Middlesboro Vacations from $576
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Your Middlesboro Vacation
From its rich history to its spectacular views and beyond, there's a lot to like about Middlesboro. Discover the wonders of this interesting city with a Middlesboro vacation package that's made for you. If taking in sights is on the agenda during your trip to Middlesboro, check out popular attractions like Cumberland Gap National Historical Park, Middlesboro Mall and Bell County Historical Society Museum. Your ideal Middlesboro vacation is just clicks away. Browse accommodations, flights and more on Expedia for an adventure that's tailored to suit your travel style.
The Latest Middlesboro vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Gatlinburg Downtown by IHG
Downtown Gatlinburg
$991
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Knoxville (TYS)
9.6/10 Exceptional! (538 reviews)
Very clean hotel with excellent breakfast including vegetarian options
Reviewed on Aug 16, 2026
Smokies Sanctuary
$1,260
per person
Oct 20 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Knoxville (TYS)
10/10 Exceptional! (1 review)
Beautiful place. Amazing views. I would stay here every time. The property owners were very nice and answered any questions I had. They made sure I was taken care of. If you are in pigeon forge or gatlinburg, stay here.
Reviewed on Jul 17, 2026
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View all tripsStay near popular Middlesboro attractions
Middlesboro Mall
7.6/10 (62 reviews)
This regional shopping center serves as a retail hub for Middlesboro with a mix of national and local stores. Browse fashion, home goods, and dining options in a straightforward, welcoming indoor environment.
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.
Bell County Historical Society Museum
8.2/10 (13 reviews)
Housed in the historic 1915 Dr. J.D. Cawood House, the Bell County Museum preserves Kentucky's regional heritage. Explore artifacts and photographs telling local cultural stories within this National Register landmark.
Middlesboro Hotel Deals
Sleep Inn & Suites Middlesboro
1260 N, 12th Street Middlesboro KY
Fully refundable
$95 nightly
$105 total
Sep 13 - Sep 14
Total with taxes and fees
Holiday Inn Express Middlesboro by IHG
1252 N 12th St Middlesboro KY
Fully refundable
$149 nightly
$164 total
Sep 2 - Sep 3
Total with taxes and fees
9.6/10 Exceptional! (736 reviews)
"The gym is janky and almost scary. It’s very dark and just very isolated. Scary as a female to go to alone. Otherwise nice property. Gym is important to me so I would not stay here again. But I would not discourage someone who isn’t concerned about a gym to stay."
Reviewed on Aug 13, 2026
Econo Lodge Middlesboro
1623 Cumberland Avenue Middlesboro KY
Fully refundable
$87 nightly
$96 total
Sep 13 - Sep 14
Total with taxes and fees
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.
Find the Best Middlesboro Vacation Packages
Middlesboro Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 10,700 |
Max Temp Winter | 45ºF |
Max Temp Summer | 85ºF |
Top Sights | Pine Mountain State Resort Park, Bell County Historical Society Museum and Middlesboro Mall |
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Frequently asked questions
How much does a Middlesboro vacation package cost?
You can snap up a vacation package to this destination from $576 on Expedia. However, how much your vacation 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're looking to book a cheap Middlesboro vacation package, consider visiting in December, January and February. You'll typically find lower rates on hotels and flights during these months — ideal for a budget-friendly getaway.
How many days is enough for Middlesboro?
With a well-organized itinerary, you can easily visit the most popular Middlesboro sights in a few days. But if you want to venture off the beaten track or take day trips, consider booking your Middlesboro vacation for longer.
Is it worth booking a vacation package to Middlesboro?
During your Middlesboro vacation, you can look forward to experiencing some top-notch walking trails and culture. Leave enough room in your schedule to check out leading sights like Cumberland Gap National Historical Park and Middlesboro Mall.
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 vacation package as early as possible.
Is it cheaper to book a Middlesboro vacation as a package?
You can enjoy significant savings on your Middlesboro break by booking a customized vacation 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 vacation 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.
Does Expedia offer Book Now, Pay Later Middlesboro vacation packages?
Jet off on your perfect escape to Middlesboro with help from Expedia's Book Now, Pay Later vacations. No need to save up or wait for your next paycheck — we've joined forces with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans mean you can spread the total cost over 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to budget for your trip and snap up bargains before they disappear.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
