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Check availability on Middlesboro Family Hotels

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, (872 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 AED 370
AED 416 total
includes taxes & fees
31 May - 1 Jun
Sleep Inn & Suites Middlesboro
Exterior detail

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 AED 631
AED 1,303 total
includes taxes & fees
17 May - 18 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, (1,000 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 AED 466
AED 519 total
includes taxes & fees
19 May - 20 May
Holiday Inn Express Williamsburg by IHG
Exterior

Quality Inn Harlan

Quality Inn Harlan
2.5 star property
Harlan
8.6 out of 10, Excellent, (357 reviews)
"I will definitely be back on my family visits."
United States
Heather
The price is AED 359
AED 407 total
includes taxes & fees
14 Jun - 15 Jun
Quality Inn Harlan
Hiking

Pine Mountain State Resort Park

Pine Mountain State Resort Park
3.0 star property
Pineville
9.0 out of 10, Wonderful, (720 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 AED 420
AED 463 total
includes taxes & fees
24 May - 25 May
Pine Mountain State Resort 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 AED 400
AED 964 total
includes taxes & fees
19 May - 20 May
Calm Country Oasis - Creek, ATV Trls & Norris Lake
House (1 Bedroom) | Interior

Peaceful Mountain Cabin w/ Views in Williamsburg

Peaceful Mountain Cabin w/ Views in Williamsburg
2.0 star property
Williamsburg
The price is AED 382
AED 1,337 total
includes taxes & fees
21 May - 22 May
Peaceful Mountain Cabin w/ Views in Williamsburg
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 AED 364
AED 772 total
includes taxes & fees
18 May - 19 May
Cozy Cumberland Gap Cottage Near LMU & Nat’l 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, (827 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 traveler
The price is AED 234
AED 261 total
includes taxes & fees
19 May - 20 May
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, (20 reviews)
"The one positive was being able to get my family together under one roof."
United States
Kade W.
The price is AED 298
AED 623 total
includes taxes & fees
19 May - 20 May
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.
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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

8/10 Good
"The rooms were clean and updated. Conveniently located to the National Park. Great place to stay for a quick one night stay."
Robert 1-night trip
Posted 2 days ago
Sleep Inn & Suites Middlesboro

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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.