Holiday rentals in Middlesboro

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.

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.

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

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!

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. Please don't expect to fish, as the paylake is closed.

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.

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.

Pumpkin Patch

The Pumpkin Patch is a warm and cozy 2 bedroom, 1 bath bungalow with an open concept. Situated in Middlesboro, KY the only city in the USA built inside a crater. This newly renovated home is located in a quiet neighborhood at the edge of town. You'll enjoy exploring Cumberland Gap National Park, LMU, Abraham Lincoln Museum and Library and the Old Town Ghost Tours. Small pets are allowed so bring your fur baby!

The Gap Getaway - Luxury Apt Near LMU & Nat’l Park

Luxury apartment located on a main street of the historic town of Cumberland Gap, TN! Enjoy a weekend getaway at the foothills of the Appalachian Mountains. The apartment is well equipped with a full kitchen, bathroom, one bedroom, dining area, living room, washer/dryer, and a front porch with breathtaking views. Take full advantage of this home away from home with all the necessary amenities.

Rio House Retreat

Escape to The Rio House and reconnect with what matters most. With no traffic, no neighborhood noise, and no city lights, you’ll enjoy peaceful views, fresh air, and the calming sounds of nature. Relax, recharge, and celebrate special moments. Play foosball, binge your favorite shows, or simply unwind. Your quiet getaway starts here. Book today.

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.

Home away from home

Country setting with 5 minute access to town or boat launch town offers a variety of fast foods or country cooking .only 15 min. To L M U campus .this house has two covered decks ,a covered porch two living areas four bedrooms and 2 and 1/2 bathrooms