Holiday rentals in Middleburg

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Top-rated holiday rentals in Middleburg

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Top guest favourite
A cozy bedroom features a full-sized bed draped in a patterned blue and white coverlet. A bedside lamp and a small table with decorative items complement the space. Natural light filters through a small window, creating a serene ambiance.
Flat in Wilmore
4.97 out of 5 average rating, 354 reviews

Basement apt. w/private entrance & kitchenette

Our full basement apartment with private entrance is modest but comfortable. Located within one mile of Asbury Seminary and University, our space is ideally suited for commuting students, out-of-town guests, or folks visiting the beautiful Bluegrass region. Our home is a 15-minute walk from the campuses and business district. We are a family of six and you will occasionally hear our boys upstairs, but as a Christian family, we strive to treat our guests as we would want to be treated. Reg. 9485

Top guest favourite
The charming bungalow features a cozy front porch with wooden accents and an inviting entrance. The exterior combines green siding and natural wood shingles, surrounded by well-maintained landscaping. A pathway leads to the door, framed by neatly trimmed bushes, offering a welcoming sight.
Bungalow in Danville
4.95 out of 5 average rating, 173 reviews

WildernessTrace BarrelProof *Hottub/firepit*

Whether you’re here for Centre College, the Bourbon Trail, or romantic getaway, you’ll find this 2 bedroom bungalow exceeds expectations. This home is conveniently located 2 1/2 blocks from Main St. so you can enjoy a nice walk to dinner to one of Danvilles restaurants. The home features a bourbon theme throughout with knick knacks from “The Mandalorian.” From barrel barrel head tables, staves, bourbon bottle lamps, and other bourbon distillery keepsakes, this house is first class throughout.

Guest favourite
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 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, 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.

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
4.97 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 favourite
A serene bedroom features a spacious bed adorned with soft linens and a decorative throw. Two windows allow natural light to fill the room, complemented by light-colored wood floors. Nightstands with lamps flank the bed, and subtle decor adds to the calming ambiance.
Home in Monticello
4.99 out of 5 average rating, 100 reviews

1/8 to Boat Launch, Spa, Fire Pit, King En-suites

Escape to Barndo Bliss, a newly built 4bd/3.5ba retreat nestled in Lake Cumberland's serene forests, just 0.8 miles from Ramsey’s Point boat ramp! Perfect for families and friends, this home features TWO luxurious King En-suites. No boat? No problem! Nearby Beaver Creek Marina offers rentals. Enjoy evenings by the large firepit surrounded by nature, perfect for s'mores, and unwind in the luxurious spa. Experience the tranquility of Lake Cumberland—book your stay at Barndo Bliss today!

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, 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 favourite
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.
Flat 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.

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, 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 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
4.98 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 favourite
Home in Harrodsburg
4.94 out of 5 average rating, 174 reviews

The Betsy Sweat Cottage.

View the cottage on YouTube listed bye 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 favourite
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.

Popular amenities for Middleburg holiday rentals

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