Holiday houses in Cumberland Gap

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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
A serene pond reflects the clear blue sky and surrounding greenery. Rolling hills and a field are visible in the background, creating a peaceful rural landscape. Trees line the edge of the pond, enhancing the natural setting.
Cabin in Jacksboro
5 out of 5 average rating, 101 reviews

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

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, 187 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.

Guest favourite
Large windows frame the serene view of surrounding trees, allowing natural light to fill the space. A spacious bed is positioned in the foreground, offering a comfortable place to relax while enjoying the peaceful greenery just outside.
Tiny home in Corbin
4.95 out of 5 average rating, 322 reviews

Cozy Cumberland Cabin

Tiny Cabin on the edge of Daniel Boone National Forest. Ten minutes to Cumberland Falls, fifteen minutes to Grove Marina at Laurel Lake, and ten minutes to hiking trails. Located on 5.5 acres, this beautiful wooded land can offer privacy or room to bring some friends. Designed to be simple, attractive, stylish, and clean, with large windows to bring the outside in for a relaxing environment. Large porch to escape the mosquitoes, fire pit for use to keep warm, and plenty of space to explore.

Top Guest favourite
A welcoming living area features a sleek futon and a woven chair, arranged on a patterned area rug. Natural light fills the space through sliding glass doors, which lead to an outdoor deck, framed by lush greenery visible outside.
Guesthouse in Powell
4.99 out of 5 average rating, 284 reviews

Private Guesthouse—serene & conveniently located!

Surrounded by woods, this peaceful studio guesthouse provides a retreat-like setting close to our vibrant downtown. The private quarters feature granite countertops, fully-stocked kitchen, separate entrance, comfy bed, sun-filled rooms & a lovely, outdoor seating area to enjoy the quiet. *4 min to Kroger grocery & restaurants *6 min to Tennova North Hospital—perfect for travel nurses! *12 min to downtown *16 min to UT's Neyland Stadium & Thompson Boling Arena *1 hr to the Smoky Mountains

Top Guest favourite
A modern, two-story building is showcased against a clear blue sky. The exterior features a mix of white siding and wooden accents. A wooden pergola extends over a patio at the entrance, providing a shaded outdoor space. Large windows enhance natural light throughout.
Farm stay in Jefferson City
4.95 out of 5 average rating, 124 reviews

2AS Luxury Barndo Europe Style with Highland Cows

Welcome to a premium East Tennessee experience, where farm life charm meets modern European luxury. This high-end apartment offers the perfect retreat for those seeking comfort, sophistication, & a touch of countryside tranquility. Nestled on a scenic farm, this space is ideal for couples, solo travelers, & business looking for a stylish & peaceful getaway. All our unique listings airbnb.com/p/cedarpondfarms Only 25 miles from the UT Knoxville & 3 Miles from Carson-Newman University.

Guest favourite
A serene sunset is displayed over the lake, with vibrant hues of pink and purple reflected on the water's surface. Silhouettes of trees and distant hills frame the tranquil scene, creating a peaceful atmosphere.
Home in Newport
4.95 out of 5 average rating, 121 reviews

Lake View Cottage on Douglas Lake/ lake access

Totally remodeled home with gorgeous lake views and stunning sunsets along with lake access. Newly remodeled and freshly painted with all new appliances, new mattresses and bedding, new wrap around deck, new fire pit, new flooring, and lots of outdoor furniture to enjoy the views of the lake and amazing sunsets. The home is nestled in a family oriented campground with wildlife close by. *Note* typically between September and March the lake levels are down.

Top Guest favourite
An aerial view captures the unique repurposed silo with a circular design and a red tin roof. Surrounding greenery enhances the setting, while a hot tub and patio area with dining furniture are visible. Neatly arranged landscaping features small trees and decorative stones.
Farm stay in Sneedville
4.98 out of 5 average rating, 214 reviews

Red Bin

This memorable place is anything but ordinary. This repurposed Silo is located on a working farm. Featuring stunning craftsmanship and lots of relaxing amenities for up to two guest. The property includes stunning mountain views, hiking trails, a small creek for fishing, a luxurious spa, fire pit, and patio. AND, if you love the fall, the leaves can be spectacular here! The best is you do not have to fight the crowds in Smoky Mountain tourist traps!

Guest favourite
Guest suite in Cumberland Gap
4.91 out of 5 average rating, 221 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
Guesthouse in Middlesboro
4.96 out of 5 average rating, 120 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
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.
Apartment in Cumberland Gap
4.91 out of 5 average rating, 108 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
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
4.91 out of 5 average rating, 108 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.

Guest favourite
The front of the house features a brick facade with large windows and dual planters adorned with decorative elements. A manicured lawn leads to the entrance, offering a welcoming sight with low shrubs and green foliage framing the pathway.
Home in Harrogate
4.9 out of 5 average rating, 138 reviews

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.

Popular amenities for Cumberland Gap holiday rentals

Quick stats about holiday rentals in Cumberland Gap

  • Nightly prices starting at

    Cumberland Gap holiday rentals start at $170 AUD 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!