Vacation rentals in Middlesborough

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Top-rated vacation rentals in Middlesborough

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Top guest favorite

A cozy tiny house retreat features wooden siding with vibrant blue accents. Two large windows on either side of the entrance invite natural light. A set of five wooden steps leads to a welcoming front porch, which includes two wooden chairs, surrounded by lush greenery.

Tiny home in Pineville

4.99 out of 5 average rating, 314 reviews

Nature's Zen

Nestled in a simple back to nature setting in one of Kentucky's oldest settlements (Pineville, KY) is the Nature's Zen, a tiny house retreat. If you are looking to disconnect from the hustle and bustle of life's craziness, Nature's Zen is calling your name. A quaint, restorative retreat where you can pause, take a deep breath and find refreshment for your soul and balance your life. Nature's Zen is for anyone looking for the quiet and solitude outside city limits. On FB @ Nature’s Zen Retreat

Top guest favorite

An inviting wooden porch is featured, adorned with potted plants and hanging ferns. Two chairs are positioned comfortably, offering a serene setting surrounded by greenery. Sunlight casts soft shadows on the porch floor, enhancing the tranquil ambiance of the space.

Cabin in Pineville

4.98 out of 5 average rating, 128 reviews

Outdoor Lover's Creekside Cabin (dog friendly)

Enjoy all the scenery of Bell county in this creekside cabin. Whether you prefer to hike, fish, ride sxs, or just enjoy scenery, we have it all. 3 min from Pine Mtn State Park and Wasioto Winds Golf Course, 7 min to downtown Pineville, 20 min to Cumberland Gap National Park. Kingdom Come State Park and Cumberland Falls are an hour drive. Load up your sxs or atv and ride one of the many trails right from the driveway! Black Mountain Off Road Park and Tackett Creek are also about an hour away.

Top guest favorite

The kitchen features modern gray cabinets and a wooden table set for two. A coffee maker and kettle are visible next to a window, while a white stove and clock adorn the wall. Soft lighting creates a welcoming space in the log cabin's rustic setting.

Guesthouse in Pioneer

4.96 out of 5 average rating, 196 reviews

Appalachian Mountain Log Cabin (Private Retreat)

The Cabin at GoodSoil Farm is the perfect solo get-a-way from it all! This cozy hand built log cabin is just right for reading, reflecting, retreating, or just resting. The Cabin sits as the centerpiece of our working mini-farm and comes replete with rocking chairs on the porch, a gurgling creek nearby, a stunning mountain view, and room to explore. Read a book, strum your guitar, prop up your feet, put on some coffee & leave your cares behind for a few days at The Cabin on GoodSoil Farm.

Top guest favorite

A tiny home features a bright orange facade with a welcoming porch. A white door is flanked by a window, and steps lead up to the entrance. Surrounding grassy spaces are dotted with trees, and a fire pit is visible nearby.

Tiny home in Gray

4.96 out of 5 average rating, 240 reviews

Sleeping Turtle Tiny Home

We provide an escape that is situated near a spring lake with beautiful mountain views. It is located just over 11 miles off of the I75 exit. During the day you can find yourself searching out some local activities such as Cumberland Falls, Colonel Sanders Museum... When you're ready to relax; just sit back, make a campfire to roast marshmallows or fire up the barbecue grill! This is a former paylake and no longer used for fishing except when private events have booked the entire property.

Top guest favorite

A cozy sitting area is featured with two swivel rockers positioned near a wooden shelf and kitchenette. Natural light enters through large windows, and soft lighting is provided by string lights overhead. A decorative rug lies beneath the chairs, enhancing the inviting space.

Cottage in Pioneer

4.99 out of 5 average rating, 264 reviews

The Ambleside Cottage

The Ambleside Cottage offers full privacy for a single or a couple looking for a serene getaway surrounded by the beauty of the Appalachian mountains. This magical cabin is conveniently located for travelers, yet Ambleside feel like a remote retreat nestled in the woods above Elk Fork Creek. The Cottage is an adorable tiny house, offering 500 square feet of living space with a kitchenette, a sitting area, and a bathroom with a shower. The queen-size bed is upstairs in the sleeping loft.

Top guest favorite

A tranquil pond reflects the blue sky and scattered clouds. Lush green fields surround the water, with trees framing the edges. The serenity of the landscape invites relaxation and exploration.

