Middlesboro Vacations from $321

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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.
Club Wyndham Resort at Fairfield Glade

Club Wyndham Resort at Fairfield Glade

3.5 out of 5
Save 100% on your flight
Price was $451, price is now $321 per person
$321
per person
Oct 19 - Oct 23
found 6 hours ago
Roundtrip flight included
Miami (MIA) to Knoxville (TYS)
9.2/10 Wonderful! (359 reviews)
I did not like the fact that they attempted to sign you up for a "sales" spill for the property. I don't like timeshare or sales pitches.

Reviewed on Aug 11, 2025

Wild Bear Inn

Wild Bear Inn

3 out of 5
Save 100% on your flight
Price was $592, price is now $360 per person
$360
per person
Oct 17 - Oct 19
found 18 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Knoxville (TYS)
7.8/10 Good! (1,007 reviews)
Was much nicer than i thought it would be. Pillows were amazing! We slept great. Staff were amazing! We will stay again!

Reviewed on Aug 10, 2025

Courtyard by Marriott Gatlinburg Downtown

Courtyard by Marriott Gatlinburg Downtown

3 out of 5
Save 100% on your flight
Price was $711, price is now $455 per person
$455
per person
Nov 1 - Nov 5
found 12 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Knoxville (TYS)
9/10 Wonderful! (1,001 reviews)
Nice place watch out for bears ....

Reviewed on Aug 22, 2025

The Ramsey Hotel & Convention Center

The Ramsey Hotel & Convention Center

3 out of 5
Downtown Pigeon Forge
Price was $1,227, price is now $852 per person
$852
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Knoxville (TYS)
8.4/10 Very Good! (1,224 reviews)
Very nice stay. Breakfast was great!

Reviewed on Aug 19, 2025

Marriott Knoxville Downtown

Marriott Knoxville Downtown

4 out of 5
Downtown Knoxville
Save 100% on your flight
Price was $1,032, price is now $724 per person
$724
per person
Nov 3 - Nov 7
found 1 day ago
Roundtrip flight included
Houston (HOU) to Knoxville (TYS)
9/10 Wonderful! (559 reviews)
Much traffic noise.

Reviewed on Aug 17, 2025

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Discover the most popular places to visit in Middlesboro

Middlesboro Mall

4/5(13 reviews)

You can search for that perfect souvenir at Middlesboro Mall during your visit to Middlesboro. Discover the mountain views while you're in the area.

Middlesboro Mall

Middlesboro Country Club

Enjoy a round of golf in Middlesboro at Middlesboro Country Club. Discover the mountain views while you're in the area.

Middlesboro Country Club

Bell County Historical Society Museum

4/5(2 reviews)

You can spend an afternoon exploring the galleries in Bell County Historical Society Museum during your travels in Middlesboro. Discover the mountain views while you're in the area.

Bell County Historical Society Museum

Middlesboro Hotel Deals

Sleep Inn & Suites

Sleep Inn & Suites

2.5 out of 5
1260 N, 12th Street, Middlesboro, KY
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $103 total per night from Sep 7 to Sep 8
$103 total
Sep 7 - Sep 8
Total with taxes and fees
9/10 Wonderful! (764 reviews)
"The elevator was out the entire duration of our stay. It had been out the previous week as well."

Reviewed on Aug 21, 2025

Sleep Inn & Suites
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
$111 nightly
The price is $122 total per night from Aug 31 to Sep 1
$122 total
Aug 31 - Sep 1
Total with taxes and fees
9.4/10 Exceptional! (672 reviews)
"The lady that checked me in and checked me out was excellent"

Reviewed on Aug 18, 2025

Holiday Inn Express Middlesboro by IHG
Econo Lodge Middlesboro

Econo Lodge Middlesboro

2 out of 5
1623 Cumberland Avenue, Middlesboro, KY
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $93 total per night from Aug 24 to Aug 25
$93 total
Aug 24 - Aug 25
Total with taxes and fees
7.2/10 Good! (426 reviews)
"Friendly efficient check in. The rooms were impressively clean and neat. The pool was clean and well cared for."

Reviewed on Aug 18, 2025

Econo Lodge Middlesboro
See all 325 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.

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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 $321 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.