Vacation rentals in Middlesboro

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Top-rated vacation rentals in Middlesboro

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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

Sep 25 – Oct 2

G$15,562 GYD 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

G$12,517 GYD 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.

Jul 30 – Aug 6

G$19,145 GYD 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.

Dec 13 – 20

G$15,011 GYD 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.

Feb 28 – Mar 7

G$18,889 GYD per night

Guest favorite

Home in Williamsburg

4.96 out of 5 average rating, 200 reviews

Cumberland Mountainside Stay 1 mile from UC Campus

Within walking distance to University of the Cumberlands, 5 minutes (2miles) off of I-75, and less than thirty minutes from the original KFC and Cumberlands Falls State Resort Park. This home is newly renovated with 2 bedrooms and 2 bathrooms, and a bonus loft bedroom for 4! Comfortable, plush living room furniture makes for great space to wind down after a day of adventuring in the beautiful Southeastern Kentucky mountains. With a fully stocked kitchen, it's like home away from home.

Dec 10 – 17

G$29,593 GYD per night

Guest favorite

Guesthouse in Williamsburg

4.89 out of 5 average rating, 430 reviews

Williamsburg Poolside Homestead

Private guest house with incredible outdoor resort feel, nature, and simple homestead life. 3 miles to University of the Cumberlands. 20 min to Cumberland Falls, home of the world's only Moonbow. *NO smoking of any kind (e-cig included) permitted anywhere on the property or the entire neighborhood. Guests violating our smoking policy are subject to a minimum $400 fee for returning the house or property to smoke-free status and agree to being charged by accepting this policy.

May 13 – 20

G$27,113 GYD per night

Guest favorite

Tiny home in Gray

4.96 out of 5 average rating, 104 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.

Jul 5 – 12

G$16,218 GYD 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

G$21,633 GYD 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 9 – 16

G$28,919 GYD 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.

Nov 17 – 24

G$21,162 GYD per night

Guest favorite

Guesthouse in Middlesboro

4.96 out of 5 average rating, 46 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!

Nov 21 – 28

G$24,453 GYD per night