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
14 Sep - 15 Sep
Tomorrow
15 Sep - 16 Sep
This weekend
18 Sep - 20 Sep
Next weekend
25 Sep - 27 Sep

Our top choices for Middlesboro family-friendly hotels

In-room safe, desk, laptop workspace, blackout drapes
Lobby
Lobby
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 393
AED 441 total
includes taxes & fees
27 Sep - 28 Sep
Sleep Inn & Suites Middlesboro
Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers
Outdoor wedding area
Interior entrance
Lobby lounge

2. Pine Mountain State Resort Park

Pine Mountain State Resort Park
Pineville
AED 382
AED 421 total
includes taxes & fees
20 Sep - 21 Sep
Pine Mountain State Resort Park
Front of property - evening/night
Room amenity
1 bedroom, premium bedding, pillowtop beds, in-room safe
Standard Room, 1 King Bed, Accessible (Mobility, Roll-In Shower) | Bathroom | Free toiletries, hair dryer, towels

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 419
AED 466 total
includes taxes & fees
5 Oct - 6 Oct
Holiday Inn Express Williamsburg by IHG
Coffee/tea maker, fridge, microwave, oven
TV, DVD player
Terrace/patio
3 bedrooms, desk, WiFi (free), bed sheets

4. Harrogate Home Mountain View’s Dog Friendly

Harrogate Home Mountain View’s Dog Friendly
Harrogate
AED 536
AED 1,049 total
includes taxes & fees
15 Sep - 16 Sep
Harrogate Home Mountain View’s Dog Friendly
Exterior
Reception
In-room safe, desk, laptop workspace, blackout drapes
Lobby lounge

5. Quality Inn Harlan

Quality Inn Harlan
Harlan
AED 333
AED 378 total
includes taxes & fees
11 Oct - 12 Oct
Quality Inn Harlan
House (2 Bedrooms) | Front of property
House (2 Bedrooms) | Interior
House (2 Bedrooms) | Interior
House (2 Bedrooms) | Interior

6. Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home
Williamsburg
AED 463
AED 1,129 total
includes taxes & fees
15 Sep - 16 Sep
Peaceful & Private! Pet-friendly Williamsburg Home
Terrace/patio
Coffee/tea maker, fridge, microwave, stovetop
TV, fireplace
2 bedrooms, desk, travel crib, internet

7. Peaceful & Private! Pet-Friendly Williamsburg Home

Peaceful & Private! Pet-Friendly Williamsburg Home
Williamsburg
AED 323
AED 1,142 total
includes taxes & fees
15 Sep - 16 Sep
Peaceful & Private! Pet-Friendly Williamsburg Home
Interior
Interior
Terrace/patio
Interior

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

The Highlands Cabin ~ Norris Lake Views & Modern Comfort
New Tazewell
AED 479
AED 829 total
includes taxes & fees
15 Sep - 16 Sep
The Highlands Cabin ~ Norris Lake Views & Modern Comfort
TV, fireplace, books
Dining
TV, fireplace, books
Exterior

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

Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg
Williamsburg
AED 342
AED 1,271 total
includes taxes & fees
15 Sep - 16 Sep
Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg
Children's area
Property grounds
Exterior
Terrace/patio

10. 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 298
AED 623 total
includes taxes & fees
22 Sep - 23 Sep
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
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Choose what matters most at family-friendly hotels in Middlesboro

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Middlesboro Hotel Reviews

Days Inn by Wyndham Jellico - Tennessee State Line

Days Inn by Wyndham Jellico - Tennessee State Line

10/10 Excellent
"Need pool open"
Bobby 2-night trip
Posted 3 days ago
Days Inn by Wyndham Jellico - Tennessee State Line
Quality Inn Harlan

Quality Inn Harlan

8/10 Good
"Clean room, property has been updated, fast several options great place for a quick overnight trip"
Rhett 1-night trip
Posted 8 days ago
Quality Inn Harlan

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.