Middlesboro Vacations from $558

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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.
Westgate Smoky Mountain Resort & Water Park

Westgate Smoky Mountain Resort & Water Park

4 out of 5
Price was $787, price is now $558 per person
$558
per person
Oct 1 - Oct 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Knoxville (TYS)
8.4/10 Very Good! (1,257 reviews)
When having this listing on Expedia, it should clearly say that waterpark is not included with the resort. It’s very misleading. So you make reservations because you want to take your kids to a waterpark and turn around and have to spend additional money for waterpark tickets.

Reviewed on Jul 6, 2026

The Ramsey Hotel and Convention Center Pigeon Forge

The Ramsey Hotel and Convention Center Pigeon Forge

3 out of 5
Downtown Pigeon Forge
Price was $1,236, price is now $866 per person
$866
per person
Sep 20 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Knoxville (TYS)
8.4/10 Very Good! (1,550 reviews)
It was a very nice hotel. The beds were comfortable and the rooms were clean. The indoor pool and hot tub were also very nice and clean. The all you can eat breakfast buffet was very good.

Reviewed on Jul 7, 2026

Moondance Cabin by Lightfoot Stays

Moondance Cabin by Lightfoot Stays

5 out of 5
Wears Valley
Price was $1,006, price is now $729 per person
$729
per person
Sep 9 - Sep 13
found 19 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Knoxville (TYS)
10/10 Exceptional! (8 reviews)
Great experience all the way around. Would recommend, and would stay again. Everything in the description was very accurate.

Reviewed on Jun 17, 2026

Laurel Point Resort

Laurel Point Resort

2.5 out of 5
Chalet Village
Price was $806, price is now $584 per person
$584
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Knoxville (TYS)
9/10 Wonderful! (328 reviews)
This was a great place, up in the mountains, within the Smokey National Park. The last turn in and up to the property was sharp and somewhat tricky to see from the one direction, so just know that. I for one wanted to see bears and the fam and I saw 3 - it was great! Our room(s) were much larger than expected and my son really enjoyed the jet bath!

Reviewed on Jul 4, 2026

Holiday Inn Express Gatlinburg Downtown by IHG

Holiday Inn Express Gatlinburg Downtown by IHG

2.5 out of 5
Price was $905, price is now $657 per person
$657
per person
Sep 26 - Oct 1
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Knoxville (TYS)
9.2/10 Wonderful! (1,007 reviews)
Super convenient location to downtown Gatlinburg with plenty of places that are walkable.

Reviewed on Jul 7, 2026

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Stay 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.
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Middlesboro Hotel Deals

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

2.5 out of 5
1260 N, 12th Street Middlesboro KY
Fully refundable
$103 nightly
The price is $114 total per night from Aug 2 to Aug 3
$114 total
Aug 2 - Aug 3
Total with taxes and fees
9.2/10 Wonderful! (898 reviews)
"Very nice"

Reviewed on Jul 2, 2026

Sleep Inn & Suites Middlesboro
Econo Lodge Middlesboro

Econo Lodge Middlesboro

2 out of 5
1623 Cumberland Avenue Middlesboro KY
Fully refundableReserve now, pay when you stay
$82 nightly
The price is $90 total per night from Aug 6 to Aug 7
$90 total
Aug 6 - Aug 7
Total with taxes and fees
7.4/10 Good! (487 reviews)
"Don’t judge a book by its cover! This little side of the road hotel was clean, the staff was amazing! And while your in town go to shades steakhouse"

Reviewed on Jul 2, 2026

Econo Lodge 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
$144 nightly
The price is $159 total per night from Aug 6 to Aug 7
$159 total
Aug 6 - Aug 7
Total with taxes and fees
9.6/10 Exceptional! (725 reviews)
"We checked in around 8pm and were greeted by the front desk staff was fantastic. They interacted with my 11-year-old great-niece in the best way. Sharing jokes and talking to her directly on her level. Of course, the adults felt comfortable and welcome as well. The pool was very nice and clean. The ..."

Reviewed on Jun 27, 2026

Holiday Inn Express Middlesboro by IHG
See all 361 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 $558 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.