An aerial view of a town surrounded by mountains, with a mix of residential and commercial buildings, and a highway running through the center.

Middlesboro Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Middlesboro vacation rentals

Desk, iron/ironing board, WiFi, bed sheets

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
9.0 out of 10, Wonderful, (6 reviews)
"We enjoyed our stay. "
United States
Emily S.
The price is ￥27,764
￥56,297 total
includes taxes & fees
Jul 12 - Jul 13
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
8.0 out of 10, Very Good, (3 reviews)
"Great area to stay in "
United States
Corinna E.
The price is ￥26,960
￥55,901 total
includes taxes & fees
Jul 28 - Jul 29
Welcoming 3-bedroom house with AC in charming Middlesboro
Dining

Private bungalow close to LMU, ARH, Cumberland Gap

Private bungalow close to LMU, ARH, Cumberland Gap
Middlesboro
The price is ￥19,382
￥46,764 total
includes taxes & fees
Aug 11 - Aug 12
Private bungalow close to LMU, ARH, Cumberland Gap
Interior

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

Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
Middlesboro
7.4 out of 10, Good, (3 reviews)
"Advertised would sleep 12, yes it had beds for 12, but I guess we were to share towels , could be cleaner, food and trash under sofa cushions. Had to hunt for the WiFi password."
United States
Elita W.
The price is ￥29,335
￥61,600 total
includes taxes & fees
Aug 11 - Aug 12
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
1 bedroom, WiFi, bed sheets

Modern 20’ Travel Trailer with bunks and a queen bed

Modern 20’ Travel Trailer with bunks and a queen bed
Speedwell
The price is ￥12,611
￥22,653 total
includes taxes & fees
Jul 14 - Jul 15
Modern 20’ Travel Trailer with bunks and a queen bed
Property grounds

The Nomad on Norris Lake

The Nomad on Norris Lake
New Tazewell
The price is ￥36,378
￥61,398 total
includes taxes & fees
Jul 29 - Jul 30
The Nomad on Norris Lake
Property grounds

Wake&Lake at Norris Landing Marina-Waterfront RV Retreat with Deck + Slip Option

Wake&Lake at Norris Landing Marina-Waterfront RV Retreat with Deck + Slip Option
Tazewell
10.0 out of 10, Exceptional, (1 review)
"Everything was exceptional! The hosts are very accommodating and the camper has everything you would need to make your stay comfortable!"
United States
Morgan H.
The price is ￥24,252
￥30,781 total
includes taxes & fees
Jul 12 - Jul 13
Wake&Lake at Norris Landing Marina-Waterfront RV Retreat with Deck + Slip Option
Interior

One Bedroom Rustic Cabin

One Bedroom Rustic Cabin
Speedwell
The price is ￥7,922
￥15,755 total
includes taxes & fees
Jul 12 - Jul 13
One Bedroom Rustic Cabin
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 ￥7,437
￥20,782 total
includes taxes & fees
Jul 12 - Jul 13
Quaint Studio APT Near ATV Trails & Norris Lake
Property grounds

Charming 3-bedroom house with WiFi, AC in Pineville Kentucky

Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Pineville
10.0 out of 10, Exceptional, (8 reviews)
"clean house very beautiful, host was amazing, scenery stunning. "
United States
Evelyn B.
The price is ￥28,375
￥51,067 total
includes taxes & fees
Jul 13 - Jul 14
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Terrace/patio

Peaceful & Private! Pet-Friendly Williamsburg Home

Peaceful & Private! Pet-Friendly Williamsburg Home
Williamsburg
10.0 out of 10, Exceptional, (3 reviews)
"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 ￥14,228
￥50,263 total
includes taxes & fees
Jul 12 - Jul 13
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)
"Such a cute little apartment! It had everything we needed for our stay. "
United States
Cindy
The price is ￥18,270
￥33,777 total
includes taxes & fees
Jul 14 - Jul 15
Harrogate Hideaway - 5 Min to LMU & Nat`l Park
Exterior

