Middlesboro Vacations from $403
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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.
River Terrace Resort & Convention Center
Downtown Gatlinburg
$403
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Knoxville (TYS)
7.8/10 Good! (1,024 reviews)
Staff was professional, quick and informative. Room was clean, beds comfortable. View from room was cute, continental breakfast. Parking was sufficient considering we stayed during Jeep week.
Close to many restaurants, shops and the aquarium. 10 or so minute walk to all amenities.
Very pleased with the experience. Would book again.
Reviewed on Aug 26, 2026
Laurel Point Resort
Chalet Village
$730
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Knoxville (TYS)
9/10 Wonderful! (339 reviews)
We love the location of this place, just outside the downtown madness, in a beautiful spot on the hill. Having 2 bedrooms and 2 bathrooms is very convenient, even with just 2 of us. the full kitchen let us make meals without spending a fortune, as well as having evening snacks, and packing food for daily excursions. very nice all around.
the unit we were in had a huge jacuzzi tub, but a very small shower. no problem, we just used the bigger guest shower.
The staff was very friendly and helpful, and after hours checkin was great!
Reviewed on Aug 27, 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
Holiday Inn Express Middlesboro by IHG
1252 N 12th St Middlesboro KY
$131 nightly
$144 total
Aug 30 - Aug 31
Total with taxes and fees
Sleep Inn & Suites Middlesboro
1260 N, 12th Street Middlesboro KY
Fully refundable
$111 nightly
$122 total
Sep 8 - Sep 9
Total with taxes and fees
9.2/10 Wonderful! (922 reviews)
"Very friendly staff, great location. Perfect for our family trip."
Reviewed on Aug 27, 2026
Econo Lodge Middlesboro
1623 Cumberland Avenue Middlesboro KY
Fully refundable
$80 nightly
$88 total
Sep 6 - Sep 7
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 $403 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.