Find Historic Hotels in Cumberland Gap, TN

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Check availability on Cumberland Gap Historic Hotels

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Recommended hotels in Cumberland Gap

Suite, Accessible, Ensuite (Thomas Walker Annex) | 1 bedroom, WiFi
The Olde Mill Inn Bed & Breakfast

The Olde Mill Inn Bed & Breakfast

The Olde Mill Inn Bed & Breakfast
2.5 star property
Cumberland Gap
9.0 out of 10, Wonderful, (425)
"Nice place in historic Cumberland Gap, walkable to hiking trail and pave local trail. The room is spacious, very clean, and comfortable bed. Homemade breakfast was delicious."
United States
Ry
The price is NT$4,183
NT$4,737 total
includes taxes & fees
Jan 16 - 2026/1/17
The Olde Mill Inn Bed & Breakfast
Honeymoon Suite, 1 King Bed | Laptop workspace, free WiFi, bed sheets
Cumberland Gap Inn

Cumberland Gap Inn

Cumberland Gap Inn
2.5 star property
Cumberland Gap
8.0 out of 10, Very Good, (584)
"Quaint Inn Friendly staff"
United States
Richard
The price is NT$3,057
NT$3,462 total
includes taxes & fees
Jan 16 - 2026/1/17
Cumberland Gap Inn
Outdoor wedding area
Pine Mountain State Resort Park

Pine Mountain State Resort Park

Pine Mountain State Resort Park
3.0 star property
Pineville
9.0 out of 10, Wonderful, (669)
"The check in and out was very easy. Staff was pleasant and helpful. The cottage was very clean and well kept. The outside lighting could have been better as we arrived in the dark and it was hard to see. Overall great stay. "
United States
DeAnna
The price is NT$3,512
NT$3,872 total
includes taxes & fees
Dec 26 - Dec 27
Pine Mountain State Resort Park
Front of property
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, (1002)
"Very clean and quiet I loved and enjoyed my 3 nights and 4 day stay!!! "
United States
Antoninette
The price is NT$2,321
NT$2,652 total
includes taxes & fees
Jan 1 - 2026/1/2
Days Inn by Wyndham Jellico - Tennessee State Line
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, (692)
"Clean hotel, good breakfast options."
United States
Harold
The price is NT$3,701
NT$4,080 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, (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
The price is NT$2,106
NT$2,837 total
includes taxes & fees
Jan 16 - 2026/1/17
Boone Trail Inn
Aerial view
Woodlake Lodge Golf and Country Club

Woodlake Lodge Golf and Country Club

Woodlake Lodge Golf and Country Club
3.0 star property
Tazewell
9.4 out of 10, Exceptional, (142)
"Gym was closed, restaurant was closed... pool was nice. Course is beautiful."
United States
Daniel
The price is NT$4,055
NT$4,552 total
includes taxes & fees
Jan 16 - 2026/1/17
Woodlake Lodge Golf and Country Club
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 Cumberland Gap 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 11 days ago
Sleep Inn & Suites Middlesboro

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Frequently asked questions

What should a history enthusiast expect from a trip to Cumberland Gap?
You'll probably want to seek out the sights of historical relevance while you're staying in Cumberland Gap. Also explore the many sights to visit such as riverfront and mountain views
How many historical hotels are there in Cumberland Gap?
Cumberland Gap is home to 5 hotels and other accommodations bookable on Expedia though not many historic hotels to choose from.
What are the most important historical sites and other places in Cumberland Gap?
Cumberland Gap is notable for landmarks like Cumberland Gap National Historical Park. You'll also find The Pinnacle and Pine Mountain State Resort Park in the area.
What is a historic hotel like in Cumberland Gap?
By choosing a historic hotel, you can stay in a place that has an officially recognized historic designation. A stately home, palace or even a lodge, old police station, or skyscraper can be identified as a historic hotel as long as it has special significance. Traditional architecture and period features are typically preserved in the communal spaces and guestrooms of these historic hotels in Cumberland Gap, bringing the history to life.
What is the difference between a historic hotel and a heritage hotel?
You'll often hear the term "heritage hotel" in Asia and Europe, while "historic hotel" is a term often used in the U.S. though overall the terms are quite similar. The building and architecture of historic hotels tend to be what's most important. For a heritage hotel, it's mainly the cultural value as well as how it shaped the community.
Do historic hotels in Cumberland Gap have modern facilities?
Hotels include modern conveniences and safety features you expect to find, while every effort is made to preserve historic facades and treasured traditions. Smart TVs, WiFi, updated bathroom facilities, and the popular amenities found at a contemporary hotel should be available at a historic hotel. Rest assured that when you select a historic hotel in Cumberland Gap, you won't find yourself staying at a place that is rundown or uncomfortable.