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Find Family Hotels in Middlesboro, KY

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Check availability on Middlesboro Family Hotels

Our top choices for Middlesboro family-friendly hotels

In-room safe, desk, laptop workspace, blackout drapes
Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro
2.5 star property
Middlesboro
9.2 out of 10, Wonderful, (813)
"The breakfast was great and customer service was great! Very clean and beautiful views "
United States
Solange
The price is ₩138,166
₩152,315 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Sleep Inn & Suites Middlesboro
Exterior
Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG
2.5 star property
Williamsburg
9.0 out of 10, Wonderful, (1001)
"Staff and room were great. We did not stay for breakfast because we wanted to get on the road home ASAP. "
United States
ROBERT
The price is ₩169,937
₩192,176 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Holiday Inn Express Williamsburg by IHG
Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers
Pine Mountain State Resort Park

Pine Mountain State Resort Park

Pine Mountain State Resort Park
3.0 star property
Pineville
9.0 out of 10, Wonderful, (669)
"The check in and out was very easy. Staff was pleasant and helpful. The cottage was very clean and well kept. The outside lighting could have been better as we arrived in the dark and it was hard to see. Overall great stay. "
United States
DeAnna
The price is ₩165,444
₩182,393 total
includes taxes & fees
Dec 26 - Dec 27
Pine Mountain State Resort Park
Exterior
Quality Inn Harlan

Quality Inn Harlan

Quality Inn Harlan
2.5 star property
Harlan
8.6 out of 10, Excellent, (338)
"Room was nice and clean, staff very courteous, breakfast very good."
United States
Gary
The price is ₩131,664
₩149,334 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Quality Inn Harlan
Sundeck
Cumberland Gap Inn

Cumberland Gap Inn

Cumberland Gap Inn
2.5 star property
Cumberland Gap
8.0 out of 10, Very Good, (584)
"Quaint Inn Friendly staff"
United States
Richard
The price is ₩144,816
₩164,011 total
includes taxes & fees
Dec 16 - Dec 17
Cumberland Gap Inn
Room, 2 Double Beds, Accessible, Non Smoking | Soundproofing, iron/ironing board, free cribs/infant beds, free WiFi
Super 8 by Wyndham Williamsburg

Super 8 by Wyndham Williamsburg

Super 8 by Wyndham Williamsburg
2.5 star property
Williamsburg
5.8 out of 10, (772)
"Price was right room was clean. Many choices to eat. Staff was pleasant. "
United States
Susan
The price is ₩85,412
₩95,063 total
includes taxes & fees
Dec 17 - Dec 18
Super 8 by Wyndham Williamsburg
House (2 Bedrooms) | Front of property
Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home
3.0 star property
Williamsburg
The price is ₩144,816
₩453,584 total
includes taxes & fees
Dec 16 - Dec 17
Peaceful & Private! Pet-friendly Williamsburg Home
Exterior
Rodeway Inn Harlan

Rodeway Inn Harlan

Rodeway Inn Harlan
2.0 star property
Harlan
5.6 out of 10, (231)
"Room was great , check in & staff was absolutely wonderful! "
United States
Hailey
The price is ₩75,614
₩85,760 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Rodeway Inn Harlan
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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Top Middlesboro Hotel Reviews

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

10/10 Excellent
"Great hotel! Clean, updated, courteous and friendly staff and an outstanding breakfast! "
Carol 1-night trip
Posted 10 days ago
Sleep Inn & Suites Middlesboro

Frequently asked questions

What's Middlesboro like for family-friendly vacations?
The destination of Middlesboro is a great choice if you've been thinking about a vacation with your kids. The wildlife, glaciers, and mountain views are just a few things that make this an attractive spot for a family vacation.
What's the best accommodation for families in Middlesboro?
Sleep Inn & Suites Middlesboro is a hotel with free parking and free buffet breakfast, and it's a top choice on Expedia for families.
When's the best time to book a family-friendly vacation in Middlesboro?
The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 40°F. Average annual precipitation for Middlesboro is 62 inches.
What's there to see and do with your family in Middlesboro?
Middlesboro Mall and Bell County Public Library Pineville Branch are interesting attractions you and your family might enjoy exploring while you are staying in Middlesboro. Make sure you have lots of time for activities like Kentucky Ridge State Forest and The Pinnacle.