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Find Family Hotels in Middlesboro, KY

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Check availability on Middlesboro Family Hotels

Tonight
Dec 25 - Dec 26
Tomorrow
Dec 26 - Dec 27
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Middlesboro family-friendly hotels

Exterior
Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro
2.5 star property
Middlesboro
9.2 out of 10, Wonderful, (815)
"Room was clean and comfortable. Staff was courteous. "
United States
Tommy
The price is ￥14,580
￥16,074 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Sleep Inn & Suites Middlesboro
3 bedrooms, desk, iron/ironing board, travel crib
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Middlesboro
9.2 out of 10, Wonderful, (5)
"We enjoyed our stay. "
United States
Emily S.
The price is ￥27,290
￥57,934 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
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, (1000)
"Staff was nice and breakfast was good"
United States
nicole
The price is ￥17,933
￥20,280 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, (672)
"Great place to stay!"
United States
William
The price is ￥14,964
￥16,497 total
includes taxes & fees
Jan 3 - Jan 4, 2026
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, (340)
"Room was nice and clean, staff very courteous, breakfast very good."
United States
Gary
The price is ￥13,894
￥15,759 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Quality Inn Harlan
Honeymoon Suite, 1 King Bed | Laptop workspace, free WiFi, bed sheets
Cumberland Gap Inn

Cumberland Gap Inn

Cumberland Gap Inn
2.5 star property
Cumberland Gap
8.0 out of 10, Very Good, (585)
"Quaint Inn Friendly staff"
United States
Richard
The price is ￥15,282
￥17,308 total
includes taxes & fees
Dec 27 - Dec 28
Cumberland Gap Inn
Exterior
Rodeway Inn Harlan

Rodeway Inn Harlan

Rodeway Inn Harlan
2.0 star property
Harlan
5.6 out of 10, (232)
"Room was great , check in & staff was absolutely wonderful! "
United States
Hailey
The price is ￥7,727
￥8,765 total
includes taxes & fees
Dec 28 - Dec 29
Rodeway Inn Harlan
House (2 Bedrooms) | Interior
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 ￥15,282
￥47,866 total
includes taxes & fees
Dec 28 - Dec 29
Peaceful & Private! Pet-friendly Williamsburg Home
Exterior
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, (774)
"Price was right room was clean. Many choices to eat. Staff was pleasant. "
United States
Susan
The price is ￥9,278
￥10,327 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Super 8 by Wyndham Williamsburg
Children's area
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 Marina

Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
Speedwell
9.4 out of 10, Exceptional, (19)
"It was exceptional "
United States
Dennis W.
The price is ￥11,228
￥24,856 total
includes taxes & fees
Dec 28 - Dec 29
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
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
"Room was clean and comfortable. Staff was courteous. "
Tommy 3-night trip
Posted 2 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.