Vacation rentals in Middlesboro

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Middlesboro

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

0 of 0 items showing

1 of 3 pages

Top guest favorite

A welcoming porch area is featured, with a set of steps leading up to a dark wooden door. Hanging flower pots filled with purple blooms create a vibrant contrast against the brown exterior. A small table and two chairs provide a cozy spot for relaxation.

Tiny home in Pineville

4.99 out of 5 average rating, 294 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

A peaceful creek flows through a lush, green landscape. Sunlight filters through the trees, creating shimmering reflections on the water's surface. Smooth rocks are partially submerged in the creek, adding to the natural beauty of the surrounding environment.

Cabin in Pineville

4.97 out of 5 average rating, 106 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 log cabin features a sloped roof and wooden pillars supporting the porch. Lush greenery surrounds the exterior, with a bare tree beside the entrance. A cozy stone fireplace is visible, enhancing the rustic charm of the space.

Guesthouse in Pioneer

4.96 out of 5 average rating, 180 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

Cottage in Pioneer

4.99 out of 5 average rating, 258 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 wooden dock extends into calm waters, reflecting the soft glow of the setting moon. Surrounding greenery frames the serene landscape, with distant hills barely visible in the twilight. Subtle lighting along the dock highlights the natural beauty of this lakefront location.

Apartment in Sharps Chapel

4.99 out of 5 average rating, 121 reviews

Pirate Cove - Lakefront on Norris Lake w/ dock

Lakefront - This rental is the new addition to our home. It has its own private entrance, your private great room, Master ensuite with huge walk in shower. There is a Queen size bed in the great room that would be perfect for extra guest. This part of our home is separated from our own personal living space by a sliding barn door that will be latched for your privacy. Although we will be in the main part of the home we want you to enjoy your time and enjoy Norris Lake.

Top guest favorite

A woven basket is filled with a slice of bread wrapped in plastic, two apples, and several individual servings of breakfast treats. The basket is lined with a red and white checkered paper, adding a charming touch to the presentation.

Tiny home in Gray

4.96 out of 5 average rating, 216 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 11miles off of the I75 exit. During the day you can find yourself searching out some some local activities such as Cumberland Falls, Colonel Sanders Museum and more. When you're ready to relax; just sit back, make a campfire and roast some marshmallows next to your tiny home. There's also a barbecue grill included for your summertime grilling!

Top guest favorite

A cascading waterfall flows gently over smooth rocks into a clear stream, surrounded by a natural landscape of trees and boulders. Sunlight glints off the water, revealing the varied textures of the stones beneath the surface.

Cottage in Bell County

4.98 out of 5 average rating, 326 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.

Superhost

A comfortable porch swing is situated on a covered patio, featuring a dark cushion set adorned with a patterned throw pillow. The swing is suspended by chains, surrounded by greenery, with a view of a lawn and distant trees visible in the background.

Cottage in Cumberland Gap

4.65 out of 5 average rating, 123 reviews

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Adorable, cozy cottage located on a quiet street in the historic town of Cumberland Gap, TN! Enjoy a weekend getaway at the foothills of the Appalachian Mountains along a quaint stream on the back of the property. The home is well equipped with a full kitchen, bathroom, two bedrooms, dining room, living room, and washer/dryer. Take full advantage of this home away from home in an optimal location with all the necessary amenities.

Guest favorite

An outdoor deck area is visible, featuring a seating arrangement with two dark wicker chairs and a light-colored sofa. A small area rug lies beneath the furniture. The surrounding landscape includes rolling hills and a sky filled with scattered clouds, creating a serene outdoor space.

Guest suite in Cumberland Gap

4.92 out of 5 average rating, 195 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.

Guest favorite

Home in Harrogate

4.87 out of 5 average rating, 111 reviews

Harrogate Home with Mountain View’s Dog Friendly

3 bedroom 2 bath dog friendly home. With wonderful views of the East TN mountains year round! Located 2 miles from Lincoln Memorial University. Less than 5 miles from the town of Cumberland Gap and Middlesboro, Ky. Close to Norris Lake. We take pride in ensuring cleanliness and follow strict COVID cleaning standards provided by the CDC.

Guest favorite

A kitchen countertop displays a framed artwork featuring lemons, accompanied by a small potted plant adorned with a black and white ribbon. Nearby, kitchen utensils are organized in white containers labeled 'let' and 'home.' A bottle of Italian lemon hand soap adds a touch of color.

Home in Speedwell

4.96 out of 5 average rating, 235 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.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Middlesboro vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Middlesboro

Guest favorite

A young deer is seen grazing in a grassy area, surrounded by small patches of foliage and dirt. The deer is characterized by its light brown coat, adorned with white spots, and a relaxed posture as it explores its natural setting.

Home in New Tazewell

4.95 out of 5 average rating, 20 reviews

Bear Crossing

JessecaRating, 5 stars1 week ago

We had a great stay! It was perfect for boating and easy access to the water. The cabin was cozy and private. We had one question about the alarm, and Teresa was very responsive, helpful, and friendly. Will definitely be staying here for our next boating trip.

