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

  • 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 Hotels

Tonight
9 Sep - 10 Sep
Tomorrow
10 Sep - 11 Sep
This weekend
11 Sep - 13 Sep
Next weekend
18 Sep - 20 Sep

Our top choices for Middlesboro family-friendly hotels

In-room safe, desk, laptop workspace, blackout drapes
Lobby
Exterior
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.
AED 393
AED 441 total
includes taxes & fees
27 Sep - 28 Sep
Sleep Inn & Suites Middlesboro
Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers
BBQ/picnic area
Outdoor wedding area
Interior entrance

2. Pine Mountain State Resort Park

Pine Mountain State Resort Park
Pineville
AED 382
AED 421 total
includes taxes & fees
20 Sep - 21 Sep
Pine Mountain State Resort Park
Front of property - evening/night
Fitness facility
1 bedroom, premium bedding, pillowtop beds, in-room safe
Standard Room, 1 King Bed, Accessible (Mobility, Roll-In Shower) | Bathroom | Free toiletries, hair dryer, towels

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.
AED 422
AED 470 total
includes taxes & fees
14 Sep - 15 Sep
Holiday Inn Express Williamsburg by IHG
Coffee/tea maker, fridge, microwave, oven
Exterior detail
TV, DVD player
Terrace/patio

4. Harrogate Home Mountain View’s Dog Friendly

Harrogate Home Mountain View’s Dog Friendly
Harrogate
AED 545
AED 1,068 total
includes taxes & fees
14 Sep - 15 Sep
Harrogate Home Mountain View’s Dog Friendly
Exterior
In-room safe, desk, laptop workspace, blackout drapes
Reception
Free daily continental breakfast

5. Quality Inn Harlan

Quality Inn Harlan
Harlan
AED 344
AED 390 total
includes taxes & fees
20 Sep - 21 Sep
Quality Inn Harlan
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
AED 463
AED 1,129 total
includes taxes & fees
10 Sep - 11 Sep
Peaceful & Private! Pet-friendly Williamsburg Home
Interior
Interior
Interior
Terrace/patio

7. The Highlands Cabin ~ Norris Lake Views & Modern Comfort

The Highlands Cabin ~ Norris Lake Views & Modern Comfort
New Tazewell
AED 479
AED 836 total
includes taxes & fees
10 Sep - 11 Sep
The Highlands Cabin ~ Norris Lake Views & Modern Comfort
Terrace/patio
Coffee/tea maker, fridge, microwave, stovetop
TV, fireplace
2 bedrooms, desk, travel crib, internet

8. Peaceful & Private! Pet-Friendly Williamsburg Home

Peaceful & Private! Pet-Friendly Williamsburg Home
Williamsburg
AED 323
AED 1,142 total
includes taxes & fees
10 Sep - 11 Sep
Peaceful & Private! Pet-Friendly Williamsburg Home
TV, fireplace, books
TV, fireplace, books
Dining
Terrace/patio

9. Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg

Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg
Williamsburg
AED 342
AED 1,271 total
includes taxes & fees
10 Sep - 11 Sep
Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg
Coffee/tea maker, fridge, microwave, oven
TV, fireplace, DVD player, offices
TV, fireplace, DVD player, offices
Shower, hair dryer, towels, shampoo

10. Norris Lake Cabin Getaway, Sleeps 6・View・Fire pit

Norris Lake Cabin Getaway, Sleeps 6・View・Fire pit
New Tazewell
AED 364
AED 1,795 total
includes taxes & fees
4 Oct - 5 Oct
Norris Lake Cabin Getaway, Sleeps 6・View・Fire pit
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

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 3 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.