Middlesboro Vacations from $396

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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

River Terrace Resort & Convention Center

3.5 out of 5
Downtown Gatlinburg
Price was $587, price is now $396 per person
$396
per person
Apr 24 - Apr 26
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Knoxville (TYS)
7.6/10 Good! (1,002 reviews)
Nice room perfect location

Reviewed on Feb 14, 2026

The Ramsey Hotel & Convention Center

The Ramsey Hotel & Convention Center

3 out of 5
Downtown Pigeon Forge
Save 100% on your flight
Price was $1,246, price is now $810 per person
$810
per person
Apr 21 - Apr 28
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Knoxville (TYS)
8.4/10 Very Good! (1,299 reviews)
Very clean and nice area

Reviewed on Mar 6, 2026

Creekstone Inn

Creekstone Inn

2 out of 5
Price was $754, price is now $528 per person
$528
per person
May 12 - May 19
found 22 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Knoxville (TYS)
9/10 Wonderful! (2,882 reviews)
Anytime we stay in pigeon forge we stay at creekside inn as it’s close to everything and during the summer time your able to have fun in the creek.

Reviewed on Mar 5, 2026

Holiday Inn Express Gatlinburg Downtown by IHG

Holiday Inn Express Gatlinburg Downtown by IHG

2.5 out of 5
Save 100% on your flight
Price was $1,172, price is now $843 per person
$843
per person
May 20 - May 24
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Knoxville (TYS)
9.2/10 Wonderful! (1,001 reviews)
Very clean, super nice hotel staff, and comfortable room. The Breakfast bar was nice, clean, plenty to eat and nice staff. This hotel is within comfortable walking distance to downtown Gatlinburg.

Reviewed on Mar 5, 2026

The Lodge at Camp Margaritaville

The Lodge at Camp Margaritaville

3 out of 5
Price was $998, price is now $722 per person
$722
per person
May 12 - May 19
found 22 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Knoxville (TYS)
9.6/10 Exceptional! (882 reviews)
Clean room, staff, pool

Reviewed on Mar 1, 2026

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Discover the most popular places to visit in Middlesboro

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 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

Middlesboro Hotel Deals

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

2.5 out of 5
1260 N, 12th Street Middlesboro KY
Fully refundable
$105 nightly
The price is $115 total per night from Mar 15 to Mar 16
$115 total
Mar 15 - Mar 16
Total with taxes and fees
9.2/10 Wonderful! (829 reviews)
The staff is attentive and helpful. The room is large and clean. Now the bad. Tv and wifi are a joke!! The TVs are so old you can’t stream on them. I constantly have to go to my truck to get proper internet access. This is extremely annoying and corporate doesn’t care from what I hear. This makes ...

Reviewed on Feb 27, 2026

Sleep Inn & Suites 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
$137 nightly
The price is $151 total per night from Mar 15 to Mar 16
$151 total
Mar 15 - Mar 16
Total with taxes and fees
9.6/10 Exceptional! (705 reviews)
Very nice and clean.

Reviewed on Feb 21, 2026

Holiday Inn Express Middlesboro by IHG
Suburban Studios Middlesboro

Suburban Studios Middlesboro

2 out of 5
1623 Cumberland Avenue Building B Middlesboro KY
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $81 total per night from Mar 22 to Mar 23
$81 total
Mar 22 - Mar 23
Total with taxes and fees
Suburban Studios Middlesboro
See all 351 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.

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 $396 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.