Middlesboro Vacation Rentals

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Check prices for these dates

In two weeks
Apr 17 - Apr 19
In two months
May 29 - May 31
In three months
Jun 26 - Jun 28
In four months
Jul 24 - Jul 26

Our top choices for Middlesboro vacation rentals

2 bedrooms, iron/ironing board, free WiFi, bed sheets

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, (29 reviews)
"We had a lovely stay. The host was easy to contact and very responsive. The house itself suited our needs perfectly. The small touches like the s’mores kit and goodies left was a nice bonus. "
United States
Brian D.
The price is ￥18,889
￥36,397 total
includes taxes & fees
Apr 6 - Apr 7
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
Interior

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 ￥29,314
￥58,627 total
includes taxes & fees
Apr 7 - Apr 8
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
3 bedrooms, desk, iron/ironing board, travel crib

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 ￥27,257
￥53,743 total
includes taxes & fees
Apr 2 - Apr 3
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
The price is ￥26,468
￥53,051 total
includes taxes & fees
Apr 5 - Apr 6
Welcoming 3-bedroom house with AC in charming Middlesboro
Exterior detail

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 ￥18,686
￥43,264 total
includes taxes & fees
Apr 2 - Apr 3
3-bedroom bungalow in the heart of Crater City, near airport LMU & hiking trails
Fridge, microwave, oven, stovetop

Outback Behind the Barn

Outback Behind the Barn
Ewing
The price is ￥16,190
￥21,695 total
includes taxes & fees
Apr 2 - Apr 3
Outback Behind the Barn
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 ￥9,841
￥19,389 total
includes taxes & fees
May 1 - May 2
Modern 20’ Travel Trailer with bunks and a queen bed
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)
"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 ￥15,079
￥27,228 total
includes taxes & fees
Apr 2 - Apr 3
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
Interior

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)
"A very clean and comfortable home, close to where we wanted to be. Responsive host."
United States
David M.
The price is ￥17,302
￥41,346 total
includes taxes & fees
Apr 5 - Apr 6
Calm Country Oasis - Creek, ATV Trls & Norris Lake
Fridge, microwave, oven, stovetop

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

Harrogate Hideaway - 5 Min to LMU & Nat`l Park
Harrogate
10.0 out of 10, Exceptional, (11 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 ￥15,873
￥30,748 total
includes taxes & fees
Apr 12 - Apr 13
Harrogate Hideaway - 5 Min to LMU & Nat`l Park
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, (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 ￥12,857
￥26,932 total
includes taxes & fees
Apr 5 - Apr 6
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
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 ￥19,048
￥40,946 total
includes taxes & fees
Apr 5 - Apr 6
Beautiful Loft in the Woods
Property grounds

Robertson Ridge Hideaway Cottage

Robertson Ridge Hideaway Cottage
Hinkle
The price is ￥17,857
￥23,187 total
includes taxes & fees
Apr 2 - Apr 3
Robertson Ridge Hideaway Cottage
Interior

The Highlands Cabin Retreat at Norris Lake

The Highlands Cabin Retreat at Norris Lake
New Tazewell
10.0 out of 10, Exceptional, (3 reviews)
"The cabin was clean, cozy, and overall amazing! "
United States
Fannie
The price is ￥20,714
￥35,495 total
includes taxes & fees
Apr 2 - Apr 3
The Highlands Cabin Retreat at 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, (3 reviews)
"We stayed here for a wedding weekend in Pineville, KY, and it was absolutely perfect from start to finish. The home was spotless, cozy, and had everything we could possibly need. The beds were so comfortable, and we instantly felt at home the moment we walked in.What truly set this stay apart was the host’s kindness and above-and-beyond hospitality. We got lost in the middle of the night trying to find the property, and the host stayed on the phone with us, patiently guiding us right to the...
United States
Samantha P.
The price is ￥19,714
￥39,406 total
includes taxes & fees
Apr 2 - Apr 3
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
1 bedroom, free WiFi, bed sheets

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 ￥7,143
￥20,221 total
includes taxes & fees
Apr 8 - Apr 9
Quaint Studio APT Near ATV Trails & Norris Lake
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 ￥15,556
￥48,723 total
includes taxes & fees
Apr 2 - Apr 3
Peaceful & Private! Pet-friendly Williamsburg Home
Fridge, microwave, oven, stovetop

Harrogate Home Mountain View’s Dog Friendly

Harrogate Home Mountain View’s Dog Friendly
Harrogate
10.0 out of 10, Exceptional, (24 reviews)
"Great location with friendly neighbors!"
United States
Evan C.
The price is ￥25,000
￥47,348 total
includes taxes & fees
Apr 5 - Apr 6
Harrogate Home Mountain View’s Dog Friendly
Exterior

Blissful Bungalow across from LMU campus

Blissful Bungalow across from LMU campus
Harrogate
9.6 out of 10, Exceptional, (34 reviews)
"Cozy feel and relaxing. "
United States
Cynthia
The price is ￥17,460
￥35,068 total
includes taxes & fees
Apr 20 - Apr 21
Blissful Bungalow across from LMU campus
Outdoor dining

The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!

The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!
Pineville
9.4 out of 10, Exceptional, (3 reviews)
"The home was just perfect for what we needed. Looking forward to seeing how it comes out when all construction is finished! Host was very responsive. Will stay again"
United States
Kami L.
The price is ￥30,000
￥57,460 total
includes taxes & fees
Apr 2 - Apr 3
The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!
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

Quality Inn Harlan

Quality Inn Harlan

8/10 Good
"All good, no problems"
chris 1-night trip
Posted 1 day ago
Quality Inn Harlan

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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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?

Spacious Lake house with Double Boat Dock & Gently Sloping Lot: 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 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

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.