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Holiday rentals in Middleburg

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Top-rated holiday rentals in Middleburg

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

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Top guest favourite
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, 252 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 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
4.96 out of 5 average rating, 109 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 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, 54 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.
Guest house 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 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
4.86 out of 5 average rating, 51 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.

Top guest favourite
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.
Guest house in Somerset
4.99 out of 5 average rating, 202 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 favourite
A modern chalet exterior features a striking combination of wood and metal, showcasing large windows that invite natural light. A small deck extends from the upper level, set against a backdrop of lush greenery. The entrance is marked by a concrete pathway leading to the main door.
Home in Somerset
4.9 out of 5 average rating, 143 reviews

Coffee with the Squirrels

New chalet only 5 minutes to city of Somerset and 5 minutes to Lake Cumberland! Cozy 1 king size bedroom with custom features throughout. Walk out on your master suite deck and have coffee with nature! Full size bathroom w custom tile. Back deck that overlooks woods and wildlife. Sometimes there is a neighbor who has a dog that barks a couple housss down, I’m sorry if it does, doesn’t happen often

Top guest favourite
The cottage's exterior features a charming red facade with a steep roof, framed by lush greenery. A pathway leads to the welcoming front door, flanked by two tall shrubs. The landscaped garden includes various plants and decorative stones, creating an inviting entrance.
Home in Harrodsburg
4.94 out of 5 average rating, 179 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.

Superhost
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.
Flat 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 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, 147 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 gravel driveway leads toward a farmstead, flanked by lush green fields. The sky is painted in warm hues of orange and pink as the sun sets in the background, creating a serene atmosphere. Fence lines guide the view, enhancing the sense of open space.
Farm stay in Campbellsville
5 out of 5 average rating, 196 reviews

The Milk Parlor on Meadow Creek Farm

Newly renovated milk parlor with beautiful views from all sides. Conveniently located minutes away from Green River Lake and Campbellsville University. Our place is perfect for writers, birdwatchers, kayakers, hikers and anyone who just needs to get away to a slower pace. We also have plenty of parking for boats and trailers.

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, 96 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