Vacation rentals in Middlesboro

Find and book unique accommodation on Airbnb

Top-rated accommodation in Middlesboro

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

Guest favourite

Tiny home in Pineville

4.99 out of 5 average rating, 201 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

25 Oct – 1 Nov

$132 NZD per night
Guest favourite

Guest suite in Pioneer

4.95 out of 5 average rating, 133 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.

4–11 Oct

$128 NZD per night
Guest favourite

Tiny home in Corbin

4.98 out of 5 average rating, 235 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.

9–16 Jul

$178 NZD per night

Popular amenities for Middlesboro accommodation

Other great accommodation in Middlesboro

Guest favourite

Guest suite in Williamsburg

4.97 out of 5 average rating, 143 reviews

Creekside Adventures

21–28 Mar

$174 NZD per night
Guest favourite

Guesthouse in Jefferson City

4.99 out of 5 average rating, 135 reviews

Near Lakes, C-N, National Parks & Entertainment

14–21 Dec

$162 NZD per night
Guest favourite

Cottage in Middlesboro

4.98 out of 5 average rating, 99 reviews

2 bedroom cottage w/ fenced in back yard

13–20 Nov

$192 NZD per night
Guest favourite

Guesthouse in Middlesboro

4.95 out of 5 average rating, 44 reviews

Pumpkin Patch

17–24 Dec

$215 NZD per night
Guest favourite

Apartment in Cumberland Gap

4.93 out of 5 average rating, 60 reviews

Beautiful 2BR Apartment w/ patio above restaurant

23 Feb – 2 Mar

$232 NZD per night
Guest favourite

Home in Harrogate

4.97 out of 5 average rating, 74 reviews

Entire home. Spacious two bedroom.

24 Feb – 3 Mar

$228 NZD per night
Guest favourite

Cabin in Cumberland Gap

5.0 out of 5 average rating, 22 reviews

Cumberland Gap Cabin

10–17 Dec

$306 NZD per night
Guest favourite

Apartment in Cumberland Gap

4.93 out of 5 average rating, 40 reviews

Luxury Brooklyn St APT - Near LMU & Nat’l Park

19–26 May

$268 NZD per night
Guest favourite

Home in Harrogate

5.0 out of 5 average rating, 28 reviews

Miles’ Mini Mansion across from LMU main campus

7–14 Aug

$324 NZD per night
Superhost

Home in Harrogate

4.84 out of 5 average rating, 75 reviews

Harrogate Home with Mountain View’s Dog Friendly

20–27 Jun

$321 NZD per night
Guest favourite

Apartment in Harrogate

5.0 out of 5 average rating, 13 reviews

Harrogate, TN - 5 min. From LMU

10–17 Oct

$226 NZD per night
Superhost

Guesthouse in Rockholds

4.83 out of 5 average rating, 23 reviews

Lofty retreat

21–28 Oct

$122 NZD per night

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