Holiday rentals in Cumberland Gap

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Quick stats about holiday rentals in Cumberland Gap

  • Nightly prices starting at

    Cumberland Gap holiday rentals start at $155 SGD per night before taxes and fees

  • Verified guest reviews

    Over 630 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Cumberland Gap rentals

  • 4.9 Average rating

    Cumberland Gap stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated holiday rentals in Cumberland Gap

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
An inviting wooden porch is featured, adorned with potted plants and hanging ferns. Two chairs are positioned comfortably, offering a serene setting surrounded by greenery. Sunlight casts soft shadows on the porch floor, enhancing the tranquil ambiance of the space.
Cabin in Pineville
4.97 out of 5 average rating, 195 reviews

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.

Top guest favourite
A tranquil pond reflects the blue sky and scattered clouds. Lush green fields surround the water, with trees framing the edges. The serenity of the landscape invites relaxation and exploration.
Cabin in Jacksboro
4.99 out of 5 average rating, 214 reviews

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

Top guest favourite
The wooden exterior of a cozy cabin is showcased, featuring a wide front porch with sturdy railings. Sunlight illuminates the natural wood finish, and grassy areas surround the cabin, with rolling hills visible in the background under a clear blue sky.
Cabin in Harrogate
4.98 out of 5 average rating, 87 reviews

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

Guest favourite
Guest suite in Harrogate
5 out of 5 average rating, 6 reviews

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.

Guest favourite
The historic brick building is illuminated at night by warm street lights. Decorative string lights line the front, highlighting the entrance. The structure features a rounded corner and tall windows, revealing a welcoming atmosphere in the vibrant downtown area.
Guest suite in Cumberland Gap
4.91 out of 5 average rating, 222 reviews

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.

Guest favourite
Cabin in Rutledge
5 out of 5 average rating, 16 reviews

Perfect Lake Spot - "Willow Cabin" [NEW]

Enjoy a lake-life escape at the Willow Cabin! It's located on a quiet spot on the main channel of the lake, with deep water year-round – and views for miles. Note: There are 2 other cabins on the property. Guests enjoy plenty of private deck space and personal areas, for a great stay without disturbance. There are multiple fire pits, kayaks, and a large dock on site for guests to use, as well as parking onsite.

Guest favourite
Guest house in Middlesboro
4.96 out of 5 average rating, 122 reviews

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!

Guest favourite
Cabin in Pineville
4.9 out of 5 average rating, 10 reviews

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.

Guest favourite
A comfortable bedroom features a queen-size bed with a light green bedspread and vibrant orange accents. Two bedside tables hold lamps, and three framed landscape prints adorn the wall. Natural light enters through a window covered with light curtains, highlighting the room's inviting atmosphere.
Flat in Cumberland Gap
4.91 out of 5 average rating, 110 reviews

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.

Guest favourite
A well-maintained garden area features a mix of colorful flowers, including yellow lilies, alongside neat shrubbery. A stone pathway leads toward the entrance, which is framed by a brick façade and a bench. The manicured lawn provides a contrasting green backdrop.
Home in Harrogate
4.96 out of 5 average rating, 28 reviews

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.

Guest favourite
The exterior of the cottage is illuminated by warm string lights, creating a welcoming ambiance. A spacious deck is adorned with wooden beams, providing a cozy area for relaxation. Lush greenery surrounds the property, enhancing the natural setting.
Home in Tazewell
4.89 out of 5 average rating, 113 reviews

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.

Top guest favourite
Home in Tazewell
5 out of 5 average rating, 129 reviews

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!

Popular amenities for Cumberland Gap holiday rentals