Middlesboro Holidays
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Middlesboro Holiday
Our pick of the best Middlesboro Hotel Deals
Sleep Inn & Suites Middlesboro
1260 N, 12th Street Middlesboro KY
Fully refundable
The price is NZ$184 per night from 22 Feb to 23 Feb
NZ$184
22 Feb - 23 Feb
includes taxes & fees
9/10 Wonderful! (820 reviews)
Belinda at the desk is amazing She made our stay excellent , she made us feel like we were old friends . We will be staying here on each visit .
Reviewed on 24 Jan 2026
Boone Trail Inn
2105 US HIGHWAY 25 E Middlesboro KY
Fully refundableReserve now, pay when you stay
The price is NZ$138 per night from 14 Feb to 15 Feb
NZ$138
14 Feb - 15 Feb
includes taxes & fees
7.2/10 Good! (108 reviews)
The owners and staff were quite nice. The owner brought me a blanket without me having to ask since the temp was going to drop into the 40s. Inside,the owners have done an excellent update of the rooms.Excellent value for the money.
Reviewed on 21 Oct 2025
Holiday Inn Express Williamsburg by IHG
56 West Highway 92 Williamsburg KY
Fully refundable
The price is NZ$225 per night from 25 Feb to 26 Feb
NZ$225
25 Feb - 26 Feb
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
Pleasant front desk staff. Room was clean spacious room with comfortable bedding. Continental breakfast was decent and always comes in handy! Located close to Walmart and fast food restaurants for quick shopping and dining.
Reviewed on 7 Feb 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.
