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Find Historic Hotels in Middlesboro, KY

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Check availability on Middlesboro Historic Hotels

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Recommended hotels in Middlesboro

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 ￥18,377
￥20,258 total
includes taxes & fees
Dec 21 - Dec 22
Holiday Inn Express Middlesboro by IHG
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 ￥10,391
￥14,026 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Boone Trail Inn
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 ￥14,538
￥16,027 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Sleep Inn & Suites Middlesboro
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 ￥12,428
￥13,702 total
includes taxes & fees
Dec 14 - Dec 15
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, (66)
"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 ￥12,343
￥13,607 total
includes taxes & fees
Dec 29 - Dec 30
Suburban Studios Middlesboro
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,

4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
Middlesboro
10.0 out of 10, Exceptional, (22)
"Great property! Very clean and homey!"
United States
Lillian I.
The price is ￥18,533
￥36,054 total
includes taxes & fees
Dec 14 - Dec 15
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
Exterior detail
Welcoming 3-bedroom house with AC in charming Middlesboro

Welcoming 3-bedroom house with AC in charming Middlesboro

Welcoming 3-bedroom house with AC in charming Middlesboro
Middlesboro
The price is ￥20,885
￥41,050 total
includes taxes & fees
Dec 15 - Dec 16
Welcoming 3-bedroom house with AC in charming Middlesboro
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.

Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Middlesboro
9.2 out of 10, Wonderful, (5)
"We enjoyed our stay. "
United States
Emily S.
The price is ￥27,255
￥57,688 total
includes taxes & fees
Dec 14 - Dec 15
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Microwave, oven, stovetop
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU

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)
"Clean"
United States
Phineas S.
The price is ￥57,468
￥90,994 total
includes taxes & fees
Dec 25 - Dec 26
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
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 ￥14,484
￥16,380 total
includes taxes & fees
Dec 23 - Dec 24
Holiday Inn Express Williamsburg by IHG
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.
View all properties

Top Middlesboro Hotel Reviews

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

10/10 Excellent
"Great hotel! Clean, updated, courteous and friendly staff and an outstanding breakfast! "
Carol 1-night trip
Posted 6 days ago
Sleep Inn & Suites Middlesboro

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Frequently asked questions

What should a history buff expect from a stay in Middlesboro?
A trip to the historical places in Middlesboro is probably first on your sightseeing itinerary. Why not appreciate the mountain landscape during your visit?
How many historical hotels will I find in Middlesboro?
In Middlesboro, there are 10 hotel accommodations bookable on Expedia but not many designated as historic hotels.
What are the top historical sites and other places to visit in Middlesboro?
Landmarks like Cumberland Gap National Historical Park and Bell County Historical Society Museum in Middlesboro might be worth a visit. A couple of additional sights to add to your agenda are Middlesboro Mall and Middlesboro Country Club.
What is a historic hotel like in Middlesboro?
By choosing a historic hotel, you can enjoy a vacation in a building that has an official historic designation. A stately home, palace or even a lodge, old police station, or skyscraper can be transformed into a historic hotel as long as it has special significance. Traditional architecture and period features are typically preserved in the guestrooms or communal spaces of these historic hotels in Middlesboro, bringing the history to life.
What is the difference between a historic hotel and a heritage hotel?
"Heritage hotel" is more common in Asia and Europe, while "historic hotel" is more common in the U.S. overall though the terms are similar. The architecture and actual building of historic hotels are generally the most significant aspect. For a heritage hotel, mainly, it's cultural value along with how it inspired the community.
Do historic hotels in Middlesboro have modern facilities?
Hotel interiors feature the modern conveniences and safety features you've come to expect, but every effort is made to preserve the historic aspects and traditions. Smart TVs, WiFi, updated bathroom facilities, and the amenities found in most hotels will also be available in a historic hotel. Rest assured that when you select a historic hotel in Middlesboro, you won't find a place that's uncomfortable or rundown.