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
24 Sep - 25 Sep
Tomorrow
25 Sep - 26 Sep
This weekend
25 Sep - 27 Sep
Next weekend
2 Oct - 4 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
18 Oct - 19 Oct
Sleep Inn & Suites Middlesboro
Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers
Interior entrance
Lobby lounge
BBQ/picnic 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
Standard Room, 1 King Bed, Accessible (Mobility, Roll-In Shower) | Bathroom | Free toiletries, hair dryer, towels
1 bedroom, premium bedding, pillowtop beds, in-room safe

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
20 Oct - 21 Oct
Holiday Inn Express Williamsburg by IHG
Exterior
Lobby lounge
Free daily continental breakfast
In-room safe, desk, laptop workspace, blackout drapes

4. Quality Inn Harlan

Quality Inn Harlan
Harlan
AED 320
AED 363 total
includes taxes & fees
18 Oct - 19 Oct
Quality Inn Harlan
Exterior
TV, books, offices
2 bedrooms, desk, iron/ironing board, WiFi (free)
Dining

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

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Cumberland Gap
AED 474
AED 890 total
includes taxes & fees
27 Sep - 28 Sep
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Coffee/tea maker, fridge, microwave, oven
Exterior detail
TV, DVD player
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
27 Sep - 28 Sep
Harrogate Home Mountain View’s Dog Friendly
Interior
Property grounds
Exterior
Interior

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

Calm Country Oasis - Creek, ATV Trls & Norris Lake
Speedwell
AED 400
AED 949 total
includes taxes & fees
28 Sep - 29 Sep
Calm Country Oasis - Creek, ATV Trls & Norris Lake
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
28 Sep - 29 Sep
The Highlands Cabin ~ Norris Lake Views & Modern Comfort
House (2 Bedrooms) | Front of property
House (2 Bedrooms) | Interior
House (2 Bedrooms) | Interior
House (2 Bedrooms) | Interior

9. Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home
Williamsburg
AED 463
AED 1,129 total
includes taxes & fees
25 Sep - 26 Sep
Peaceful & Private! Pet-friendly Williamsburg Home
Terrace/patio
2 bedrooms, desk, travel crib, internet
TV, fireplace
Coffee/tea maker, fridge, microwave, stovetop

10. Peaceful & Private! Pet-Friendly Williamsburg Home

Peaceful & Private! Pet-Friendly Williamsburg Home
Williamsburg
AED 323
AED 1,142 total
includes taxes & fees
25 Sep - 26 Sep
Peaceful & Private! Pet-Friendly Williamsburg Home
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 3 days ago
Quality Inn
Quality Inn Harlan

Quality Inn Harlan

10/10 Excellent
"Rooms nice and clean staff was wonderful as always. Enjoyed our stay. Will come back again"
Jan 2-night trip
Posted 6 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.