Middlesboro Vacation Rentals

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Our top choices for Middlesboro vacation rentals

4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,

4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
Middlesboro
10.0 out of 10, Exceptional, (23 reviews)
"Very nice and extra clean great time"
United States
Johnny C.
The price is CA $163
CA $314 total
includes taxes & fees
Feb 18 - Feb 19
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,

3-bedroom home away from home in Middesboro. A family friendly environment.

3-bedroom home away from home in Middesboro. A family friendly environment.
Middlesboro
The price is CA $140
CA $222 total
includes taxes & fees
Feb 9 - Feb 10
3-bedroom home away from home in Middesboro. A family friendly environment.

3-bedroom bungalow in the heart of Crater City, near airport LMU & hiking trails

3-bedroom bungalow in the heart of Crater City, near airport LMU & hiking trails
Middlesboro
The price is CA $174
CA $391 total
includes taxes & fees
Feb 9 - Feb 10
3-bedroom bungalow in the heart of Crater City, near airport LMU & hiking trails

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 CA $239
CA $507 total
includes taxes & fees
Feb 8 - Feb 9
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

Welcoming 3-bedroom house with AC in charming Middlesboro

Welcoming 3-bedroom house with AC in charming Middlesboro
Middlesboro
The price is CA $184
CA $401 total
includes taxes & fees
Feb 9 - Feb 10
Welcoming 3-bedroom house with AC in charming Middlesboro

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

Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
Middlesboro
10.0 out of 10, Exceptional, (1 review)
"Clean"
United States
Phineas S.
The price is CA $505
CA $804 total
includes taxes & fees
Feb 17 - Feb 18
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU

Modern 20’ Travel Trailer with bunks and a queen bed

Modern 20’ Travel Trailer with bunks and a queen bed
Speedwell
The price is CA $86
CA $169 total
includes taxes & fees
Feb 9 - Feb 10
Modern 20’ Travel Trailer with bunks and a queen bed

Outback Behind the Barn

Outback Behind the Barn
Ewing
The price is CA $139
CA $187 total
includes taxes & fees
Feb 13 - Feb 14
Outback Behind the Barn

RV/Camper Sites. No Electric

RV/Camper Sites. No Electric
Speedwell
The price is CA $45
CA $93 total
includes taxes & fees
Feb 9 - Feb 10
RV/Camper Sites. No Electric

Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home
3.0 star property
Williamsburg
The price is CA $134
CA $420 total
includes taxes & fees
Feb 8 - Feb 9
Peaceful & Private! Pet-friendly Williamsburg Home

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, (44 reviews)
"Great location. Easy walk to town and close to hiking areas. Highly recommend. "
United States
Linda O.
The price is CA $135
CA $290 total
includes taxes & fees
Feb 17 - Feb 18
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

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, (8 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 CA $137
CA $266 total
includes taxes & fees
Feb 16 - Feb 17
Harrogate Hideaway - 5 Min to LMU & Nat`l Park

Calm Country Oasis - Creek, ATV Trls & Norris Lake

Calm Country Oasis - Creek, ATV Trls & Norris Lake
Speedwell
9.4 out of 10, Exceptional, (22 reviews)
"We had a wonderful weekend:)"
United States
Bobbi F.
The price is CA $150
CA $360 total
includes taxes & fees
Feb 8 - Feb 9
Calm Country Oasis - Creek, ATV Trls & Norris Lake

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

Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
Tazewell
10.0 out of 10, Exceptional, (6 reviews)
"Everything was clean and felt like home.host was really nice and I will definitely be staying again."
United States
Nicholas H.
The price is CA $133
CA $238 total
includes taxes & fees
Feb 9 - Feb 10
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!

Harrogate Home Mountain View’s Dog Friendly

Harrogate Home Mountain View’s Dog Friendly
Harrogate
10.0 out of 10, Exceptional, (22 reviews)
"Great location with friendly neighbors!"
United States
Evan C.
The price is CA $147
CA $323 total
includes taxes & fees
Feb 9 - Feb 10
Harrogate Home Mountain View’s Dog Friendly

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 CA $164
CA $353 total
includes taxes & fees
Feb 9 - Feb 10
Beautiful Loft in the Woods

Quaint Studio APT Near ATV Trails & Norris Lake

Quaint Studio APT Near ATV Trails & Norris Lake
LaFollette
9.4 out of 10, Exceptional, (10 reviews)
"The place was very clean and cozy. Quite area. Was a great stay for the weekend trip. "
United States
Mary
The price is CA $63
CA $176 total
includes taxes & fees
Feb 8 - Feb 9
Quaint Studio APT Near ATV Trails & Norris Lake

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

Luxury Brooklyn St APT - Near LMU & Nat’l Park
Cumberland Gap
9.6 out of 10, Exceptional, (25 reviews)
"This place was just as described and perfect for our stay!"
United States
Melissa M.
The price is CA $134
CA $273 total
includes taxes & fees
Feb 8 - Feb 9
Luxury Brooklyn St APT - Near LMU & Nat’l Park

Blissful Bungalow across from LMU campus

Blissful Bungalow across from LMU campus
Harrogate
9.6 out of 10, Exceptional, (32 reviews)
"Cozy feel and relaxing. "
United States
Cynthia
The price is CA $150
CA $308 total
includes taxes & fees
Feb 8 - Feb 9
Blissful Bungalow across from LMU campus

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, (19 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 CA $98
CA $218 total
includes taxes & fees
Feb 16 - Feb 17
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

Find out more about Middlesboro

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Middlesboro. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Secluded No Wake Cove - Private Covered Dock-Screened Porch-Kayaks: This vacation home near Middlesboro offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. 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 7 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.