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

Find Family Hotels in Middlesboro, KY

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Check availability on Middlesboro Family Hotels

Tonight
Aug 10 - Aug 11
Tomorrow
Aug 11 - Aug 12
This weekend
Aug 14 - Aug 16
Next weekend
Aug 21 - Aug 23

Our top choices for Middlesboro family-friendly hotels

In-room safe, desk, laptop workspace, blackout drapes
Lobby
Lobby
Free buffet breakfast

1. Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro
Middlesboro
  • Discover kid-friendly adventures near Cumberland Gap National Historical Park with comfy amenities and free breakfast.
NT$3,075
NT$3,459 total
includes taxes & fees
Sep 6 - Sep 7
Sleep Inn & Suites Middlesboro
Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers
BBQ/picnic area
Lobby lounge
Interior entrance

2. Pine Mountain State Resort Park

Pine Mountain State Resort Park
Pineville
NT$4,941
NT$5,447 total
includes taxes & fees
Aug 14 - Aug 15
Pine Mountain State Resort Park
Exterior
Free daily on-the-go breakfast
Fitness facility
Exterior

3. Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG
Williamsburg
  • Experience family fun in Williamsburg with an indoor pool, plush beds, and a splash park steps away for endless adventure.
NT$3,327
NT$3,703 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn Express Williamsburg by IHG
Exterior
Reception
Lobby lounge
In-room safe, desk, laptop workspace, blackout drapes

4. Quality Inn Harlan

Quality Inn Harlan
Harlan
NT$2,817
NT$3,195 total
includes taxes & fees
Sep 6 - Sep 7
Quality Inn Harlan
House (1 Bedroom) | Interior
House (1 Bedroom) | Interior
House (1 Bedroom) | Interior
House (1 Bedroom) | Front of property

5. Peaceful Mountain Cabin w/ Views in Williamsburg

Peaceful Mountain Cabin w/ Views in Williamsburg
Williamsburg
NT$4,070
NT$11,021 total
includes taxes & fees
Aug 11 - Aug 12
Peaceful Mountain Cabin w/ Views in Williamsburg
House (2 Bedrooms) | Front of property
House (2 Bedrooms) | Interior
House (2 Bedrooms) | Interior
House (2 Bedrooms) | Interior

6. Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home
Williamsburg
NT$4,070
NT$9,933 total
includes taxes & fees
Aug 22 - Aug 23
Peaceful & Private! Pet-friendly Williamsburg Home
View all properties

Choose what matters most at family-friendly hotels in Middlesboro

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Middlesboro Hotel Reviews

Days Inn by Wyndham Jellico - Tennessee State Line

Days Inn by Wyndham Jellico - Tennessee State Line

8/10 Good
"No one was in office but a note was on the door - be back soon. Waited only a few minutes. Did not turn on the TV but the internet was fine. McDonalds at bottom of the hill and can be entered from motel drive, avoiding going back to the street. Did not do breakfast, can't rate it. Park in front of your door, which I like. It was comfortable."
John F 1-night trip
Posted 3 days ago
Days Inn by Wyndham Jellico - Tennessee State Line
Quality Inn Harlan

Quality Inn Harlan

10/10 Excellent
"Beds were comfortable. Breakfast was hot. Pool was closed for maintenance"
Whitney 1-night trip
Posted 2 weeks ago
Quality Inn Harlan

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 C.W. Gose Municipal Park.

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