Vacation rentals in Pineville

Bolton Farm CJ’S Dream House 2bed/1bath

Relax with the whole family at this peaceful place to stay. 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, plus a queen sleeper sofa, 65” tv and gas grill on deck. 5 acre field is open to explore around pond. We love hosting travel or remote workers

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.

Robertson Ridge Hideaway Cottage

Welcome to Robertson Ridge Hideaway, a modern-rustic cottage tucked away in a peaceful ridge surrounded by trees. Perfect for a business trip, cozy weekend getaway, couples’ retreat, or outdoor adventure! We also offer extra space for boats, ATVs, or off-road vehicles just a short walk away, making it easy to explore the region. You’ll be close to Cumberland Falls State Park, Cumberland Gap National Park, Laurel Lake, Pine Mountain State Park, and Union College nearby.

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.

The Bear’s Den

Take a break and unwind in the beautiful Smokey Mountains in southern Kentucky. We are situated less than 5 miles from the famous Cumberland Falls! We are close to many hiking trails and water sports. This one bedroom, one bathroom cabin boasts a full kitchen and a washer and dryer. The deck provides a peaceful view of the beautiful forest as well as a great place to relax and grill your favorite meal! An air mattress is provided for additional guests.

The Farmview Cottage

Nestled between London and Corbin, this newly built cottage offers a quiet retreat surrounded by Kentucky cattle farms. Completed in late 2025, it features a cozy cabin feel, a charming retro kitchen, two spacious bedrooms with ample closets, one half bath, and a full bath with washer and dryer. Enjoy peaceful mornings or evenings on the private covered back porch and unwind in the calm of the countryside.

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.