A serene landscape is viewed from a wooden railing, showcasing layers of rolling hills blanketed by a soft layer of mist. The horizon is painted with soft hues of orange and blue, indicating the early morning sky.

Cabin in Thorn Hill

4.69 out of 5 average rating, 422 reviews

Max’s Hideout

AlbertRating, 5 stars1 month ago

We enjoyed our one night stay at Krystals. Beautiful view to say the least.

Top guest favorite

A bright balcony scene is showcased with two comfortable chairs facing a stunning view of rolling hills. Natural light fills the space, creating a serene atmosphere. A small table sits in between the chairs, inviting relaxation and enjoyment of the outdoors.

Villa in Sharps Chapel

5 out of 5 average rating, 8 reviews

Hot Tub MountainTop/Retreat 5 mins. to Norris Lake

NiekaRating, 5 stars2 days ago

From the moment I stepped into Serenity Village, I knew I was in for something special. Not a single detail was missed—everything was thoughtfully curated to create a truly peaceful and luxurious experience. The sauna and hot tub were absolutely perfect for unwinding, and the bed? Hands down the most comfortable thing I’ve ever slept in! The home itself is stunning, immaculately clean, and filled with those small, intentional touches that take a trip from great to unforgettable. You can feel the care and love that went into creating this space. I can’t thank the hosts enough for their hospitality. You both truly hit the mark with this one. I’m already planning my return—I absolutely love this home. Thank you for everything!

Top guest favorite

A charming outdoor seating area is presented with two white chairs and a bench on a stone patio. Decorative pillows add a pop of color. A small table holds a flower pot, and rolling green fields and a cloudy sky are visible in the background.

Farm stay in Speedwell

4.94 out of 5 average rating, 66 reviews

Haymaker Farm House

CarrieRating, 5 stars3 weeks ago

Our family had a wonderful stay at the Haymaker Homestead. Although I brought a lot of extra toys for our grandchildren to play with, they did not even need to get into those as they enjoyed so much free play running outside & explore the beautiful yard. We had a wonderful family get together. We loved reading about the history of your sweet home. Thank you, Miss Judy:)

Superhost

An outdoor deck is shown, featuring two black Adirondack chairs and a small table. A fire pit is positioned nearby, with twinkling lights along the railing. The scene captures a serene view of the surrounding wooded area at sunset, with distant hills silhouetted against the sky.

Home in Speedwell

4.88 out of 5 average rating, 8 reviews

TN Norris Lake cabin w/views & boat slip at Marina

ShannonRating, 5 stars7 months ago

We really enjoyed our stay in this peaceful and serene setting! The nighttime starry sky was the icing on the cake. We loved the cabin and amenities, and our hosts communicated well both before and during our stay. There are steep steps getting to the cabin, as well as into the downstairs bunk room, but it was something we could easily manage by being careful. We all enjoyed our time together in this gorgeous and secluded place; it’s a hidden gem, and we will be returning. Thank you!

Guest favorite

The front porch features a small round table and two chairs, providing a cozy space to enjoy the surrounding area. A floral arrangement is placed on the table, with scenic mountain views visible in the background under a partly cloudy sky.

Apartment in Harrogate

4.93 out of 5 average rating, 15 reviews

Mountain View Retreat - 1 1/2 mile from LMU

KristinRating, 5 stars3 weeks ago

This was a comfortable and restful place to use as a "home base" for making day trips to local attractions. We enjoyed ourselves while there. The host has provided the basics, and some extras, for cooking, relaxing, and settling in. The bed is super comfy. Some helpful amenities include: a charging station with multiple cables for different ports, great kitchen lighting, fans/lights that can be adapted for comfort, a television in three different rooms, nightlights, and full sized washer and dryer. We would be pleased to return if we were in the area again.

Top guest favorite

A winding gravel pathway leads through lush green foliage toward a serene lake. A small dock is visible, accommodating a boat, with other watercraft nearby. The peaceful setting is enhanced by trees framing the view, providing a sense of seclusion and natural beauty.

Treehouse in New Tazewell

4.98 out of 5 average rating, 53 reviews

Lakefront - Treehouse at Norris Lake

TraceyRating, 5 stars3 weeks ago

JooHee was an amazing hostess! it is very peaceful and the amenities that they provide are amazing! Hghly recommend!

Top guest favorite

A rustic cabin is positioned on a gentle slope, surrounded by trees with bare branches. The porch extends over a small stream, where water flows over smooth stones. Leaves cover the ground, adding a natural touch to the cabin's wooden structure.

Cabin in Thorn Hill

4.97 out of 5 average rating, 39 reviews

Creekside Cabin

Timothy SRating, 5 stars3 weeks ago

It’s a perfect place I’m always here visiting family and it’s a perfect place for me to just relax after visiting family!! It’s a beautiful relaxing place thank you so much an we will be back!!

Show all

Vacation rentals in Middlesboro

Top-rated vacation rentals in Middlesboro

Vacation rentals for every style

Popular amenities for Middlesboro vacation rentals

Other great vacation rentals in Middlesboro

Destinations to explore