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Find Hotels with Free Parking in Middlesboro, KY

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Check availability on Middlesboro Hotels with Free Parking

Our top choices for Middlesboro hotels with parking

Standard Room | Desk, blackout drapes, iron/ironing board, rollaway beds
Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG
2.5 star property
Middlesboro
9.6 out of 10, Exceptional, (691)
"Clean hotel, good breakfast options."
United States
Harold
The price is NT$3,681
NT$4,058 total
includes taxes & fees
Dec 21 - Dec 22
Holiday Inn Express Middlesboro by IHG
In-room safe, desk, laptop workspace, blackout drapes
Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro
2.5 star property
Middlesboro
9.2 out of 10, Wonderful, (813)
"The breakfast was great and customer service was great! Very clean and beautiful views "
United States
Solange
The price is NT$2,917
NT$3,215 total
includes taxes & fees
Jan 4 - 2026/1/5
Sleep Inn & Suites Middlesboro
Double Room, Smoking | Desk, blackout drapes, free WiFi, bed sheets
Boone Trail Inn

Boone Trail Inn

Boone Trail Inn
2.0 star property
Middlesboro
7.2 out of 10, Good, (110)
"Place was clean. AC worked good. "
United States
David
The price is NT$2,106
NT$2,837 total
includes taxes & fees
Dec 15 - Dec 16
Boone Trail Inn
Standard Room, 2 Double Beds, Non Smoking | Laptop workspace, blackout drapes, iron/ironing board, free WiFi
Econo Lodge Middlesboro

Econo Lodge Middlesboro

Econo Lodge Middlesboro
2.0 star property
Middlesboro
7.4 out of 10, Good, (445)
"Clean place with friendly staff. "
United States
James
The price is NT$2,489
NT$2,744 total
includes taxes & fees
Dec 21 - Dec 22
Econo Lodge Middlesboro
Standard Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free WiFi, bed sheets
Suburban Studios Middlesboro

Suburban Studios Middlesboro

Suburban Studios Middlesboro
2.0 star property
Middlesboro
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
The price is NT$2,476
NT$2,730 total
includes taxes & fees
Dec 29 - Dec 30
Suburban Studios Middlesboro
Exterior
Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG
2.5 star property
Williamsburg
9.0 out of 10, Wonderful, (1000)
"Staff and room were great. We did not stay for breakfast because we wanted to get on the road home ASAP. "
United States
ROBERT
The price is NT$3,587
NT$4,057 total
includes taxes & fees
Jan 13 - 2026/1/14
Holiday Inn Express Williamsburg by IHG
Suite, 2 Queen Beds, Non Smoking | Bathroom | Combined shower/tub, deep soaking tub, hydromassage showerhead
Days Inn by Wyndham Jellico - Tennessee State Line

Days Inn by Wyndham Jellico - Tennessee State Line

Days Inn by Wyndham Jellico - Tennessee State Line
2.0 star property
Jellico
7.2 out of 10, Good, (1001)
"Very clean and quiet I loved and enjoyed my 3 nights and 4 day stay!!! "
United States
Antoninette
The price is NT$2,340
NT$2,673 total
includes taxes & fees
Jan 1 - 2026/1/2
Days Inn by Wyndham Jellico - Tennessee State Line
Business center
Quality Inn

Quality Inn

Quality Inn
2.5 star property
Barbourville
8.2 out of 10, Very Good, (267)
"Room was clean and clerk was nice especially since it was early morning "
United States
Billy
The price is NT$3,155
NT$3,579 total
includes taxes & fees
Jan 12 - 2026/1/13
Quality Inn
Sundeck
Cumberland Gap Inn

Cumberland Gap Inn

Cumberland Gap Inn
2.5 star property
Cumberland Gap
8.0 out of 10, Very Good, (584)
"The views around the area are beautiful and the town is peaceful and quiet "
United States
Robert
The price is NT$3,057
NT$3,462 total
includes taxes & fees
Dec 15 - Dec 16
Cumberland Gap Inn
Exterior
Quality Inn Harlan

Quality Inn Harlan

Quality Inn Harlan
2.5 star property
Harlan
8.6 out of 10, Excellent, (338)
"Room was nice and clean, staff very courteous, breakfast very good."
United States
Gary
The price is NT$2,779
NT$3,152 total
includes taxes & fees
Jan 4 - 2026/1/5
Quality Inn Harlan
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

Quality Inn

10/10 Excellent
"The room was very clean, staff was extremely friendly, polite, and helpful."
Katrina 2-night trip
Posted 6 days ago
Quality Inn

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