Middlesboro Vacation Rentals

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Middlesboro vacation rentals

Dining

Private bungalow close to LMU, ARH, Cumberland Gap

Private bungalow close to LMU, ARH, Cumberland Gap
Middlesboro
The price is ￥18,687
￥44,814 total
includes taxes & fees
May 20 - May 21
Private bungalow close to LMU, ARH, Cumberland Gap
Exterior detail

Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Middlesboro
9.2 out of 10, Wonderful, (5 reviews)
"We enjoyed our stay. "
United States
Emily S.
The price is ￥27,259
￥55,799 total
includes taxes & fees
May 20 - May 21
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Exterior

Welcoming 3-bedroom house with AC in charming Middlesboro

Welcoming 3-bedroom house with AC in charming Middlesboro
Middlesboro
7.0 out of 10, Good, (2 reviews)
"Great area to stay in "
United States
Corinna E.
The price is ￥26,470
￥54,710 total
includes taxes & fees
May 20 - May 21
Welcoming 3-bedroom house with AC in charming Middlesboro
Interior

Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU

Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
Middlesboro
8.0 out of 10, Very Good, (2 reviews)
"Clean"
United States
Phineas S.
The price is ￥28,116
￥58,459 total
includes taxes & fees
Jun 2 - Jun 3
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
Miscellaneous

RV/Camper Sites. No Electric

RV/Camper Sites. No Electric
Speedwell
The price is ￥4,603
￥10,124 total
includes taxes & fees
May 20 - May 21
RV/Camper Sites. No Electric
Fridge, microwave, oven, stovetop

Outback Behind the Barn

Outback Behind the Barn
Ewing
The price is ￥16,191
￥21,696 total
includes taxes & fees
May 20 - May 21
Outback Behind the Barn
Miscellaneous

The Nomad on Norris Lake

The Nomad on Norris Lake
New Tazewell
The price is ￥35,717
￥60,123 total
includes taxes & fees
May 27 - May 28
The Nomad on Norris Lake
1 bedroom, free WiFi, bed sheets

Quaint Studio APT Near ATV Trails & Norris Lake

Quaint Studio APT Near ATV Trails & Norris Lake
LaFollette
9.6 out of 10, Exceptional, (11 reviews)
"Check in was very easy amazing little place. Loved the mornings going out to the porch and hearing the birds chirping. Definitely coming back and staying again "
United States
Melisza
The price is ￥7,778
￥20,947 total
includes taxes & fees
May 31 - Jun 1
Quaint Studio APT Near ATV Trails & Norris Lake
Fridge, microwave, oven, stovetop

Updated Apt in Country - ATV Trls & Norris Lake

Updated Apt in Country - ATV Trls & Norris Lake
LaFollette
9.6 out of 10, Exceptional, (5 reviews)
"Fantastic stay! The place was clean, comfortable, and exactly as described. They were an excellent host—responsive and helpful. We felt right at home and would absolutely stay here again. Highly recommend!"
United States
madison a.
The price is ￥9,366
￥24,576 total
includes taxes & fees
May 25 - May 26
Updated Apt in Country - ATV Trls & Norris Lake
Terrace/patio

Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina

Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
Speedwell
9.4 out of 10, Exceptional, (20 reviews)
"Cute and cozy! Perfect place for us to use as a home base while in town visiting family. Lots of attention to the details, kitchen facilities are up to date and super clean. Already looking forward to booking again!"
United States
Lynette M.
The price is ￥14,287
￥28,566 total
includes taxes & fees
May 20 - May 21
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
House (2 Bedrooms) | Front of property

Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home
3.0 star property
Williamsburg
The price is ￥15,557
￥48,726 total
includes taxes & fees
May 20 - May 21
Peaceful & Private! Pet-friendly Williamsburg Home
Terrace/patio

Peaceful & Private! Pet-Friendly Williamsburg Home

Peaceful & Private! Pet-Friendly Williamsburg Home
Williamsburg
10.0 out of 10, Exceptional, (1 review)
"Beautiful peaceful setting, great views! Host was very nice and helpful! Home was very clean and comfortable. Pet friendly, and kid friendly :)Highly recommend!"
United States
Alicia M.
The price is ￥13,969
￥48,766 total
includes taxes & fees
May 20 - May 21
Peaceful & Private! Pet-Friendly Williamsburg Home
Fridge, microwave, oven, stovetop

