Find Family Hotels in Middlesboro, KY

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Check availability on Middlesboro Family Hotels

This weekend
Jun 5 - Jun 7
Next weekend
Jun 12 - Jun 14

Our top choices for Middlesboro family-friendly hotels

In-room safe, desk, laptop workspace, blackout drapes

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro
2.5 star property
Middlesboro
9.2 out of 10, Wonderful, (887 reviews)
  • cleanliness
    Discover kid-friendly adventures near Cumberland Gap National Historical Park with comfy amenities and free breakfast.
The price is ￥17,702
￥19,853 total
includes taxes & fees
Jun 7 - Jun 8
Sleep Inn & Suites Middlesboro
Desk, iron/ironing board, WiFi, bed sheets

Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Middlesboro
9.2 out of 10, Wonderful, (5 reviews)
The price is ￥27,415
￥55,239 total
includes taxes & fees
Jun 9 - Jun 10
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Exterior

Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG
2.5 star property
Williamsburg
9.0 out of 10, Wonderful, (1,004 reviews)
  • cleanliness
    Experience family fun in Williamsburg with an indoor pool, plush beds, and a splash park steps away for endless adventure.
The price is ￥20,953
￥23,320 total
includes taxes & fees
Jun 14 - Jun 15
Holiday Inn Express Williamsburg by IHG
Exterior

Quality Inn Harlan

Quality Inn Harlan
2.5 star property
Harlan
8.6 out of 10, Excellent, (362 reviews)
The price is ￥16,374
￥18,571 total
includes taxes & fees
Jun 24 - Jun 25
Quality Inn Harlan
Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers

Pine Mountain State Resort Park

Pine Mountain State Resort Park
3.0 star property
Pineville
9.0 out of 10, Wonderful, (726 reviews)
The price is ￥23,237
￥25,617 total
includes taxes & fees
Jun 7 - Jun 8
Pine Mountain State Resort Park
Room, 2 Double Beds, Accessible, Non Smoking | Soundproofing, iron/ironing board, free cribs/infant beds, free WiFi

Super 8 by Wyndham Williamsburg

Super 8 by Wyndham Williamsburg
2.5 star property
Williamsburg
5.6 out of 10, (833 reviews)
  • cleanliness
    Family fun meets southern charm at the seasonal outdoor pool and mini golf course perfect for creating lifelong memories.
The price is ￥12,215
￥13,595 total
includes taxes & fees
Jun 18 - Jun 19
Super 8 by Wyndham Williamsburg
House (2 Bedrooms) | Front of property

Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home
3.0 star property
Williamsburg
The price is ￥15,646
￥49,005 total
includes taxes & fees
Jun 14 - Jun 15
Peaceful & Private! Pet-friendly Williamsburg Home
Children's area

Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina

Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
Speedwell
9.4 out of 10, Exceptional, (22 reviews)
The price is ￥14,369
￥28,730 total
includes taxes & fees
Jun 4 - Jun 5
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
Interior

Calm Country Oasis - Creek, ATV Trls & Norris Lake

Calm Country Oasis - Creek, ATV Trls & Norris Lake
Speedwell
9.6 out of 10, Exceptional, (24 reviews)
The price is ￥22,351
￥47,620 total
includes taxes & fees
Jun 4 - Jun 5
Calm Country Oasis - Creek, ATV Trls & Norris Lake
TV, fireplace, books

Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg

Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg
Williamsburg
10.0 out of 10, Exceptional, (1 review)
The price is ￥14,847
￥55,112 total
includes taxes & fees
Jun 4 - Jun 5
Peaceful ‘Mountain Cabin’ w/ Views in 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.
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Choose what matters most at family-friendly hotels in Middlesboro

Breakfast included
Pool

Top Middlesboro Hotel Reviews

Days Inn by Wyndham Jellico - Tennessee State Line

Days Inn by Wyndham Jellico - Tennessee State Line

6/10 Okay
"Never got fresh towels or trash emptied. Bed linens were stained. The rails going up the steps were covered with dry bird crap so there was no way I would touch the rail which made it a hugh fall risk."
Brian 3-night trip
Posted 3 hours ago
Days Inn by Wyndham Jellico - Tennessee State Line

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.