Vacation rentals in Pineville

The Paddock | Romantic Stargazing Cabin

Escape to a private romantic cabin tucked away on a quiet hilltop- with a spa-style shower & cozy fireplace. Designed so you don’t have to think about a thing, everything is set up for comfort and relaxation from the moment you arrive. Step outside in the evening and enjoy a stargazing experience from your private setting, complete with a telescope for viewing the night sky—perfect for unwinding under a sky full of stars. 15–20 minutes from I-75 tucked away enough to feel like a true escape.

Location · Access · Outdoor spaces

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 · Bathroom

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.

Location · Value · Pets

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.

Value · Location · Indoor spaces

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

Family · Location · Backyard

The Luxurious Lustron House

Welcome to the beautiful and updated Lustron House! Located in downtown Barbourville, this house has so much to offer! Perfect for families with children, honeymooners, guests of Union College, traveling professionals or those just wanting to learn more about the beautiful Appalachian region. Within walking distance to restaurants, shopping and Union College. A short drive to Lexington or Knoxville and many outdoor attractions like Cumberland Falls and historic Cumberland Gap.

Family · Location · Outdoor spaces

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

Family · Location · View

Bear Lodge in the Gap

Welcome to Bear Lodge where luxury and history meet at the best location in the Cumberland Gap area. Stay in a historic log framed cabin built in the early 1900s that boasts charm and character with a new modern update in 2026. Sitting at the base of the Cumberland Gap National Forest this home has 5 acres adjoining the park with a private hiking road up the mountain. Its ideal central location is less than 1 mile to LMU, Middlesboro and the town of Cumberland Gap.

Location · Hiking · Comfort

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.

Value · Location · Outdoor spaces

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 · Nearby · Decor

Cozy Cottage

Close to down town Pineville, LMU campus, Pine Mountain State Park, Bell Theater, Cumberland Gap National Park. This centrally located cottage is just 5 minutes from downtown Pineville & Wasioto Winds Golf Course. 7 minute drive to Pine Mountain State Park, 15 min to Middlesboro, 20 min to Lincoln Memorial University, 13 min drive to Cumberland Gap National Park, 30 min to Harlan and 60 min to Lynch.

Value · Family · Cleanliness

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.

Value · Location · Accuracy