Harrogate Hideaway - 5 Min to LMU & Nat`l Park

Harrogate Hideaway - 5 Min to LMU & Nat`l Park
Harrogate
9.8 out of 10, Exceptional, (16 reviews)
"Harrogate Hideaway was a very clean and cute place to stay. We really enjoyed our time here. Our host Ciara was great!"
United States
Carla P.
The price is ￥15,724
￥30,594 total
includes taxes & fees
May 21 - May 22
Harrogate Hideaway - 5 Min to LMU & Nat`l Park
Smart TV, fireplace

Beautiful Loft in the Woods

Beautiful Loft in the Woods
Harlan
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful setting. Incredible space well laid out. Owner was very engaging. "
United States
Fred
The price is ￥19,049
￥40,423 total
includes taxes & fees
Jun 8 - Jun 9
Beautiful Loft in the Woods
TV, fireplace, books

Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg

Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg
Williamsburg
The price is ￥14,763
￥54,273 total
includes taxes & fees
May 20 - May 21
Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg
Fridge, microwave, oven, stovetop

Remodeled Western Country Getaway Near Lake & Trails

Remodeled Western Country Getaway Near Lake & Trails
LaFollette
The price is ￥12,540
￥28,203 total
includes taxes & fees
May 21 - May 22
Remodeled Western Country Getaway Near Lake & Trails
Exterior

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Cumberland Gap
9.2 out of 10, Wonderful, (46 reviews)
"Cozy place perfect for what we needed. "
United States
Emily N.
The price is ￥16,668
￥34,772 total
includes taxes & fees
May 27 - May 28
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Terrace/patio

Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!

Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
Tazewell
9.2 out of 10, Wonderful, (9 reviews)
"We had a great stay. Everything was perfect. Would recommend this place to anyone visiting the area. "
United States
Tim D.
The price is ￥17,461
￥29,903 total
includes taxes & fees
May 26 - May 27
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
Exterior

Robertson Ridge Hideaway Cottage

Robertson Ridge Hideaway Cottage
Hinkle
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful place "
United States
Isaac L.
The price is ￥17,858
￥23,188 total
includes taxes & fees
May 21 - May 22
Robertson Ridge Hideaway Cottage
Exterior

Blissful Bungalow across from LMU campus

Blissful Bungalow across from LMU campus
Harrogate
9.6 out of 10, Exceptional, (35 reviews)
"Very convenient to everything we needed to do, very clean and neat"
United States
Brandi L.
The price is ￥17,303
￥35,368 total
includes taxes & fees
May 26 - May 27
Blissful Bungalow across from LMU campus
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Middlesboro Hotel Reviews

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

10/10 Excellent
"It was good"
Rines 2-night trip
Posted 8 hours ago
Sleep Inn & Suites Middlesboro

Find out more about Middlesboro

Search for holiday rentals in Middlesboro on Expedia! You can easily find your home rentals, villas, holiday apartments in Middlesboro using one of the methods below:

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Look no further and take a look at our great range of rental properties in Middlesboro!

Frequently asked questions

Are there vacation rentals in Middlesboro?

Yes, we offer vacation rentals close to the most popular sights in Middlesboro, or you can choose a secluded option if you'd like a relaxing place to stay. Nature enthusiasts will enjoy the mountain landscape in Middlesboro. Make sure you have time to check out the churches while you're in the area.

What's the top vacation rental that Middlesboro has to offer?

Beautiful Norris Lake WATERFRONT. Near Flat Hollow Marina. Private dock.: This vacation home rental near Middlesboro is located on a lake and has a balcony, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals are there in Middlesboro?

With 6 Expedia vacation rentals, you're sure to find just the right place for your Middlesboro stay.

What’s there to see and do in Middlesboro?

Cultural attractions include Bell County Historical Society Museum, whereas Kentucky Ridge State Forest is a spot to enjoy nature. While here, Middlesboro Mall and Cumberland Gap National Historical Park are other places worth a visit.

What’s a vacation rental in Middlesboro like?

Vacation rentals are private properties you can stay in for short or long periods in Middlesboro. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for small groups.