Middlesboro Holidays

Photo by Alexis Wyrick

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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 S$151 per night from 1 Sept to 2 Sept
S$151
1 Sept - 2 Sept
includes taxes & fees
9/10 Wonderful! (757 reviews)
"The hotel is off the main road and was so quiet despite being fully booked. The staff was so incredibly friendly. I loved my stay here!"

Reviewed on 25 Jul, 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 S$134 per night from 17 Aug to 18 Aug
S$134
17 Aug - 18 Aug
includes taxes & fees
7/10 Good! (420 reviews)
"The exterior has a very dreary, look and feeling. However, the interior was very clean and comfortable. The registration staff was very welcoming and accommodating which made up for the older, not so inviting exterior."

Reviewed on 1 Aug, 2025

Econo Lodge Middlesboro
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 S$168 per night from 1 Sept to 2 Sept
S$168
1 Sept - 2 Sept
includes taxes & fees
9.4/10 Exceptional! (670 reviews)
"Bed was amazingly comfortable..continental breakfast with great options.. staff very friendly and helpful."

Reviewed on 31 Jul, 2025

Holiday Inn Express Middlesboro by IHG
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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.