Cabin in Jacksboro

4.99 out of 5 average rating, 152 reviews

Bolton Farm Jackie’s Jewel 2 bd/1 bath

Farm experience/relax and enjoy our 15 acre little piece of heaven.Sit on the deck overlook the fish pond,watch the mini animals play in the field. View goats, mini ponies/donkeys. free gated secure parking for your atv/boat trailer. Full stocked kitchen,tile walk in shower, washer/dryer, Qn bed, queen sleeper sofa, 65” tv and gas grill on deck. 5 acre field is open to explore around pond. We love hosting please inquire about discounts on extended stays for travel nurses or remote workers

Top guest favorite

A dining area is illuminated by natural light, featuring a glass-top table surrounded by four white chairs with teal cushions. Two framed botanical prints adorn the wall above, while a small coffee station with a retro coffee maker is positioned beside a cabinet against the wall.

Farm stay in LaFollette

4.97 out of 5 average rating, 106 reviews

Funky Farmhouse [Fenced in yard w/cows] 4 Marinas!

Come and get the full farm experience! Nestled on a hill overlooking our family Farm and 30 head of cattle the views and county scenery wont disappoint and with a full fenced in yard the whole family including pets and children can play more safely. The Funky Farmhouse originally built in the 1960s by my Great Grandfather has gotten a complete renovation including city water and a brand new kitchen with lots of appliances. Located minutes from Marinas and trailheads = more time for fun!

Guest favorite

A spacious game room is highlighted by a red felt pool table, positioned near large windows that allow natural light. A stone fireplace adds warmth to the room, while bar stools and a dark wood couch provide comfortable seating options for relaxation.

Guest suite in Williamsburg

4.96 out of 5 average rating, 213 reviews

Creekside Adventures

Make some memories at this unique and family-friendly place. Our guest suite is very spacious and open. Many of our guest have let us know how inviting and relaxing it is to stay in. We also have a creek where our children use to play when they were little. Kids can easily play in it when the weather is nice but please be careful on the walls and stones. We also have a pool area that is available for swimming during late May through early September. We do not allow pets. No Parties

Top guest favorite

The exterior of Elk Creek Cottage is showcased, featuring a wooden facade surrounded by trees in autumn hues. A gravel driveway leads to the steps, and a spacious porch is visible with seating areas under an overhang, inviting guests to enjoy the natural surroundings.

Cottage in Bell County

4.99 out of 5 average rating, 335 reviews

Scenic 1 BR Cabin w/ Hiking to Hensley Settlement

“Elk Creek Cottage” borders Cumberland Gap National Historical Park property--the pathway to the west, trailblazed by Daniel Boone himself! Stay and hike to Hensley Settlement or Shillalah Creek Falls, or relax with a cup of coffee on the porch surrounded by nature. Only a scenic twenty-minute drive to Middlesboro or Pineville, KY separates you from the "city." Come enjoy the peace and quiet that Elk Creek Cottage has to offer.

Guest favorite

A warm living area features rich cherry wood flooring and exposed brick walls. Comfortable seating is arranged around a well-lit space, with a stylish coffee table and decorative accessories present. A blend of antique and modern furnishings showcases the historic character of the property.

Guest suite in Cumberland Gap

4.91 out of 5 average rating, 203 reviews

The Inn over Angelo's

Detailed with antique mahogany trim, cherry wood flooring, hand-carved fireplace mantles and housed in a building built in 1890, this historic property has been many things over time. The Inn occupies 1,100 sf over Angelo's in the Gap, an Italian cuisine restaurant with recipes decades old. The Vault Tap House and Pub, showcasing 29 craft and domestic beers, features the original town bank vault, now a walk-in cooler.

Top guest favorite

A pair of glass double doors is framed in white, leading to the interior space. The doors feature vertical blinds for privacy. A welcome mat is positioned in front, with a warm light fixture illuminating the area, highlighting the brick exterior.

Apartment in Morristown

4.93 out of 5 average rating, 121 reviews

A Stay On Brentwood

This location is in the heart of Morristown with a variety of restaurants and quick access to interstate 40 and interstate 81. With the Néw interstate access, the drive to pigeon Forge is about 45 but could be longer depending on traffic. Guest are encouraged to allow more time during peak season ( March- December ) This listing is NOT a good fit for small or toddler children because of the kitchenette and fireplace.

Guest favorite

A guest house is nestled among evergreen trees, with a welcoming porch framed by lush greenery. The front porch is visible, providing a cozy setting that invites relaxation amidst the peaceful country landscape.

Home in Speedwell

4.96 out of 5 average rating, 243 reviews

Guest house in the country with a beautiful view

Located in a peaceful country setting with a beautiful view from the front porch. It is conveniently located near Lincoln Memorial University, Norris Lake, and Historic Cumberland Gap. We live next door to the guest house and will be there to greet you upon arrival to answer any questions you may have.