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Family Hotels & Resorts in Middlesboro from NZ$113

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Our top choices for Middlesboro family-friendly hotels

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro
2.5 star property
Middlesboro
9.2 out of 10, Wonderful, (815)
"Room was clean and comfortable. Staff was courteous. "
United States
Tommy
The price is NZ$177
includes taxes & fees
25 Jan - 26 Jan 2026
Sleep Inn & Suites Middlesboro

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)
"We enjoyed our stay. "
United States
Emily S.
The price is NZ$635
includes taxes & fees
30 Dec - 31 Dec
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG
2.5 star property
Williamsburg
9.0 out of 10, Wonderful, (1004)
"Staff was nice and breakfast was good"
United States
nicole
The price is NZ$223
includes taxes & fees
13 Jan - 14 Jan 2026
Holiday Inn Express Williamsburg by IHG

Quality Inn Harlan

Quality Inn Harlan
2.5 star property
Harlan
8.6 out of 10, Excellent, (340)
"Room was nice and clean, staff very courteous, breakfast very good."
United States
Gary
The price is NZ$173
includes taxes & fees
9 Jan - 10 Jan 2026
Quality Inn Harlan

Pine Mountain State Resort Park

Pine Mountain State Resort Park
3.0 star property
Pineville
9.0 out of 10, Wonderful, (673)
"Great place to stay!"
United States
William
The price is NZ$242
includes taxes & fees
2 Jan - 3 Jan 2026
Pine Mountain State Resort Park

Cumberland Gap Inn

Cumberland Gap Inn
2.5 star property
Cumberland Gap
8.0 out of 10, Very good, (585)
"Clean love the people we always stay there when we travel south"
United States
Christopher
The price is NZ$190
includes taxes & fees
30 Dec - 31 Dec
Cumberland Gap Inn

Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home
3.0 star property
Williamsburg
The price is NZ$526
includes taxes & fees
30 Dec - 31 Dec
Peaceful & Private! Pet-friendly Williamsburg Home

The Highlands Cabin Retreat at Norris Lake

The Highlands Cabin Retreat at Norris Lake
2.0 star property
New Tazewell
10.0 out of 10, Exceptional, (1)
"The cabin was clean, cozy, and overall amazing! "
United States
Fannie
The price is NZ$354
includes taxes & fees
4 Jan - 5 Jan 2026
The Highlands Cabin Retreat at Norris Lake

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, (19)
"It was exceptional "
United States
Dennis W.
The price is NZ$273
includes taxes & fees
1 Jan - 2 Jan 2026
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina

Super 8 by Wyndham Williamsburg

Super 8 by Wyndham Williamsburg
2.5 star property
Williamsburg
5.8 out of 10, (774)
"Price was right room was clean. Many choices to eat. Staff was pleasant. "
United States
Susan
The price is NZ$113
includes taxes & fees
11 Jan - 12 Jan 2026
Super 8 by Wyndham Williamsburg
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.

Top Middlesboro Hotel Reviews

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.