Middlesboro Hotel Guide - Family Friendly Hotels in Middlesboro, Kentucky

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Check availability on Middlesboro Family Friendly Hotels

Next weekend
29 May - 31 May
In two weeks
5 Jun - 7 Jun

Our top choices for Middlesboro family-friendly hotels

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

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro
2.5 star property
Middlesboro
9.2 out of 10, Wonderful, (877 reviews)
  • cleanliness
    Discover kid-friendly adventures near Cumberland Gap National Historical Park with comfy amenities and free breakfast.
"Nice hotel. Very comfortable stay."
United States
Adrienne
The price is €102
includes taxes & fees
22 Jun - 23 Jun
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)
"We enjoyed our stay. "
United States
Emily S.
The price is €304
includes taxes & fees
25 May - 26 May
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, (1,002 reviews)
  • cleanliness
    Experience family fun in Williamsburg with an indoor pool, plush beds, and a splash park steps away for endless adventure.
"The check in was easy with my Expedia reservation but there was a $20 charge I wasn’t told about until check in. The room was ready and clean. The pool had just been cleaned and was perfect for my husband and I. The staff was friendly and the coffee was hot!!"
United States
Jennifer
The price is €125
includes taxes & fees
4 Jun - 5 Jun
Holiday Inn Express Williamsburg by IHG
Exterior

Quality Inn Harlan

Quality Inn Harlan
2.5 star property
Harlan
8.6 out of 10, Excellent, (359 reviews)
"I will definitely be back on my family visits."
United States
Heather
The price is €93
includes taxes & fees
14 Jun - 15 Jun
Quality Inn Harlan
Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, pool loungers

Pine Mountain State Resort Park

Pine Mountain State Resort Park
3.0 star property
Pineville
9.0 out of 10, Wonderful, (724 reviews)
"First time ever staying here at the Lodge. Was a long time resident for over 12 years and I always wanted to come here and just stay for the night and have dinner. Sooo happy that now that when I travel back home to visit family and friends that I can now have a place that I can stay and get away from the hustle of the big city life. Love My Mountain Home! "
United States
Paulette
The price is €138
includes taxes & fees
25 May - 26 May
Pine Mountain State Resort Park
Exterior

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Cumberland Gap
9.2 out of 10, Wonderful, (46 reviews)
"We hiked up to Tri-State Peak and had a fun time just being together with family."
United States
Denise S.
The price is €185
includes taxes & fees
26 May - 27 May
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
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)
"Would love to stay again with family and friends next time"
United States
Sam H.
The price is €251
includes taxes & fees
31 May - 1 Jun
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 €265
includes taxes & fees
25 May - 26 May
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, (20 reviews)
"The one positive was being able to get my family together under one roof."
United States
Kade W.
The price is €159
includes taxes & fees
26 May - 27 May
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
Room, 2 Double Beds, Accessible, Non Smoking

Super 8 by Wyndham Williamsburg

Super 8 by Wyndham Williamsburg
2.5 star property
Williamsburg
5.6 out of 10, (829 reviews)
  • cleanliness
    Family fun meets southern charm at the seasonal outdoor pool and mini golf course perfect for creating lifelong memories.
"First room smelled like sewer so had to switch. Next room was dirty and had to be cleaned before use. Hotel ran out of towels and toilet paper. One room in our groups door didnt lock so anyone could walk in. Positives were they let us use the pool and hr later for a bday and the rooms were updated but still need some care."
United States
Anonymous traveller
The price is €65
includes taxes & fees
27 May - 28 May
Super 8 by Wyndham 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.
View all properties

Choose what matters most at family-friendly hotels in Middlesboro

Breakfast included
Pool

Top Middlesboro Hotel Reviews

Super 8 by Wyndham Williamsburg

Super 8 by Wyndham Williamsburg

4/10 Poor
"Cobwebs all over ceiling and walls. Some kind of liquid on the floor that is bubbled up and dried, reddish brown. Sink drained slowly, bathroom smells like sewer. At least this time the owner didn't peek in the windows!"
Trish 1-night trip
Posted 17 hours ago
Super 8 by Wyndham Williamsburg

Frequently asked questions

What's Middlesboro like for family-friendly holidays?
The destination of Middlesboro is a great choice if you've been thinking about a holiday with your children. The wildlife, glaciers and mountain views are just a few things that make this an attractive spot for a family holiday.
What's the best family accommodation 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 holiday in Middlesboro?
The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 5°C. Average annual precipitation for Middlesboro is 1581 mm.
What's there to see and do with your family in Middlesboro?
Middlesboro Mall and Bell County Public Library Pineville Branch are interesting attractions that you and your family may enjoy exploring while you are staying in Middlesboro. Make sure that you have lots of time for activities such as Kentucky Ridge State Forest and C.W. Gose Municipal Park.