Middlesboro Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Middlesboro

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

2.5 out of 5
1260 N, 12th Street Middlesboro KY
Fully refundable
The price is S$135 per night from 1 Dec to 2 Dec
S$135
1 Dec - 2 Dec
includes taxes & fees
9.2/10 Wonderful! (958 reviews)
"Very friendly staff"

Reviewed on 8 Nov, 2026

Sleep Inn & Suites Middlesboro
Econo Lodge Middlesboro

Econo Lodge Middlesboro

2 out of 5
1623 Cumberland Avenue Middlesboro KY
Fully refundable
The price is S$113 per night from 22 Nov to 23 Nov
S$113
22 Nov - 23 Nov
includes taxes & fees
7.4/10 Good! (511 reviews)
"Soon as we arrived, we were met by Susan who worked inside. ..so friendly ,helpful ,..such a warm welcoming and that’s the beginning of an awesome stay ..we made coffeees (delicious) and she gave us some snacks ..room was awesome and clean as a whistle ..breakfast was delicious ..just go you won’t ..."

Reviewed on 4 Nov, 2026

Econo Lodge Middlesboro
Suburban Studios Middlesboro

Suburban Studios Middlesboro

2 out of 5
1623 Cumberland Avenue Building B Middlesboro KY
Fully refundableReserve now, pay when you stay
The price is S$102 per night from 5 Dec to 6 Dec
S$102
5 Dec - 6 Dec
includes taxes & fees
8.4/10 Very good! (123 reviews)
"Not well insulated and neighbors & dogs very loud."

Reviewed on 9 Nov, 2026

Suburban Studios Middlesboro
See all 356 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.

Stay near popular Middlesboro attractions

Middlesboro Country Club

Established in 1889, Middlesboro Country Club is America's oldest continuously played nine-hole golf course. Challenge yourself on undulating greens while surrounded by breathtaking Appalachian Mountain vistas.
See properties

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.