 years ago using timber cut from the land. Cabin is about 5 miles from town but feels country. Road is quite, with just local traffic, local being the people that live on the road. Very quite setting. Great place to relax where ever you find yourself, wither it is in the house, on one of the porches, or in the yard. House also has a fire pit in the back yard, & a charcoal gill if you want to grill out. We are pet friendly!

Top guest favorite

A spacious wooden deck surrounds the guesthouse, showcasing a modern architectural design with a vaulted roof. Comfortable seating and tables are arranged, complemented by potted floral arrangements. Large windows invite natural light, and the surrounding trees create a serene environment.

Home in Science Hill

4.97 out of 5 average rating, 117 reviews

TT’s Treehouse

Cozy studio guesthouse with beautiful oak vaulted ceiling overlooking scenic woods and creek just 10-15 minutes from boat ramp on Lake Cumberland. Covered porch around guesthouse with gas grill access. Kitchen fully stocked. Full size sofa couch, and 2 full size floor mattresses in loft. Free wifi available. Onsite boat parking available. Fire pit and fire table available-both outside. No smoking.

Guest favorite

A covered deck provides a view of the serene lake framed by trees adorned with autumn leaves. The tranquil water reflects soft light, while the surrounding landscape showcases a variety of foliage, creating a peaceful natural setting.

Cottage in Bronston

4.92 out of 5 average rating, 194 reviews

Cozy Cumberland Cottage

Cozy lake view cottage is perfect for a couple or family to enjoy Cumberland Lake. Relax on the covered back deck overlooking the lake at Burnside Marina. Short 10 minute drive to several restaurants, shopping, Burnside Marina or General Burnside State Park and drive in theater in Somerset. (No access to the lake from the property )

Top guest favorite

A bright sunporch is adorned with potted ferns and rustic decor. A red sofa is positioned against the wall, accompanied by two light-colored pillows. A pool table is visible in the background, with large windows allowing sunlight to illuminate the space. A ceiling fan hangs above.

Barn in McKee

4.98 out of 5 average rating, 199 reviews

Barn-house on the hill ⭐️Berea⭐️McKee

Treat yourself to a private getaway in this barn-house that combines country living with easy access to the best of Berea and McKee. From relaxing in the bright and airy sunporch while sipping on your morning coffee provided by the Keurig, to watching your favorite shows in the cozy TV room, you’ll certainly want to stay a while.

Guest favorite

The charming chalet is framed by lush greenery, featuring a wraparound porch with wooden railings. A welcoming front door is centered beneath a triangular roof. Flowering bushes border the stairs, leading to the outdoor seating area, which includes two chairs positioned beside the entrance.

Chalet in Liberty

4.92 out of 5 average rating, 142 reviews

Horse & Buggy Country Inn

Nestled on 3 acres in BEAUTIFUL Amish & Mennonite country...this ADORABLE chalet is the PERFECT getaway! Only minutes away from the local Amish & Mennonite stores! Only 6 miles from the Famous Bread of Life Cafe! Within 1 mile from The Galilean Children’s Home! Just minutes away from beautiful lake Cumberland and green river lake

Top guest favorite

A living area features a dark gray sectional sofa with decorative pillows facing a coffee table atop a soft area rug. A flat-screen television is mounted on the wall, and natural light enters through sheer curtains over the window. An entrance door is visible.

Home in Liberty

4.99 out of 5 average rating, 86 reviews

Home in Liberty

Enjoy easy access to everything from this 2 bedroom 1 bath home centrally located in the middle of Liberty. This non-smoking house has central heat/air. 1 mile to Ag Expo center, 5 miles to bread of life, 27 miles to lake Cumberland, 30 mins to Danville and only 1/4 mile for liberty’s Apple festival and court house.