Middlesboro Vacations from $344
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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
$650
per person
Dec 28 - Jan 1
found 9 hours ago
Roundtrip flight included
Orlando (MCO) to Knoxville (TYS)
7.8/10 Good! (1,013 reviews)
Outdated and not very clean however the location was perfect! Also they try and sell you a tour when you first arrive which was annoying. Just trying to check in not listen to a whole selling pitch!
Reviewed on Oct 13, 2026
The Copper Bird Cabin
$579
per person
Jan 7 - Jan 11
found 24 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Knoxville (TYS)
10/10 Exceptional! (4 reviews)
Great place located close to all entertainment tou wont be disappointed with your stay. I will be back.
Reviewed on Sep 20, 2026
Reagan Resorts Inn
Downtown Gatlinburg
$716
per person
Dec 23 - Dec 27
found 18 hours ago
Roundtrip flight included
Dallas (DFW) to Knoxville (TYS)
8.6/10 Excellent! (1,752 reviews)
I booked this hotel because it had a balcony. I didn’t care if the balcony had a city view or a mountain view. Our balcony had neither. There was a wall right in front of the balcony with barely any sunlight coming through. Very disappointing!
Reviewed on Oct 11, 2026
Smokies Sanctuary
$578
per person
Jan 5 - Jan 8
found 1 day ago
Roundtrip flight included
Miami (MIA) 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
$112 nightly
$123 total
Nov 8 - Nov 9
Total with taxes and fees
Econo Lodge Middlesboro
1623 Cumberland Avenue Middlesboro KY
Fully refundable
$85 nightly
$93 total
Oct 21 - Oct 22
Total with taxes and fees
7.4/10 Good! (505 reviews)
"Bathroom fan sounds like a 747 taking off. When you flushed the toilet it squealed for at least 60seconds. Turned on the bathroom faucet and it was so loud my wife couldn’t hear me over it. And it came out so hard it knocked the glass out of my hand."
Reviewed on Oct 13, 2026
Suburban Studios Middlesboro
1623 Cumberland Avenue Building B Middlesboro KY
Fully refundableReserve now, pay when you stay
$74 nightly
$81 total
Nov 4 - Nov 5
Total with taxes and fees
8.2/10 Very Good! (111 reviews)
"It was just a stop in our travels for an quick overnight stay. Very reasonable. Staff super kind and friendly. Rooms were clean. But the place could use an update. Cont"
Reviewed on Oct 12, 2026
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 $344 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.
