Middlesboro Hotel Guide - Family Friendly Hotels in Middlesboro, Kentucky
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22 Aug - 23 AugTomorrow
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28 Aug - 30 AugIn two weeks
4 Sept - 6 SeptOur 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.
€102
includes taxes & fees
21 Sept - 22 Sept
€144
includes taxes & fees
28 Aug - 29 Aug
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.
€105
includes taxes & fees
1 Sept - 2 Sept
€232
includes taxes & fees
24 Aug - 25 Aug
€85
includes taxes & fees
13 Sept - 14 Sept
6. Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg
Peaceful ‘Mountain Cabin’ w/ Views in WilliamsburgWilliamsburg
€304
includes taxes & fees
23 Aug - 24 Aug
7. Peaceful & Private! Pet-friendly Williamsburg Home
Peaceful & Private! Pet-friendly Williamsburg HomeWilliamsburg
€263
includes taxes & fees
23 Aug - 24 Aug
8. Peaceful & Private! Pet-Friendly Williamsburg Home
Peaceful & Private! Pet-Friendly Williamsburg HomeWilliamsburg
€266
includes taxes & fees
23 Aug - 24 Aug
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Top Middlesboro Hotel Reviews
Lake Front 2-Bedroom Home W/ Privacy! Beautiful Views & Numerous Amenities...
10/10 Excellent
"We just spent an incredible week at this beautiful summer cottage in Tennessee, and it exceeded every expectation. The cottage was spotless, beautifully maintained, and had everything we needed to feel right at home from the moment we arrived.The views were absolutely breathtaking. Whether enjoying coffee on the porch in the morning or relaxing in the evening, the scenery was peaceful and unforgettable. We were also lucky to have perfect weather all week, which made spending time outdoors even more enjoyable.The location was ideal—quiet, relaxing, and the perfect place to unwind while still being close enough to explore the surrounding area. Every detail of the cottage showed how much care the owners put into making guests feel welcome.If you’re looking for a clean, comfortable, and scenic getaway in Tennessee, this is the place. We made wonderful memories here and would absolutely stay again. Highly recommend!"
Quality Inn Harlan
10/10 Excellent
"Beds were comfortable. Breakfast was hot. Pool was closed for maintenance"