Middlesboro Holidays
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Top hotels in Middlesboro
Sleep Inn & Suites Middlesboro
1260 N, 12th Street Middlesboro KY
Fully refundable
The price is S$149 per night from 31 May to 1 Jun
S$149
31 May - 1 Jun
includes taxes & fees
9.2/10 Wonderful! (870 reviews)
Lots of options, hot fresh coffee
Reviewed on 11 May, 2026
Econo Lodge Middlesboro
1623 Cumberland Avenue Middlesboro KY
Fully refundableReserve now, pay when you stay
The price is S$110 per night from 29 May to 30 May
S$110
29 May - 30 May
includes taxes & fees
7.4/10 Good! (467 reviews)
Very nice people working there. Will stay again. Room we rented was nice and clean
Reviewed on 13 May, 2026
Holiday Inn Express Middlesboro by IHG
1252 N 12th St Middlesboro KY
The price is S$192 per night from 17 May to 18 May
S$192
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
