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

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Check availability on Middlesboro Family Hotels

Tonight
28 Sep - 29 Sep
Tomorrow
29 Sep - 30 Sep
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Middlesboro family-friendly hotels

In-room safe, desk, laptop workspace, blackout drapes
Lobby
Free buffet breakfast
Exterior

1. Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro
Middlesboro
  • Discover kid-friendly adventures near Cumberland Gap National Historical Park with comfy amenities and free breakfast.
AED 403
AED 452 total
includes taxes & fees
25 Oct - 26 Oct
Sleep Inn & Suites Middlesboro
Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers
BBQ/picnic area
Lobby lounge
Outdoor wedding area

2. Pine Mountain State Resort Park

Pine Mountain State Resort Park
Pineville
AED 441
AED 486 total
includes taxes & fees
4 Oct - 5 Oct
Pine Mountain State Resort Park
Front of property - evening/night
Fitness facility
1 bedroom, premium bedding, pillowtop beds, in-room safe
Room amenity

3. Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG
Williamsburg
  • Experience family fun in Williamsburg with an indoor pool, plush beds, and a splash park steps away for endless adventure.
AED 433
AED 482 total
includes taxes & fees
13 Oct - 14 Oct
Holiday Inn Express Williamsburg by IHG
Exterior
2 bedrooms, desk, iron/ironing board, WiFi (free)
Coffee/tea maker, fridge, microwave, oven
Dining

4. Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Cumberland Gap
AED 474
AED 897 total
includes taxes & fees
29 Sep - 30 Sep
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Interior
Property grounds
Exterior
Dining

5. Calm Country Oasis - Creek, ATV Trls & Norris Lake

Calm Country Oasis - Creek, ATV Trls & Norris Lake
Speedwell
AED 400
AED 931 total
includes taxes & fees
19 Oct - 20 Oct
Calm Country Oasis - Creek, ATV Trls & Norris Lake
Coffee/tea maker, fridge, microwave, oven
TV, DVD player
Terrace/patio
3 bedrooms, desk, WiFi (free), bed sheets

6. Harrogate Home Mountain View’s Dog Friendly

Harrogate Home Mountain View’s Dog Friendly
Harrogate
AED 496
AED 970 total
includes taxes & fees
29 Sep - 30 Sep
Harrogate Home Mountain View’s Dog Friendly
Exterior
Free daily continental breakfast
Reception
In-room safe, desk, laptop workspace, blackout drapes

7. Quality Inn Harlan

Quality Inn Harlan
Harlan
AED 325
AED 368 total
includes taxes & fees
25 Oct - 26 Oct
Quality Inn Harlan
Children's area
Property grounds
Dining
Terrace/patio

8. 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
AED 314
AED 642 total
includes taxes & fees
29 Sep - 30 Sep
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
TV, fireplace, books
Dining
TV, fireplace, books
Terrace/patio

9. Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg

Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg
Williamsburg
AED 342
AED 1,207 total
includes taxes & fees
29 Sep - 30 Sep
Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg
Interior
Interior
Interior
Interior

10. The Highlands Cabin ~ Norris Lake Views & Modern Comfort

The Highlands Cabin ~ Norris Lake Views & Modern Comfort
New Tazewell
AED 479
AED 818 total
includes taxes & fees
29 Sep - 30 Sep
The Highlands Cabin ~ Norris Lake Views & Modern Comfort
View all properties

Choose what matters most at family-friendly hotels in Middlesboro

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Middlesboro Hotel Reviews

Quality Inn

Quality Inn

10/10 Excellent
"Very helpful staff and clean, well kept rooms."
Dennis 2-night trip
Posted 6 days ago
Quality Inn

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.