Vacation rentals in Cumberland Gap

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Top-rated vacation rentals in Cumberland Gap

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Guest favorite

Tiny home in Pineville

4.99 out of 5 average rating, 204 reviews

Nature's Zen

Nestled in a simple back to nature setting in one of Kentucky's oldest settlements (Pineville, KY) is the Nature's Zen, a tiny house retreat. If you are looking to disconnect from the hustle and bustle of life's craziness, Nature's Zen is calling your name. A quaint, restorative retreat where you can pause, take a deep breath and find refreshment for your soul and balance your life. Nature's Zen is for anyone looking for the quiet and solitude outside city limits. On FB @ Nature’s Zen Retreat

Nov 21 – 28

R1,427 ZAR per night

Guest favorite

Tiny home in Corbin

4.98 out of 5 average rating, 239 reviews

Pet Friendly True Tiny Home

This is a great stay for outdoor enthusiasts, pet lovers, or those travelling and want a homey and private place to stay for the night. The house is located in the country, but approximately 5 minutes from 1-75, 5 from Laurel Lake, 15 from Corbin, and 30 from London. Huge outdoor space which includes 1 acre private lot, large screened in porch with dinning area, a fire pit with chairs and picnic table, and fenced in back yard. Sleeps 3: upstairs loft bed is a full, downstairs is a twin.

Aug 10 – 17

R1,628 ZAR per night

Guest favorite

Guest suite in Pioneer

4.96 out of 5 average rating, 137 reviews

Kogo’s Cabin at GoodSoil Farm

The Cabin at GoodSoil Farm is the perfect solo get-a-way from it all! This cozy hand built log cabin is just right for reading, reflecting, retreating, or just resting. The Cabin sits as the centerpiece of our working mini-farm and comes replete with rocking chairs on the porch, a gurgling creek nearby, a stunning mountain view, and room to explore. Read a book, strum your guitar, prop up your feet, put on some coffee & leave your cares behind for a few days at The Cabin on GoodSoil Farm.

Jul 27 – Aug 3

R1,148 ZAR per night

Guest favorite

Cottage in Pioneer

4.99 out of 5 average rating, 199 reviews

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.

Aug 8 – 15

R1,271 ZAR per night

Guest favorite

Home in London

4.96 out of 5 average rating, 178 reviews

3 bedroom home (52) with mountain view.

Make lasting memories in this charming home! The moment you walk through the front door, you'll fall in love with the rich beautiful Mountain View! Sit back and relax on the front porch and enjoy the evening sunset after a full day of exploring the outdoors. ✅My DIGITAL guidebook is an amazing resource ✅Spectrum Wifi ✅Smart TV ✅Coffee Bar ☕️ ✅Pack n play and high chair ✅Bose Bluetooth speaker 🎼 ✅Board games 🎲 ✅Discount for long term rentals Book now and enjoy this BRAND NEW HOME.

Jan 29 – Feb 5

R1,710 ZAR per night

Guest favorite

Tiny home in Gray

4.96 out of 5 average rating, 105 reviews

Sleeping Turtle Tiny Home #1

Reconnect with nature. Sleeping Turtle Retreat and Paylake provides an unforgettable escape that is situated on a spring lake with beautiful mountain views. It is located just over 9 miles off of the I75 exit between the towns of Corbin and Barbourville. During the day you can find yourself fishing and hiking or possibly finding some local activities to do. When you're ready to relax; just sit back, make a campfire and roast some marshmallows next to your tiny home.

Nov 2 – 9

R1,487 ZAR per night

Guest favorite

Cabin in Whitley City

4.96 out of 5 average rating, 190 reviews

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.

Sep 22 – 29

R1,873 ZAR per night

Guest favorite

Cottage in Bell County

4.99 out of 5 average rating, 277 reviews

Scenic 1 BR Cabin w/ Hiking to Hensley Settlement

“Elk Creek Cottage” borders Cumberland Gap National Historical Park property--the pathway to the west, trailblazed by Daniel Boone himself! Stay and hike to Hensley Settlement or Shillalah Creek Falls, or relax with a cup of coffee on the porch surrounded by nature. Only a scenic twenty-minute drive to Middlesboro or Pineville, KY separates you from the "city." Come enjoy the peace and quiet that Elk Creek Cottage has to offer.

Oct 6 – 13

R1,984 ZAR per night

Guest favorite

Guest suite in Cumberland Gap

4.91 out of 5 average rating, 158 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.

Dec 8 – 15

R2,648 ZAR per night

Guest favorite

Home in Sneedville

4.91 out of 5 average rating, 107 reviews

Quaint Country Cottage, Nice View, hot tub!

Small cute cottage has one bedroom , one tiled bathroom and a kitchen/ living room. There’s a back porch to enjoy the ducks. On the deck is a hot tub, sauna and gas grill. Our home is also attached to the same deck. In warmer months the pool is open and heated! The hot tub is year round. . We are a small remote farm . Bring food or drive 20 min to closest restaurant. We have horses, donkeys and ducks! Fresh eggs daily.

Feb 2 – 9

R1,941 ZAR per night

Guest favorite

Cabin in Harrogate

4.91 out of 5 average rating, 364 reviews

Rustic Log Cabin on Powell River & Adventures🚣🏽‍♀️🎣

Discover a breathtaking mountain and river living experience. You’ll stay in a fully furnished log house with everything you need to make memories that will last forever! 🐟🚣🏽‍♀️🚴‍♀️We also offer kayaking, fishing, mountain biking, and camping. You can check out everything on Airbnb’s “experiences” page.

Oct 5 – 12

R3,008 ZAR per night

Guest favorite

Home in Speedwell

4.96 out of 5 average rating, 189 reviews

Guest house in the country with a beautiful view

Located in a peaceful country setting with a beautiful view from the front porch. It is conveniently located near Lincoln Memorial University, Norris Lake, and Historic Cumberland Gap. We live next door to the guest house and will be there to greet you upon arrival to answer any questions you may have.

Jan 21 – 28

R1,841 ZAR per night