Middlesboro Holidays

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Your Middlesboro Holiday

With a reputation for its rich history and spectacular views, Middlesboro is a fabulous getaway destination. Lock in one of our Middlesboro holiday packages and enjoy all that this lively city has to offer. Make your trip to Middlesboro even more enjoyable by going sightseeing. Cumberland Gap National Historical Park, Middlesboro Mall and Bell County Historical Society Museum are among the top attractions you'll want to explore. No matter your travel plans or budget, organising a tailored Middlesboro holiday is easy with Expedia.

Middlesboro Holiday

Middlesboro Essential Information

Language
English
Currency
U.S dollars
Population
10,700
Max Temp Winter
7ºC
Max Temp Summer
29ºC
Top Sights
Pine Mountain State Resort Park, Bell County Historical Society Museum and Middlesboro Mall

Our pick of the best Middlesboro Hotel Deals

Sleep Inn & Suites
Sleep Inn & Suites
2.5 out of 5
1260 N, 12th Street, Middlesboro, KY
The price is AU$163 per night from 23 Feb to 24 Feb
AU$163
includes taxes & fees
23 Feb - 24 Feb
9/10 Wonderful! (685 reviews)
"Saw (and smelled) a few fragrance plugins, no hotel should have these. I unplugged the one in my room."

Reviewed on 27 Jan. 2025

Sleep Inn & Suites
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 AU$143 per night from 16 Feb to 17 Feb
AU$143
includes taxes & fees
16 Feb - 17 Feb
6.8/10 (361 reviews)
"Rooms are always very clean the people at the desk are always nice love staying here!!"

Reviewed on 8 Feb. 2025

Econo Lodge Middlesboro
Holiday Inn Express Williamsburg, an IHG Hotel
Holiday Inn Express Williamsburg, an IHG Hotel
2.5 out of 5
56 West Highway 92, Williamsburg, KY
Fully refundable
The price is AU$207 per night from 23 Feb to 24 Feb
AU$207
includes taxes & fees
23 Feb - 24 Feb
9/10 Wonderful! (893 reviews)
"Extremely kind staffs!"

Reviewed on 7 Feb. 2025

Holiday Inn Express Williamsburg, an IHG Hotel
See all 318 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.