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Check availability on Middlesboro Family Hotels

Tonight
Feb 27 - Feb 28
Tomorrow
Feb 28 - Mar 1
This weekend
Feb 27 - Mar 1
Next weekend
Mar 6 - Mar 8

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, (827 reviews)
  • cleanliness
    Discover kid-friendly adventures near Cumberland Gap National Historical Park with comfy amenities and free breakfast.
The price is ￥16,020
￥17,990 total
includes taxes & fees
Mar 15 - Mar 16
Sleep Inn & Suites Middlesboro
3 bedrooms, desk, iron/ironing board, travel crib

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 ￥27,277
￥57,736 total
includes taxes & fees
Mar 9 - Mar 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, (1,000 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 ￥17,333
￥19,600 total
includes taxes & fees
Mar 8 - Mar 9
Holiday Inn Express Williamsburg by IHG
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, (684 reviews)
Pine Mountain State Resort Park
Exterior

Quality Inn Harlan

Quality Inn Harlan
2.5 star property
Harlan
8.6 out of 10, Excellent, (345 reviews)
The price is ￥16,133
￥18,299 total
includes taxes & fees
Mar 8 - Mar 9
Quality Inn Harlan
Sundeck

Cumberland Gap Inn

Cumberland Gap Inn
2.5 star property
Cumberland Gap
8.0 out of 10, Very Good, (591 reviews)
The price is ￥15,275
￥17,300 total
includes taxes & fees
Feb 28 - Mar 1
Cumberland Gap Inn
Interior

Calm Country Oasis - Creek, ATV Trls & Norris Lake

Calm Country Oasis - Creek, ATV Trls & Norris Lake
Speedwell
9.4 out of 10, Exceptional, (22 reviews)
The price is ￥17,146
￥40,154 total
includes taxes & fees
Mar 1 - Mar 2
Calm Country Oasis - Creek, ATV Trls & Norris Lake
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 ￥15,275
￥47,844 total
includes taxes & fees
Feb 28 - Mar 1
Peaceful & Private! Pet-friendly Williamsburg Home
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
5.8 out of 10, (796 reviews)
  • cleanliness
    Family fun meets southern charm at the seasonal outdoor pool and mini golf course perfect for creating lifelong memories.
The price is ￥10,599
￥11,797 total
includes taxes & fees
Mar 2 - Mar 3
Super 8 by Wyndham Williamsburg
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, (19 reviews)
The price is ￥11,223
￥24,844 total
includes taxes & fees
Mar 2 - Mar 3
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
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.
View all properties

Choose what matters most at family-friendly hotels in Middlesboro

Breakfast included
Pool

Top Middlesboro Hotel Reviews

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

10/10 Excellent
"Friendly staff, clean hotel, large spacious room, and great breakfast! "
Kasey 1-night trip
Posted 9 days ago
Sleep Inn & Suites Middlesboro

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.