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 13 - Aug 14
Tomorrow
Aug 14 - Aug 15
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
Exterior
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$3,180
NT$3,574 total
includes taxes & fees
Sep 10 - Sep 11
Sleep Inn & Suites Middlesboro
Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers
Lobby lounge
BBQ/picnic area
Interior entrance

2. Pine Mountain State Resort Park

Pine Mountain State Resort Park
Pineville
NT$4,933
NT$5,438 total
includes taxes & fees
Aug 14 - Aug 15
Pine Mountain State Resort Park
Exterior
Fitness facility
1 bedroom, premium bedding, pillowtop beds, in-room safe
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$3,548
NT$3,949 total
includes taxes & fees
Aug 17 - Aug 18
Holiday Inn Express Williamsburg by IHG
Exterior
Free daily continental breakfast
Reception
Lobby lounge

4. Quality Inn Harlan

Quality Inn Harlan
Harlan
NT$2,821
NT$3,199 total
includes taxes & fees
Sep 6 - Sep 7
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
NT$4,064
NT$9,917 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

Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG

10/10 Excellent
"The gym is janky and almost scary. It’s very dark and just very isolated. Scary as a female to go to alone. Otherwise nice property. Gym is important to me so I would not stay here again. But I would not discourage someone who isn’t concerned about a gym to stay."
Shelley 1-night trip
Posted 5 hours ago
Holiday Inn Express Middlesboro by IHG
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 3 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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