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Search and Rent Middlesboro Condos

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Recommended hotels in Middlesboro

Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG
2.5 star property
9.6 out of 10, Exceptional, (694)
"Only stayed one night but the hotel was quiet, considering the amount of people that seemed to be there, very clean and the breakfast was great!"
United States
Kevin
$125 nightly
The price is $138
Jan 11 - Jan 12, 2026
Total with taxes and fees
Holiday Inn Express Middlesboro by IHG

Motel in Middlesboro

Boone Trail Inn
2.0 star property
7.2 out of 10, Good, (111)
"So the room seemed clean and the owners were vry kind the price was low all in all it was ok for a cheap motel but yall theres roaches i woke up with 1 crawling on the headboard. "
United States
Amy
$76 nightly
The price is $84
Dec 30 - Dec 31
Total with taxes and fees
Boone Trail Inn

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro
2.5 star property
9.2 out of 10, Wonderful, (815)
"Room was clean and comfortable. Staff was courteous. "
United States
Tommy
$94 nightly
The price is $103
Jan 18 - Jan 19, 2026
Total with taxes and fees
Sleep Inn & Suites Middlesboro

Suburban Studios Middlesboro

Suburban Studios Middlesboro
2.0 star property
8.0 out of 10, Very Good, (67)
"The newly renovated very clean room was comfortable and clean. All staff were very friendly and we had no issues with our stay. Would stay again when in this area! "
United States
Becky
$78 nightly
The price is $86
Jan 4 - Jan 5, 2026
Total with taxes and fees
Suburban Studios Middlesboro

Motel in Middlesboro

Econo Lodge Middlesboro
2.0 star property
7.4 out of 10, Good, (446)
"Clean place with friendly staff. "
United States
James
$89 nightly
The price is $98
Dec 31 - Jan 1, 2026
Total with taxes and fees
Econo Lodge Middlesboro
10.0 out of 10, Exceptional, (23)
"Very nice and extra clean great time"
United States
Johnny C.
$210 nightly
The price is $232
Dec 30 - Dec 31
Total with taxes and fees
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
10.0 out of 10, Exceptional, (1)
"Clean"
United States
Phineas S.
$272 nightly
The price is $299
Jan 21 - Jan 22, 2026
Total with taxes and fees
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
9.2 out of 10, Wonderful, (5)
"We enjoyed our stay. "
United States
Emily S.
$336 nightly
The price is $370
Dec 30 - Dec 31
Total with taxes and fees
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
$250 nightly
The price is $276
Jan 25 - Jan 26, 2026
Total with taxes and fees
Welcoming 3-bedroom house with AC in charming Middlesboro

Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG
2.5 star property
9.0 out of 10, Wonderful, (1003)
"Staff was nice and breakfast was good"
United States
nicole
$117 nightly
The price is $130
Jan 13 - Jan 14, 2026
Total with taxes and fees
Holiday Inn Express Williamsburg by IHG

Quality Inn Harlan

Quality Inn Harlan
2.5 star property
8.6 out of 10, Excellent, (340)
"Room was nice and clean, staff very courteous, breakfast very good."
United States
Gary
$89 nightly
The price is $101
Jan 4 - Jan 5, 2026
Total with taxes and fees
Quality Inn Harlan

Days Inn by Wyndham Jellico - Tennessee State Line

Days Inn by Wyndham Jellico - Tennessee State Line
2.0 star property
7.2 out of 10, Good, (1002)
"Nice location, nice room, friendly staff and recent remodeling rooms "
United States
Ashley
$74 nightly
The price is $85
Jan 4 - Jan 5, 2026
Total with taxes and fees
Days Inn by Wyndham Jellico - Tennessee State Line

Pine Mountain State Resort Park

Pine Mountain State Resort Park
3.0 star property
9.0 out of 10, Wonderful, (673)
"Great place to stay!"
United States
William
$125 nightly
The price is $138
Dec 31 - Jan 1, 2026
Total with taxes and fees
Pine Mountain State Resort Park

Imperial Inn by OYO Tazewell

Imperial Inn by OYO Tazewell
2.5 star property
9.0 out of 10, Wonderful, (48)
"Great hotel"
United States
Tahir
$78 nightly
The price is $89
Jan 1 - Jan 2, 2026
Total with taxes and fees
Imperial Inn by OYO Tazewell

Bed & Breakfast in Cumberland Gap

The Olde Mill Inn Bed & Breakfast
2.5 star property
9.0 out of 10, Wonderful, (426)
"Staff was very communicative, room was clean with all necessary amenities. Good location. Comfy beds. "
United States
Jennifer
$149 nightly
The price is $169
Jan 15 - Jan 16, 2026
Total with taxes and fees
The Olde Mill Inn Bed & Breakfast
3.0 star property
9.4 out of 10, Exceptional, (142)
"Gym was closed, restaurant was closed... pool was nice. Course is beautiful."
United States
Daniel
$130 nightly
The price is $146
Jan 1 - Jan 2, 2026
Total with taxes and fees
Woodlake Lodge Golf and Country Club

Quality Inn

Quality Inn
2.5 star property
8.2 out of 10, Very Good, (267)
"Room was clean and clerk was nice especially since it was early morning "
United States
Billy
$101 nightly
The price is $114
Jan 18 - Jan 19, 2026
Total with taxes and fees
Quality Inn

Motel in Cumberland Gap

Cumberland Gap Inn
2.5 star property
8.0 out of 10, Very Good, (585)
"Clean love the people we always stay there when we travel south"
United States
Christopher
$98 nightly
The price is $111
Dec 30 - Dec 31
Total with taxes and fees
Cumberland Gap Inn
10.0 out of 10, Exceptional, (4)
"Everything was clean and felt like home.host was really nice and I will definitely be staying again."
United States
Nicholas H.
$146 nightly
The price is $161
Jan 5 - Jan 6, 2026
Total with taxes and fees
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!

Apartment in Harlan

Beautiful Loft in the Woods
10.0 out of 10, Exceptional, (3)
"Beautiful setting. Incredible space well laid out. Owner was very engaging. "
United States
Fred
$212 nightly
The price is $234
Dec 30 - Dec 31
Total with taxes and fees
Beautiful Loft in the Woods
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

Middlesboro Condo Rentals information

Number of reviews
6,396
Accommodation
1 Condo Rentals
Lowest Price
$84
Highest Price
$370

Frequently asked questions

Why book your condo in Middlesboro with Expedia?
Expedia will help you find your ideal condo in Middlesboro. After a luxury escape? Make use of our filters to search for properties that have a 5-star rating. If you're on a budget, choose how much you want to spend and then check out our amazing deals. We'll help you find the right place whatever your trip looks like.
How can I find cheap condos in Middlesboro?
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What is there to do in Middlesboro near my condo?
The most practical travel accessory is a well-planned schedule. Middlesboro Mall is a terrific place to kick-start your adventures in Middlesboro.

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