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Cumberland Gap
9.4 out of 10, Exceptional, (48 reviews)
"Cozy place perfect for what we needed. "
United States
Emily N.
The price is ￥17,623
￥36,148 total
includes taxes & fees
Jul 13 - Jul 14
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Fridge, microwave, oven, stovetop

Remodeled Western Country Getaway Near Lake & Trails

Remodeled Western Country Getaway Near Lake & Trails
LaFollette
10.0 out of 10, Exceptional, (2 reviews)
"Very clean and nice apartment. Just as advertised. Had everything we needed and we were very pleased. Great place! You will not be disappointed. We will definitely be going back!"
United States
Gregory T.
The price is ￥12,773
￥30,204 total
includes taxes & fees
Jul 14 - Jul 15
Remodeled Western Country Getaway Near Lake & Trails
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, (11 reviews)
"The hosts were wonderful, very accommodating and helpful through our stay. The cabin was clean and nicely put together for a relaxing visit."
United States
Sharon W.
The price is ￥17,138
￥29,731 total
includes taxes & fees
Jul 13 - Jul 14
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
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 ￥20,372
￥49,712 total
includes taxes & fees
Jul 12 - Jul 13
Peaceful & Private! Pet-friendly Williamsburg Home
Interior

Cozy 1-bedroom cabin in marvelous Tazewell

Cozy 1-bedroom cabin in marvelous Tazewell
Tazewell
The price is ￥10,040
￥21,763 total
includes taxes & fees
Jul 12 - Jul 13
Cozy 1-bedroom cabin in marvelous Tazewell
Interior

Calm Country Oasis - Creek, ATV Trls & Norris Lake

Calm Country Oasis - Creek, ATV Trls & Norris Lake
Speedwell
9.6 out of 10, Exceptional, (24 reviews)
The price is ￥22,959
￥49,399 total
includes taxes & fees
Jul 12 - Jul 13
Calm Country Oasis - Creek, ATV Trls & Norris Lake
Exterior

Blissful Bungalow across from LMU campus

Blissful Bungalow across from LMU campus
Harrogate
9.6 out of 10, Exceptional, (39 reviews)
"Very convenient to everything we needed to do, very clean and neat"
United States
Brandi L.
The price is ￥22,474
￥41,468 total
includes taxes & fees
Aug 11 - Aug 12
Blissful Bungalow across from LMU campus
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
9.2 out of 10, Wonderful, (23 reviews)
"Nice place. Everything you need and more"
United States
Jeff L.
The price is ￥14,551
￥29,094 total
includes taxes & fees
Jul 13 - Jul 14
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
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

Econo Lodge Middlesboro

Econo Lodge Middlesboro

8/10 Good
"We came for a quick sleep. The only reason I gave the rating I did was mainly the outside of the building. It looked a little rough, worn, and in weird sections. I will say that when i made the reservation, the woman that answered was extremely helpful and very pleasant. When we arrived it was locked(lobby uses a window after hours), and it was very hard to hear the young lady at the window. This area looked worn and rough, but not terrible. I imagine the moisture from fogs and rains that roll through play a bog part in that. Our room was simple but as pictured. It had a microwave and fridge. I used to clean rooms and so I nervously checked, and pleasantly surprised that nothing was lurking anywhere. The available breakfast is a quick in and out. Hot meal was tea coffee and oatmeal. Cold was cereal, juice, milk, and all individually wrapped items. Not bad at all. Pricing was just over my $$ but you are in a smaller area, basically only hotel, and close to many things to do. I would say it was overall great. Thank you!"
Elizabeth 1-night trip
Posted 4 hours ago
Econo Lodge 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?

Lake Front 2-Bedroom Home W/ Privacy! Beautiful Views & Numerous Amenities...: This vacation home rental near Middlesboro is located on a lake and has a patio, a private yard, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

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, Cumberland Gap National Historical Park and Middlesboro Country Club 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.