An aerial view of a town surrounded by mountains, with a mix of residential and commercial buildings, and a highway running through the center.

Middlesboro Hotel Guide - Family Friendly Hotels in Middlesboro, Kentucky

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Check availability on Middlesboro Family Friendly Hotels

This weekend
10 Jul - 12 Jul
Next weekend
17 Jul - 19 Jul

Our top choices for Middlesboro family-friendly hotels

Exterior

Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG
2.5 star property
Williamsburg
9.0 out of 10, Wonderful, (1,004 reviews)
  • cleanliness
    Experience family fun in Williamsburg with an indoor pool, plush beds, and a splash park steps away for endless adventure.
The price is €111
includes taxes & fees
3 Aug - 4 Aug
Holiday Inn Express Williamsburg by IHG
In-room safe, desk, laptop workspace, blackout curtains

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro
2.5 star property
Middlesboro
9.2 out of 10, Wonderful, (898 reviews)
  • cleanliness
    Discover kid-friendly adventures near Cumberland Gap National Historical Park with comfy amenities and free breakfast.
The price is €109
includes taxes & fees
2 Aug - 3 Aug
Sleep Inn & Suites Middlesboro
Exterior

Quality Inn Harlan

Quality Inn Harlan
2.5 star property
Harlan
8.6 out of 10, Excellent, (368 reviews)
The price is €100
includes taxes & fees
19 Jul - 20 Jul
Quality Inn Harlan
Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, pool loungers

Pine Mountain State Resort Park

Pine Mountain State Resort Park
3.0 star property
Pineville
9.0 out of 10, Wonderful, (734 reviews)
The price is €147
includes taxes & fees
10 Jul - 11 Jul
Pine Mountain State Resort Park
House (2 Bedrooms) | Front of property

Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home
3.0 star property
Williamsburg
The price is €270
includes taxes & fees
11 Jul - 12 Jul
Peaceful & Private! Pet-friendly Williamsburg Home
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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Choose what matters most at family-friendly hotels in Middlesboro

Breakfast included
Pool

Top Middlesboro Hotel Reviews

Days Inn by Wyndham Jellico - Tennessee State Line

Days Inn by Wyndham Jellico - Tennessee State Line

8/10 Good
"the room was clean, pool was not open"
Cynthia 1-night trip
Posted 3 days ago
Days Inn by Wyndham Jellico - Tennessee State Line

Frequently asked questions

What's Middlesboro like for family-friendly holidays?
The destination of Middlesboro is a great choice if you've been thinking about a holiday with your children. The wildlife, glaciers and mountain views are just a few things that make this an attractive spot for a family holiday.
What's the best family accommodation 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 holiday in Middlesboro?
The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 5°C. Average annual precipitation for Middlesboro is 1581 mm.
What's there to see and do with your family in Middlesboro?
Middlesboro Mall and Bell County Public Library Pineville Branch are interesting attractions that you and your family may enjoy exploring while you are staying in Middlesboro. Make sure that you have lots of time for activities such as Kentucky Ridge State Forest and The Pinnacle.