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Find Family Hotels in Middlesboro, KY

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Check availability on Middlesboro Family Hotels

Tonight
Dec 4 - Dec 5
Tomorrow
Dec 5 - Dec 6
This weekend
Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

Top Middlesboro Family Hotels

Exterior
Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

2.5 star property
Middlesboro
9.2 out of 10, Wonderful, (812)
"The breakfast was great and customer service was great! Very clean and beautiful views "
United States
Solange
The price is NT$2,928
NT$3,228 total
includes taxes & fees
Dec 28 - Dec 29
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, (1001)
"We really enjoyed our stay! "
United States
Andrea Strode
The price is NT$3,107
NT$3,513 total
includes taxes & fees
Dec 17 - Dec 18
Holiday Inn Express Williamsburg by IHG
Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers
Pine Mountain State Resort Park

Pine Mountain State Resort Park

3.0 star property
Pineville
9.0 out of 10, Wonderful, (667)
"Great views, and wonderful trails, and pet-friendly."
United States
Frederick
The price is NT$3,506
NT$3,865 total
includes taxes & fees
Dec 5 - Dec 6
Pine Mountain State Resort Park
Exterior
Quality Inn

Quality Inn

2.5 star property
Harlan
8.6 out of 10, Excellent, (335)
"Room was nice and clean, staff very courteous, breakfast very good."
United States
Gary
The price is NT$2,821
NT$3,200 total
includes taxes & fees
Jan 1 - 2026/1/2
Quality Inn
Honeymoon Suite, 1 King Bed | Laptop workspace, free WiFi, bed sheets
Cumberland Gap Inn

Cumberland Gap Inn

2.5 star property
Cumberland Gap
8.0 out of 10, Very Good, (583)
"The views around the area are beautiful and the town is peaceful and quiet "
United States
Robert
The price is NT$3,069
NT$3,476 total
includes taxes & fees
Dec 5 - Dec 6
Cumberland Gap Inn
Exterior
Super 8 by Wyndham Williamsburg

Super 8 by Wyndham Williamsburg

2.5 star property
Williamsburg
5.8 out of 10, (765)
"Price was right room was clean. Many choices to eat. Staff was pleasant. "
United States
Susan
The price is NT$1,810
NT$2,015 total
includes taxes & fees
Dec 9 - Dec 10
Super 8 by Wyndham Williamsburg
House (2 Bedrooms) | Interior
Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home

3.0 star property
Williamsburg
The price is NT$3,069
NT$9,613 total
includes taxes & fees
Dec 7 - Dec 8
Peaceful & Private! Pet-friendly Williamsburg Home
Exterior
Rodeway Inn

Rodeway Inn

2.0 star property
Harlan
5.6 out of 10, (231)
"Clean and staff was good The bathroom is putting out a bad smell like it was from the septic and we tried three different microwaves that did not work that was my only complaint"
United States
Mike
The price is NT$1,628
NT$1,846 total
includes taxes & fees
Dec 14 - Dec 15
Rodeway Inn
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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Top Middlesboro Hotel Reviews

Quality Inn

Quality Inn

10/10 Excellent
"It was short stay met our needs "
Karen 1-night trip
Posted 2 days ago
Quality Inn

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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 The Pinnacle.