Vacation rentals in Middlesborough

Morrison House Middlesboro KY

Escape to this beautiful home in Middlesboro KY nestled in the Appalachian Mountains. Built in 1944 and lovingly remodeled to keep the original character. You will enjoy quiet nights on the porch, a 65" TV with lots of streaming options, a large well stocked kitchen and comfortable beds. Minutes from LMU, the Cumberland Gap National Park, Abraham Lincoln Library, the Wilderness Trail and fishing at Canyon Creek Lake. Cook at home or enjoy some of the great restaurants in Middlesboro Welcome

Value · Family · Layout

Pine Mountain Villa on Wasiota Winds Golf Course

Relax with the whole family at this peaceful place to stay. Awesome views every where you look in this 3 bedroom/2 bath home sitting directly on the 10th green. Large rock fireplace sits in the center of the home, perfect for family gatherings. Large Den perfect for entertaining and has a antique poker table that is perfect for any card games you wish to play. There is a screened in back porch complete with porch swing. Sitting area in front with 2 Adirondack chairs to enjoy the mountain views.

Location · Family · Comfort

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.

Value · Family · Kitchen

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

Location · Value · Bathroom

Pump Springs Farm

Cozy Cabin at Pump Springs Farm, Nestled in East Tennessee’s foothills, our 1B1B guest cabin at Pump Springs Farm offers rustic charm & modern comfort. Near LMU, it’s perfect for students, families, or if you're passing through. Enjoy HDTV, standing Desk, Free Fiber Wi-Fi, & mountain views with 🐮s. Hike Cumberland Gap trails! Visit the National park! Canoe Powell River! Pet-friendly. Heat/AC, Washer/Dryer, Kitchen, King, Queen+twin pullouts, pack&play, shared driveway

Value · Family · Hiking

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.

Location · Value · Hospitality

Secluded A-Frame Retreat on Private Pond

Escape to our peaceful luxury log cabin nestled in the mountains of Kentucky. This spacious A-frame retreat overlooks a private pond and offers the perfect blend of charm and comfort. Relax on the wraparound porch, enjoy morning coffee surrounded by nature, or unwind inside beneath soaring wood ceilings. The cabin features warm lodge-style interiors, a full kitchen, Wi-Fi, and beautiful views from every angle.

Location · Outdoor spaces · View

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.

Family · Location · Bathroom

Mountainview Manor

Escape to Mountanview Manor, a peaceful mountain retreat with 3 spacious bedrooms, 2 full baths, and a large, fully equipped kitchen. Enjoy stunning mountain views from the outdoor space. Minutes from Lincoln Memorial University, Cumberland Gap National Historical Park, and the Powell River for biking, hiking, and kayaking. Relax, recharge, and take in the beauty of the mountains.

Family · Location · Bathroom

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.

Family · Value · Parks

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.

Value · Location · Walkability

The White House

Relax with the whole family at this peaceful place to stay. A short 5 mile drive off of Highway 25E, this home away from home will have you conveniently located 10-15 minutes from Clinch River and Norris Lake. LMU is 22 miles - 29 minutes away!

Location · Family · Sleep quality