Middlesboro Vacations

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Find the Best Middlesboro Vacation Packages

Middlesboro Hotel Deals

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

2.5 out of 5
1260 N, 12th Street Middlesboro KY
Fully refundable
The price is AEDĀ 372 per night from Aug 9 to Aug 10
AEDĀ 372
AEDĀ 417 total
9 Aug - 10 Aug
includes taxes & fees
Sleep Inn & Suites Middlesboro
Econo Lodge Middlesboro

Econo Lodge Middlesboro

2 out of 5
1623 Cumberland Avenue Middlesboro KY
Fully refundable
The price is AEDĀ 327 per night from Jul 29 to Jul 30
AEDĀ 327
AEDĀ 361 total
29 Jul - 30 Jul
includes taxes & fees
7.4/10 Good! (491 reviews)
"Rooms were clean, thankfully AC worked because we were hot and sweaty from moving my daughter into her apartment. Bathrooms were clean as well as the room."

Reviewed on 12 July 2026

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 AEDĀ 405 per night from Aug 2 to Aug 3
AEDĀ 405
AEDĀ 446 total
2 Aug - 3 Aug
includes taxes & fees
9.6/10 Exceptional! (727 reviews)
"We checked in around 8pm and were greeted by the front desk staff was fantastic. They interacted with my 11-year-old great-niece in the best way. Sharing jokes and talking to her directly on her level. Of course, the adults felt comfortable and welcome as well. The pool was very nice and clean. The ..."

Reviewed on 27 June 2026

Holiday Inn Express Middlesboro by IHG
See all 361 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.
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Frequently asked questions

How much does a Middlesboro vacation package cost?
You'll find cheap prices on Expedia for your Middlesboro getaway. However, factors like the hotel choice, length of stay and season will influence how much your vacation to Middlesboro costs.
What are the cheapest months to go to Middlesboro?
You can usually find reduced prices and better availability in January, February and November. Check out our cheap Middlesboro vacation packages and you could score some excellent off-season deals.
How to find the best Middlesboro package deals?
Start your search for a Middlesboro package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Middlesboro package deal right away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Middlesboro adventure off to a flying start.
Is it cheaper to book a Middlesboro vacation as a package?
You can enjoy significant savings on your next Middlesboro break by booking a personalized vacation package. Check the "Package" heading, then select your travel dates and destination to browse some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Middlesboro?
Enjoy incredible discounts by reserving your flights early with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Middlesboro break.
How to plan a trip to Middlesboro?

  1. Choose your dates: The things you want to do in Middlesboro and your favorite season will help you decide when to go.
  2. Set a budget: Factor in expenses like flights, transportation and food when working out how much to set aside for your trip to Middlesboro. Then, select a hotel that works with your budget, whether that's a wallet-friendly option or a more upscale retreat.
  3. Decide how many days away: Start by compiling a list of the sights and activities you'd like to experience in Middlesboro. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your airfare and accommodations: After you've nailed down your dates and duration, book the ideal Middlesboro vacation package for you.