An aerial view of a town surrounded by mountains, with a mix of residential and commercial buildings, and a highway running through the center.

Family Hotels & Resorts in Middlesboro

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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 curtains

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro
2.5 star property
Middlesboro
9.2 out of 10, Wonderful, (902 reviews)
  • cleanliness
    Discover kid-friendly adventures near Cumberland Gap National Historical Park with comfy amenities and free breakfast.
The price is AU$169
includes taxes & fees
17 Aug - 18 Aug
Sleep Inn & Suites Middlesboro
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 price is AU$153
includes taxes & fees
10 Aug - 11 Aug
Holiday Inn Express Williamsburg by IHG
Exterior

Quality Inn Harlan

Quality Inn Harlan
2.5 star property
Harlan
8.6 out of 10, Excellent, (372 reviews)
The price is AU$162
includes taxes & fees
13 Aug - 14 Aug
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, (735 reviews)
The price is AU$241
includes taxes & fees
24 July - 25 July
Pine Mountain State Resort Park
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 AU$439
includes taxes & fees
29 July - 30 July
Peaceful & Private! Pet-friendly Williamsburg Home
Exterior

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Cumberland Gap
9.4 out of 10, Exceptional, (48 reviews)
The price is AU$401
includes taxes & fees
21 July - 22 July
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
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 AU$491
includes taxes & fees
18 July - 19 July
Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg
Terrace/patio

Peaceful & Private! Pet-Friendly Williamsburg Home

Peaceful & Private! Pet-Friendly Williamsburg Home
Williamsburg
10.0 out of 10, Exceptional, (3 reviews)
The price is AU$435
includes taxes & fees
29 July - 30 July
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
9.2 out of 10, Wonderful, (23 reviews)
The price is AU$260
includes taxes & fees
21 July - 22 July
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
Interior

The Highlands Cabin ~ Norris Lake Views & Modern Comfort

The Highlands Cabin ~ Norris Lake Views & Modern Comfort
New Tazewell
10.0 out of 10, Exceptional, (4 reviews)
The price is AU$330
includes taxes & fees
23 July - 24 July
The Highlands Cabin ~ Norris Lake Views & Modern Comfort
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

Lake Front 2-Bedroom Home W/ Privacy! Beautiful Views & Numerous Amenities...

Lake Front 2-Bedroom Home W/ Privacy! Beautiful Views & Numerous Amenities...

10/10 Excellent
"Very beautiful lake house with a sliver of lake to gaze at from the big back deck with plenty of seating. Two nice bedrooms sized bedrooms with a bathroom for each. Great kitchen and plenty of seating in the living room. Good, easy communication with the owner. Would stay there again."
jeff 7-night trip
Posted 5 days ago
Lake Front 2-Bedroom Home W/ Privacy! Beautiful Views & Numerous Amenities...

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 The Pinnacle.