Middlesboro Vacations from $528

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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.
The Oliver Hotel

The Oliver Hotel

3.5 out of 5
Downtown Knoxville
Price was $751, price is now $528 per person
$528
per person
Dec 12 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Knoxville (TYS)
9.6/10 Exceptional! (600 reviews)
Absolutely gorgeous and such kind staff.

Reviewed on Sep 18, 2025

Westgate Smoky Mountain Resort & Water Park

Westgate Smoky Mountain Resort & Water Park

4 out of 5
Save 100% on your flight
Price was $1,803, price is now $1,043 per person
$1,043
per person
Oct 27 - Nov 3
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Knoxville (TYS)
8.4/10 Very Good! (1,107 reviews)
Everything is great. Staff is super friendly and helpful. Only had a couple small issues, but we will definitely be staying here anytime we come back in the future.

Reviewed on Sep 17, 2025

The Ramsey Hotel & Convention Center

The Ramsey Hotel & Convention Center

3 out of 5
Downtown Pigeon Forge
Price was $1,264, price is now $887 per person
$887
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Knoxville (TYS)
8.4/10 Very Good! (1,239 reviews)
We love the lobby very nice and large sitting room fireplace large chairs and couch to relax on coffee and flavored water all day will stay again The only thing I didn't like was the lighting in the bathroom

Reviewed on Sep 19, 2025

THE TENNESSEAN Hotel

THE TENNESSEAN Hotel

4 out of 5
Downtown Knoxville
Save 100% on your flight
Price was $871, price is now $625 per person
$625
per person
Dec 12 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Knoxville (TYS)
9.4/10 Exceptional! (1,002 reviews)
Stayed here before and it’s still a great spot in Knoxville

Reviewed on Sep 19, 2025

Sunrise Ridge Resort

Sunrise Ridge Resort

3 out of 5
Price was $1,036, price is now $754 per person
$754
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Knoxville (TYS)
9/10 Wonderful! (1,006 reviews)
Very clean outside and inside,I love the amenities around the property as well

Reviewed on Sep 15, 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
$93 nightly
The price is $102 total per night from Oct 9 to Oct 10
$102 total
Oct 9 - Oct 10
Total with taxes and fees
9/10 Wonderful! (773 reviews)
"Staff were terrific. We rode motorcycles and it was pouring rain. They gave us each garbage bags to cover our bags. The elevator was down and I know they were getting some complaints but they were still very helpful and pleasant."

Reviewed on Sep 4, 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
$127 nightly
The price is $140 total per night from Sep 21 to Sep 22
$140 total
Sep 21 - Sep 22
Total with taxes and fees
9.4/10 Exceptional! (676 reviews)
"Very clean and loved that Dove products were supplied"

Reviewed on Aug 31, 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 Sep 21 to Sep 22
$93 total
Sep 21 - Sep 22
Total with taxes and fees
7.2/10 Good! (431 reviews)
"Great"

Reviewed on Sep 12, 2025

Econo Lodge Middlesboro
See all 335 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 $528 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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