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Vacation rentals in Middleburg

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Top-rated vacation rentals in Middleburg

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

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Guest favorite
A spacious living area features a modern sofa with decorative pillows. Large opening doors showcase views of the covered porch and surrounding greenery, allowing natural light to fill the space. A wall-mounted television and fireplace are also present, enhancing the inviting atmosphere.
Home in Somerset
4.95 out of 5 average rating, 143 reviews

Garage Door to the Wilderness!

Welcome to this stylish and sleek tiny home that's perfect for modern living! With ample space to sleep 4, features a bathroom complete with a beautifully tiled custom shower. The kitchen is a chef’s delight, black cabinetry and elegant granite counters.Enjoy the seamless flow of heated tile flooring throughout, leading you to the covered back porch where you can sip your morning coffee! The back garage door offers easy access to nature’s beauty. Located 5 minutes from either town or the lake!

Top guest favorite
A ranch-style home is depicted with a light green exterior and dark shutters. A spacious covered front porch features two rocking chairs and a welcoming entryway, while neatly landscaped shrubs and grass surround the brick pathway leading to the front door.
Home in Danville
4.99 out of 5 average rating, 118 reviews

Walking distance to Centre, Main Street, hospital

Grant Place is a 2 bedroom, 2 full bathroom home located on a quiet street within walking distance to Centre College, Norton Center, Ephraim McDowell Hospital and Main Street. Located 4 miles to Wilderness Trail Distillery and 14 miles to Shaker Village. Grant Place is spacious and fully furnished with a well-stocked kitchen. The home features one king bed and one queen bed. We do provide a pack and play if you are traveling with a small child. Enjoy relaxing on our large covered front porch.

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, 249 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.

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
4.97 out of 5 average rating, 108 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.

Top 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, 52 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.

Guest favorite
A welcoming living area features a dark sofa and an armchair with a light blue cushion. A wooden coffee table sits on a decorative area rug. Natural light enters from the sliding glass doors, highlighting the floral artwork on the wall.
Apartment in Campbellsville
4.99 out of 5 average rating, 168 reviews

Grace Land

Grace Land is a newly renovated apartment. Located just outside the city limits of Campbellsville. We offer a fully equipped kitchen with a Keurig for fresh morning coffee and a variety of coffee flavors provided. King size bed in bedroom and a Lazy Boy sofa bed in the living room. Tv with Cable, Netflix, and Wifi. Covered patio area. 3 miles from Green River Lake and Campbellsville University. 5 miles from Taylor Regional Hospital. Perfect for travel nurses. Keypad entry.

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, 219 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, 191 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 entryway features a striking artwork installation on the black wall, complemented by a spiral staircase leading to the upper level. Comfortable seating includes a tufted leather chair and a plush sofa, with a round wooden coffee table at the center on a decorative area rug.
Guesthouse in Somerset
4.98 out of 5 average rating, 195 reviews

Elegant Modern Rustic Retreat w/ Hot Tub

A steel framed industrial warehouse converted into an upscale two bedroom rustic-chic living space located within 8 miles of beautiful Lake Cumberland and within 5 minutes of Downtown, Somerset. The city is yours to explore from your own private 2 bed, 1 bath modern rustic retreat. Picture comfy beds, full bathroom, a kitchen built for entertaining, all under a metal tin roof for those rainy days when you just want to curl up and relax.

Top guest favorite
Home in Harrodsburg
4.94 out of 5 average rating, 174 reviews

The Betsy Sweat Cottage.

View the cottage on YouTube listed by the name of the cottage.This home is all Electric . Carbon Monoxide detector located beside bed .There is a KING SIZED bed. …..This is a Small Home. Close to Danville 9.5 miles (15 minutes away). , Frankfort 32 miles (40 minutes away) Lexington ****FYI- There is an additional charge of $30 extra charge for more than 2 guest.. children no extra charge.

Guest favorite
A cozy sleeping space features a spacious bed with a soft pink quilt adorned with subtle floral patterns. Natural wood walls create a warm ambiance, while a bedside lamp provides soft illumination. A window with blinds allows for light control.
Apartment in Liberty
5 out of 5 average rating, 5 reviews

Cosy Effeciency Studio Apartment

An efficient studio apartment. Queen size bed, Full size kitchen with French door refridgerator (Filtered water dispenser and ice maker). Cosy and convenient for a short stay or even long term stay. Dedicated parking spot. Within 10 minutes from downtown liberty, right on highway 49. Property sits on a 7 acre mini farm. You are allowed to fish from the pond.

Top 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, 145 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

Popular amenities for Middleburg vacation rentals

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