Middlesboro Holidays from £1,061
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Your Middlesboro Holiday
From its rich history to its spectacular views and beyond, there's a lot to like about Middlesboro. Discover the wonders of this interesting city with a Middlesboro holiday package that's made for you. If taking in sights is on the agenda during your trip to Middlesboro, check out popular attractions like Cumberland Gap National Historical Park, Middlesboro Mall and Bell County Historical Society Museum. Your ideal Middlesboro holiday is just clicks away. Browse accommodation, flights and more on Expedia for an adventure that's tailored to suit your travel style.
Top Middlesboro Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Margaritaville Island Hotel
Downtown Pigeon Forge
Price was £1,940, price is now £1,584 per person
£1,584
per person
15 Jun - 22 Jun
found 3 hours ago
Return direct flight included
Manchester (MAN) to Knoxville (TYS)
9.4/10 Exceptional! (1,293 reviews)
No breakfast menu. Hanging towels next to toilet, garbage piled up even though we didn't have a Do Not Disturb. Only took garbage one day. Black bugs on sink and in bed, they say leave dirty towels on the floor left my dirty washcloths on the shower floor. Never picked up. Very disappointed the amount of money we spent the rooms are beautiful. But the cleaning staff nowhere to be seen. One morning we were leaving she asked us if we needed anything I asked for extra creamer she didn't even do that. We usually stay at BNBs this is our first time in a hotel after many years and so very saddened by it
Reviewed on 5 May 2026
Arbors at Island Landing Hotel & Suites
Downtown Pigeon Forge
Price was £1,288, price is now £1,140 per person
£1,140
per person
15 Jun - 22 Jun
found 3 hours ago
Return direct flight included
Manchester (MAN) to Knoxville (TYS)
9.6/10 Exceptional! (1,105 reviews)
The problem was the elevator was out o service for one of our days we are in our 70's it was very hard to walk up 5 flights of steps and back down
Reviewed on 8 May 2026
Holiday Inn & Suites Pigeon Forge Convention Center by IHG
Downtown Pigeon Forge
Price was £1,471, price is now £1,303 per person
£1,303
per person
15 Jun - 22 Jun
found 3 hours ago
Return direct flight included
Manchester (MAN) to Knoxville (TYS)
9/10 Wonderful! (1,007 reviews)
Fair price for what is served
Reviewed on 26 Apr 2026
Pinot Paradise
Price was £2,308, price is now £2,049 per person
£2,049
per person
15 Jun - 22 Jun
found 3 hours ago
Return direct flight included
Manchester (MAN) to Knoxville (TYS)
9/10 Wonderful! (2 reviews)
the house was so beautiful! so spacious, clean and communication with owner was great!
Reviewed on 23 Jan 2026
Middlesboro Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 10,700 |
Max Temp Winter | 7ºC |
Max Temp Summer | 29ºC |
Top Sights | Pine Mountain State Resort Park, Bell County Historical Society Museum and Middlesboro Mall |
Top hotels in Middlesboro
Sleep Inn & Suites Middlesboro
1260 N, 12th Street Middlesboro KY
Fully refundable
The price is £84 per night from 31 May to 1 Jun
£84
31 May - 1 Jun
includes taxes & fees
9.2/10 Wonderful! (865 reviews)
Great location, big room, great breakfast.
Reviewed on 7 May 2026
Econo Lodge Middlesboro
1623 Cumberland Avenue Middlesboro KY
Fully refundableReserve now, pay when you stay
The price is £64 per night from 25 May to 26 May
£64
25 May - 26 May
includes taxes & fees
7.4/10 Good! (463 reviews)
The rooms wwre nice and clean. Small breakfast but good
Reviewed on 5 May 2026
Holiday Inn Express Middlesboro by IHG
1252 N 12th St Middlesboro KY
Fully refundable
The price is £111 per night from 17 May to 18 May
£111
17 May - 18 May
includes taxes & fees
9.6/10 Exceptional! (719 reviews)
Convenient location to Cumberland Gap National Park. Was a quiet hotel. Our room looked out to a section of the hillside. Restaurants within walking distance and Walmart was across the street.
Reviewed on 5 May 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
