Holiday houses in Middleburg

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Top-rated holiday rentals in Middleburg

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Top Guest favourite
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, 103 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 favourite
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, 175 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 favourite
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, 408 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 favourite
A cozy cottage is framed by a large tree with blooming white flowers. The exterior features a light-colored facade and a front porch, with a swing and a small pet visible on the grassy lawn. Windows with dark shutters add character to the home.
Cottage in Liberty
4.88 out of 5 average rating, 73 reviews

Seven Oaks Cottage

Cozy cottage nestled in the valleys of Casey County. It’s semi rural location offers the best of both worlds, the peace that comes with farm views of our Scottish Highland cattle and easy access to all that Liberty has to offer. Located 3.5 miles from dining, shopping, a movie theater and groceries. Only another 2 miles to Central KY AgExpo Center access. Situated between the cottage and downtown is also the beautiful Lake Liberty where you can find hiking trails and picturesque views.

Guest favourite
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, 48 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 favourite
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, 214 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 favourite
The exterior of a spacious property is showcased at night, illuminated by soft outdoor lights. The architectural design features a steeply pitched roof and large wooden beams. A well-maintained lawn lies in front, with a welcoming entry that leads to multiple porches.
Home in Kings Mountain
4.84 out of 5 average rating, 45 reviews

The Bunkhouse

The whole group will enjoy easy access to everything from this centrally located property. It’s 8 miles from Highway 27, and 8 miles from Liberty & Tarter Industries on 127. This 4 acre property is perfect for multiple family get-togethers, Business Meetings, and Parties. Inquire about the fees for those uses. Meals can be provided at extra cost. See Menu. Lake Cumberland & Herrington Lake are about 30 minutes away and Lake Liberty is approximately 9 miles away.

Guest favourite
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, 188 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 favourite
The cottage exterior features a covered porch with a dark bench and decorative mum plants. Large windows allow natural light into the space, while the metal roof provides durability. A spacious lawn extends, revealing open pasture land in the background.
Home in Knifley
5 out of 5 average rating, 13 reviews

Haney’s Hideaway close to Green River Lake

Country cottage just minutes from Green River Lake boat ramp. Quiet peaceful setting to relax and unwind with lots of free parking. WiFi included and smart TVs in each bedroom and living room. Family friendly with large yard. Eat-in kitchen fully stocked with all the dishes and pots/pans you will need! Full-size washer and dryer onsite

Guest favourite
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 favourite
A modern farmhouse presents a striking black exterior under a clear sky. The building features a sloped roof and large steps leading to an inviting entry. Surrounding green grass and mature trees enhance the rural setting, contributing to a serene atmosphere.
Farm stay in Danville
5 out of 5 average rating, 20 reviews

Your Home at Nossa Farms

Relax and unwind on a charming farm, where wide open pastures and delightful company await you. Watch curious chickens, playful ducks and cattle graze as you unplug and immerse yourself in the tranquility of nature. Enjoy the perfect balance of peaceful rural charm while staying conveniently close to local attractions.

Top Guest favourite
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, 88 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.

Popular amenities for Middleburg holiday rentals

  1. Airbnb
  2. United States
  3. Kentucky
  4. Casey County
  5. Middleburg