Holiday rentals in Middleburg

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Top-rated holiday rentals in Middleburg

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Top guest favourite
An expansive deck presents scenic views of Herrington Lake, bordered by trees for a natural ambiance. Outdoor seating with a table invites relaxation, while the gentle waters below contribute to a peaceful setting.
Cottage in Harrodsburg
4.95 out of 5 average rating, 222 reviews

Paradise Cottage Enjoy lake Views and Lake Access!

Relax and enjoy! Great Herrington Lake views with lake access at Paradise Cottage! Peaceful private setting on one of the most beautiful parts of the lake. Located Mins from Multiple marinas, Bourbon trail, golf courses, Centre College/Asbury University events. 3 bedrooms, 5 beds, 2 full bathrooms, washer/dryer, newly remodeled. Sleeps 9. Includes: wi-fi, Hulu, 2 TVs, multiple decks, covered side patio, fire pit, gas grill, corn hole, kayaks and lily pad included with stay! Four parking spaces!

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, 256 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 private dock extends over the tranquil waters, surrounded by lush greenery and towering trees. Stairs lead down from a rustic path, offering direct access to the lake. The clear water reflects the surrounding natural landscape, providing a serene setting.
Cabin in Bronston
4.86 out of 5 average rating, 110 reviews

Lake front Cabin - Private dock

This cozy a-frame is located in the lakeside neighborhood of Echo Point, on Cumberland’s South Fork. Swim or fish off the dock, bring a paddle board, or drop a boat in at the nearby ramp. Relax on the deck with rock wall views and towering trees. Perfect for a couple or a small family get away. Walk to water/dock via a rustic path and stairs (it’s a steep climb!) *Not ideal for people with mobility constraints.* Stores & restaurants are 15 min drive. Dogs (2 max) welcome for add'l fee.

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, 115 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 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
4.96 out of 5 average rating, 455 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!

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, 59 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
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
4.87 out of 5 average rating, 54 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
Home in Danville
5 out of 5 average rating, 12 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 exterior of the cottage features a welcoming yellow front door and a spacious porch adorned with hanging plants. Comfortable seating is arranged on the wooden deck, surrounded by vibrant greenery and flower pots, inviting relaxation in a serene natural setting.
Home in London
4.99 out of 5 average rating, 123 reviews

The Greenhouse Cottage

The Greenhouse Cottage is a cozy little spot nestled beside two greenhouses. It’s located off a main road in a rural setting making it easily accessible. The home sits directly between London and Corbin with just a 10 minute drive to either city. The cottage is also close to three different boat ramps on Laurel River Lake and is just a skip and a hop to the Daniel Boone National Forest filled with everything outdoors.

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, 164 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 modern bedroom features a spacious, soft-colored bed adorned with multiple pillows. A bench sits at the foot of the bed, complemented by a light-colored area rug. Natural light filters through a window, highlighting the warm wood ceiling and contrasting dark accent wall.
Guest house in Somerset
4.98 out of 5 average rating, 112 reviews

Luxury Retreat w/ Hottub & Sauna

A steel framed industrial warehouse converted into an upscale suite with a modern luxury 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 King bedroom Suites, Infrared Sauna, Hot-tub and Fire-pit built for the perfect retreat.

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, 150 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