Middlesboro Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Alexis Wyrick

Top hotels in Middlesboro

Sleep Inn & Suites
Sleep Inn & Suites
2.5 out of 5
1260 N, 12th Street, Middlesboro, KY
Fully refundableReserve now, pay when you stay
The price is 2.798.630 ₫ per night from 13 Jul to 14 Jul
2.798.630 ₫
3.085.210 ₫ total
13 Jul - 14 Jul
includes taxes & fees
9/10 Wonderful! (735 reviews)
"Weekend stay for nearby music festival. Staff friendly & room clean & roomy."

Reviewed on 17 Jun 2025

Sleep Inn & Suites
Holiday Inn Express Middlesboro by IHG
Holiday Inn Express Middlesboro by IHG
2.5 out of 5
1252 N 12th St, Middlesboro, KY
Fully refundable
The price is 3.292.506 ₫ per night from 6 Jul to 7 Jul
3.292.506 ₫
3.629.596 ₫ total
6 Jul - 7 Jul
includes taxes & fees
9.4/10 Exceptional! (654 reviews)
"We had no issues staying at this property."

Reviewed on 13 Jun 2025

Holiday Inn Express Middlesboro by IHG
Econo Lodge Middlesboro
Econo Lodge Middlesboro
2 out of 5
1623 Cumberland Avenue, Middlesboro, KY
Fully refundableReserve now, pay when you stay
The price is 2.234.201 ₫ per night from 6 Jul to 7 Jul
2.234.201 ₫
2.462.983 ₫ total
6 Jul - 7 Jul
includes taxes & fees
7/10 Good! (396 reviews)
"There for a 4 day trip with friends, staff was great and the room was clean and comfy! Ive stayed here on this trip the past 5 years and its always great."

Reviewed on 16 Jun 2025

Econo Lodge Middlesboro
See all 322 properties in Middlesboro
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.

Frequently asked questions

How much does a Middlesboro holiday package cost?
You can snap up a holiday package to this destination on Expedia. However, how much your holiday to Middlesboro costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Middlesboro?
If you'd like to snag a cheap Middlesboro holiday package, consider travelling in January, February and November. You'll usually find better rates on airfares and hotels during these months --- ideal for travellers wishing to save money.
How many days is enough for Middlesboro?
Generally, a handful of days is enough to explore the top attractions during your Middlesboro holiday. However, if you want to have some time to rest or take day tours, think about extending your trip.
How to find the best Middlesboro package deals?
Use Expedia's handy filters to help you find some of the best Middlesboro package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Middlesboro package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your holiday package as early as possible.
Is it cheaper to book a Middlesboro holiday as a package?
You can enjoy significant savings on your Middlesboro break by booking a customised holiday package. Click on the "Package" heading, then enter your travel dates and destination to view some great hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday package to Middlesboro?
If you're planning an impromptu Middlesboro trip, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can score terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Middlesboro?

  1. Choose the ideal time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to visit Middlesboro.
  2. Calculate your budget: Ensure you have enough money to cover everything from dining out and transportation to activities and flights. Your accommodation will likely be the biggest expense during your trip to Middlesboro.
  3. Work out your trip length: Consider how much time you'd like to spend discovering Middlesboro. Plan your days so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Middlesboro holiday package.

Popular places to visit

Middlesboro Country Club

Enjoy a round of golf in Middlesboro at Middlesboro Country Club. Discover the mountain views while you're in the area.

Middlesboro Country Club

Bell County Historical Society Museum

You can spend an afternoon studying the exhibits at Bell County Historical Society Museum during your trip to Middlesboro. Discover the mountain views while you're in the area.

Bell County Historical Society Museum