Photo by Alexis Wyrick

Find Historic Hotels in Middlesboro, KY

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check availability on Middlesboro Historic Hotels

Tonight
Oct 26 - Oct 27
Tomorrow
Oct 27 - Oct 28
Next weekend
Oct 31 - Nov 2
In two weeks
Nov 7 - Nov 9

Top Middlesboro Historic Hotels

We don't have any properties that match your exact search
See all properties in Middlesboro

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
2.5 star property
9.6 out of 10, Exceptional, (683)
"Great breakfast. Room was spacious, clean and the dove products in the bathroom were nice. Great stay. "
United States
Rachel
The price is ￥18,343
￥20,222 total
includes taxes & fees
Nov 16 - Nov 17
Holiday Inn Express Middlesboro by IHG
Double Room, Smoking | Desk, blackout drapes, free WiFi, bed sheets
Boone Trail Inn
Boone Trail Inn
2.0 star property
7.2 out of 10, Good, (107)
"Place was clean. AC worked good. "
United States
David
The price is ￥9,493
￥12,992 total
includes taxes & fees
Nov 14 - Nov 15
Boone Trail Inn
Exterior
Sleep Inn & Suites Middlesboro
Sleep Inn & Suites Middlesboro
2.5 star property
9.2 out of 10, Wonderful, (797)
"Clean, super nice staff, bed comfortable "
United States
Kay
The price is ￥14,292
￥15,755 total
includes taxes & fees
Nov 9 - Nov 10
Sleep Inn & Suites Middlesboro
Standard Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free WiFi, bed sheets
Suburban Studios Middlesboro
Suburban Studios Middlesboro
2.0 star property
8.0 out of 10, Very Good, (63)
"Didn't stay as we found a better location in Cumberland Gap. "
United States
Alan
The price is ￥11,556
￥12,740 total
includes taxes & fees
Nov 8 - Nov 9
Suburban Studios Middlesboro
Standard Room, 2 Double Beds, Non Smoking | Laptop workspace, blackout drapes, iron/ironing board, free WiFi
Econo Lodge Middlesboro
Econo Lodge Middlesboro
2.0 star property
7.2 out of 10, Good, (440)
"Clean place with friendly staff. "
United States
James
The price is ￥12,198
￥13,448 total
includes taxes & fees
Nov 23 - Nov 24
Econo Lodge 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,
10.0 out of 10, Exceptional, (19)
"Our group had a wonderful time staying at Uncle Ernie's! Everything was neat, tidy, and felt like home. We definitely will be back next time we are in the area!"
United States
Savannah P.
The price is ￥18,190
￥35,555 total
includes taxes & fees
Nov 3 - Nov 4
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
The price is ￥18,221
￥37,445 total
includes taxes & fees
Nov 2 - Nov 3
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.
9.2 out of 10, Wonderful, (5)
"We enjoyed our stay. "
United States
Emily S.
The price is ￥25,680
￥55,440 total
includes taxes & fees
Nov 4 - Nov 5
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
The price is ￥56,405
￥90,153 total
includes taxes & fees
Oct 27 - Oct 28
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
Outdoor wedding area
Pine Mountain State Resort Park
Pine Mountain State Resort Park
3.0 star property
9.0 out of 10, Wonderful, (639)
"Great views, and wonderful trails, and pet-friendly."
United States
Frederick
The price is ￥17,848
￥19,676 total
includes taxes & fees
Nov 8 - Nov 9
Pine Mountain State Resort Park
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

Sleep Inn & Suites

10/10 Excellent
"Was clean and well maintained property. "
Mark 1-night trip
Posted 6 days ago
Sleep Inn & Suites

Explore a world of travel with Expedia

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.