Photo by Alexis Wyrick

Search Family-Friendly Hotels in Middlesboro

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Middlesboro Family-Friendly Hotels

Top Middlesboro Family-Friendly Hotels

Exterior
Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

2.5 star property
Middlesboro
9.2 out of 10, Wonderful, (802)
"Clean, super nice staff, bed comfortable "
United States
Kay
The price is 2.463.725 ₫
2.716.011 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Sleep Inn & Suites Middlesboro
Outdoor wedding area
Pine Mountain State Resort Park

Pine Mountain State Resort Park

3.0 star property
Pineville
9.0 out of 10, Wonderful, (656)
"Staff were amazing! Very unique experience in the cottage and the fireplace was really special highly recommended!"
United States
Andrew
The price is 2.870.042 ₫
3.164.108 ₫ total
includes taxes & fees
23 Nov - 24 Nov
Pine Mountain State Resort Park
Exterior
Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG

2.5 star property
Williamsburg
9.0 out of 10, Wonderful, (1003)
"We really enjoyed our stay! "
United States
Andrea Strode
The price is 3.056.600 ₫
3.456.594 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Holiday Inn Express Williamsburg by IHG
Exterior
Quality Inn

Quality Inn

2.5 star property
Harlan
8.6 out of 10, Excellent, (330)
"The breakfast was great and the parking lot felt safe and had plenty of lighting. Overall a good stay."
United States
James
The price is 2.435.531 ₫
2.762.379 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Quality Inn
Honeymoon Suite, 1 King Bed | 1 bedroom, laptop workspace, free WiFi, bed sheets
Cumberland Gap Inn

Cumberland Gap Inn

2.5 star property
Cumberland Gap
8.0 out of 10, Very good, (583)
"The views around the area are beautiful and the town is peaceful and quiet "
United States
Robert
The price is 2.582.300 ₫
2.924.587 ₫ total
includes taxes & fees
18 Nov - 19 Nov
Cumberland Gap Inn
House (2 Bedrooms) | Interior
Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home

3.0 star property
Williamsburg
The price is 2.845.800 ₫
7.422.005 ₫ total
includes taxes & fees
18 Nov - 19 Nov
Peaceful & Private! Pet-friendly Williamsburg Home
Exterior
Super 8 by Wyndham Williamsburg

Super 8 by Wyndham Williamsburg

2.5 star property
Williamsburg
5.8 out of 10, (758)
"Love the Mint.."
United States
Tracy
The price is 1.657.415 ₫
1.844.702 ₫ total
includes taxes & fees
1 Dec - 2 Dec
Super 8 by Wyndham Williamsburg
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.
View all properties

Top Middlesboro Hotel Reviews

Explore a world of travel with Expedia

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.
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.