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
Sep 13 - Sep 14
Tomorrow
Sep 14 - Sep 15
Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27

Our top choices for Middlesboro family-friendly hotels

Room
Breakfast area
Lobby
Lobby

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.
₩143,685
₩161,242 total
includes taxes & fees
Sep 27 - Sep 28
Sleep Inn & Suites Middlesboro
Outdoor pool
Interior entrance
BBQ/picnic area
Lobby lounge

2. Pine Mountain State Resort Park

Pine Mountain State Resort Park
Pineville
₩139,459
₩153,747 total
includes taxes & fees
Sep 20 - Sep 21
Pine Mountain State Resort Park
Front of property - evening/night
Fitness facility
Room
Standard Room, 1 King Bed, Accessible (Mobility, Roll-In Shower) | Bathroom

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.
₩158,309
₩176,198 total
includes taxes & fees
Sep 17 - Sep 18
Holiday Inn Express Williamsburg by IHG
Exterior
Lobby lounge
Reception
Room

4. Quality Inn Harlan

Quality Inn Harlan
Harlan
₩119,617
₩135,668 total
includes taxes & fees
Oct 11 - Oct 12
Quality Inn Harlan
House (2 Bedrooms) | Front of property
House (2 Bedrooms) | Interior
House (2 Bedrooms) | Interior
House (2 Bedrooms) | Interior

5. Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home
Williamsburg
₩169,042
₩412,502 total
includes taxes & fees
Sep 14 - Sep 15
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

10/10 Excellent
"Need pool open"
Bobby 2-night trip
Posted 2 days ago
Days Inn by Wyndham Jellico - Tennessee State Line
Quality Inn Harlan

Quality Inn Harlan

8/10 Good
"Clean room, property has been updated, fast several options great place for a quick overnight trip"
Rhett 1-night trip
Posted 7 days 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 Norris Lake.

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