Holiday 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.

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.

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.

Classic Corner

Enjoy a stylish experience at this centrally-located apartment. Located in the heart of downtown Barbourville. We are within walking distance to Union College, local restaurants, and entertainment. This location has so much to offer and perfect for families with children, Union College guest and traveling professionals. We are conveniently located between Corbin and Pineville. Local attractions include Knox Sports, Cumberland Falls, Corbin Arena, Pine Mountain State Park and Cumberland Gap.

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

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.

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.

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!

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.

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.

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.

Chic Haven

Welcome to this serene and stylish 2-bedroom, 1-bath home in downtown Barbourville. Nestled in a peaceful neighborhood, the home is just a short walk from popular restaurants and local coffee shops. Guests can also take advantage of free EV charging with a NEMA 14-50 outlet (charger not provided). We look forward to hosting you!