Holiday rentals in Middleburg

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Top-rated holiday rentals in Middleburg

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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, 260 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
4.97 out of 5 average rating, 116 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
4.95 out of 5 average rating, 64 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 charming two-story farmhouse features a welcoming front porch with a swing, white railings, and flower planters. The exterior is adorned with dark shutters that contrast against the white siding, framed by a lush green lawn and rolling countryside in the background.
Home in Stanford
4.97 out of 5 average rating, 161 reviews

ReJoyce Farmhouse--1920's farmhouse

Enjoy your stay at our beautiful newly renovated 1920s farm house. Situated in the gorgeous rolling central Kentucky countryside. Surrounded by working farms on the banks of beautiful unspoiled Gilberts Creek. Sit in the front porch swing listen to the sounds of a nature and a running stream. Your family and pets will enjoy the large yard and peaceful secluded setting. Close to golf, bourbon trail distilleries, Cedar Creek lake, horseback and hiking trails at Logan Hubble Park.

Guest favourite
A welcome sign is displayed on a wooden post, featuring bold white letters against a dark background. A black and white checked bow adorns the top, complementing the rustic wooden entrance of the cabin, which is crafted from light-colored planks.
Cabin in Eubank
4.88 out of 5 average rating, 32 reviews

Ruckel's Rustic Retreat Cabin B

Our Cabin B sleeps 6 with a queen bed, four twin beds. The outdoor porch features a swing, chairs, and a cozy place to listen to the Frog Symphony, go Eagle Watching, and relax. Located a short walk away is Ruckel's Paylake, and Eubank park with walking trails, disc golf course, and playground. SMOKE FREE! Your stay includes a $20 meal voucher and two fishing passes so don't forget your fishing poles! Located across the parking lot from Ruckel's Restaurant.

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, 219 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 Danville
5 out of 5 average rating, 18 reviews

Blue Moon Cottage w/ Pergola & Scenic Views

Escape to Blue Moon Cottage, a peaceful retreat in Kentucky's Knob lands just 5 miles from downtown. Surrounded by nature, this cozy getaway offers beautiful views, quiet mornings, and relaxing evenings by the fire or in the pergola. This home offers: 🌄 Scenic deck & pergola with views 🔥 Cozy fireplace 🛏️ 2 queen beds + 2 twins 🍽️ Full kitchen w/ electric range 📶 Free WiFi Perfect for families, couples, or a relaxing getaway.

Top guest favourite
The treehouse is elevated among the trees, featuring large windows that reflect the surrounding greenery. A wooden deck extends from the structure, offering outdoor seating. The area is framed by lush foliage and sunlight filtering through the leaves.
Treehouse in Campbellsville
5 out of 5 average rating, 67 reviews

New custom built treehouse

Reconnect with nature at this unforgettable escape. Green River Breeze is a new custom built 4 season treehouse. This space allows you to immerse yourself in nature while enjoying all modern amenities of home. Suspended among the trees you will fall asleep in the loft on a king size bed. You will find a fully equipped kitchen, private bathroom and small living area BUT the real beauty is the expansive deck and outdoor firepit.

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
4.91 out of 5 average rating, 175 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
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, 120 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.

Superhost
Flat in Liberty
5 out of 5 average rating, 6 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, 151 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 holiday rentals

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