Find Family Hotels in Middlesboro, KY
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25 Sep - 27 SepOur top choices for Middlesboro family-friendly hotels
1. Sleep Inn & Suites Middlesboro
Sleep Inn & Suites MiddlesboroMiddlesboro
- Discover kid-friendly adventures near Cumberland Gap National Historical Park with comfy amenities and free breakfast.
AED 393
AED 441 total
includes taxes & fees
27 Sep - 28 Sep
AED 382
AED 421 total
includes taxes & fees
20 Sep - 21 Sep
3. Holiday Inn Express Williamsburg by IHG
Holiday Inn Express Williamsburg by IHGWilliamsburg
- Experience family fun in Williamsburg with an indoor pool, plush beds, and a splash park steps away for endless adventure.
AED 433
AED 482 total
includes taxes & fees
22 Sep - 23 Sep
AED 332
AED 376 total
includes taxes & fees
11 Oct - 12 Oct
AED 496
AED 1,003 total
includes taxes & fees
20 Sep - 21 Sep
6. Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley MarinaSpeedwell
AED 298
AED 623 total
includes taxes & fees
22 Sep - 23 Sep
7. Peaceful & Private! Pet-friendly Williamsburg Home
Peaceful & Private! Pet-friendly Williamsburg HomeWilliamsburg
AED 463
AED 1,129 total
includes taxes & fees
18 Sep - 19 Sep
8. Peaceful & Private! Pet-Friendly Williamsburg Home
Peaceful & Private! Pet-Friendly Williamsburg HomeWilliamsburg
AED 323
AED 1,142 total
includes taxes & fees
21 Sep - 22 Sep
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Top Middlesboro Hotel Reviews
Holiday Inn Express Middlesboro by IHG
10/10 Excellent
"We had a wonderful stay at the Holiday Inn Express in Middlesboro, KY. The staff truly made our visit special—they were incredibly pleasant, helpful, and always made sure all of our needs were met. Every single day, we were greeted with warm smiles and friendly faces. They even went out of their way to give us excellent local recommendations for dinner. Their outstanding customer service made us feel right at home. We highly recommend this hotel to anyone visiting the area!"
Sleep Inn & Suites Middlesboro
10/10 Excellent
"Extremely convenient location for visiting Cumberland Gap National Park and surrounding area. This is a very pleasant town. The staff were very helpful and pleasant."