Middlesboro Vacations from $399

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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.
Super 8 by Wyndham Knoxville Downtown Area

Super 8 by Wyndham Knoxville Downtown Area

2 out of 5
Inskip
Price was $1,092, price is now $399 per person
$399
per person
Jan 6 - Jan 9
found 5 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Knoxville (TYS)
6.2/10 (1,004 reviews)
This motel is an excellent budget option. It is a relatively modern building with clean rooms and amenities that work well. Parking is easy and Uber pick ups and drop offs are also easy. It is surrounded by fast food options and other businesses like a laundry and petrol station.

Reviewed on Oct 24, 2025

Americas Best Value Inn - Knoxville East

Americas Best Value Inn - Knoxville East

2.5 out of 5
Strawberry Plains Pike
Price was $1,114, price is now $423 per person
$423
per person
Jan 6 - Jan 9
found 5 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Knoxville (TYS)
8.2/10 Very Good! (884 reviews)
A nice, clean economical place to stay

Reviewed on Oct 21, 2025

La Quinta Inn & Suites by Wyndham Knoxville East

La Quinta Inn & Suites by Wyndham Knoxville East

3 out of 5
Strawberry Plains Pike
Price was $1,158, price is now $443 per person
$443
per person
Jan 6 - Jan 9
found 5 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Knoxville (TYS)
7.8/10 Good! (1,005 reviews)
Breakfast was a bust.

Reviewed on Oct 26, 2025

Comfort Suites Knoxville East

Comfort Suites Knoxville East

2.5 out of 5
Strawberry Plains Pike
Price was $1,152, price is now $460 per person
$460
per person
Jan 6 - Jan 9
found 5 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Knoxville (TYS)
8.4/10 Very Good! (985 reviews)
Courteous staff. Clean room. Conveniently located.

Reviewed on Oct 29, 2025

Holiday Inn Express & Suites Oak Ridge by IHG

Holiday Inn Express & Suites Oak Ridge by IHG

2.5 out of 5
Price was $1,212, price is now $496 per person
$496
per person
Jan 6 - Jan 9
found 8 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Knoxville (TYS)
9.2/10 Wonderful! (545 reviews)
My stay is always great. However the rooms and a little dirty especially in the bathroom With hair and stuff all in the tub other than that. It’s always great. Ty.

Reviewed on Oct 23, 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

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
$120 nightly
The price is $132 total per night from Nov 16 to Nov 17
$132 total
Nov 16 - Nov 17
Total with taxes and fees
9.4/10 Exceptional! (682 reviews)
Great breakfast. Room was spacious, clean and the dove products in the bathroom were nice. Great stay.

Reviewed on Oct 19, 2025

Holiday Inn Express Middlesboro by IHG
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 Nov 16 to Nov 17
$103 total
Nov 16 - Nov 17
Total with taxes and fees
9/10 Wonderful! (797 reviews)
Clean, super nice staff, bed comfortable

Reviewed on Oct 23, 2025

Sleep Inn & Suites
Econo Lodge Middlesboro

Econo Lodge Middlesboro

2 out of 5
1623 Cumberland Avenue, Middlesboro, KY
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $88 total per night from Nov 23 to Nov 24
$88 total
Nov 23 - Nov 24
Total with taxes and fees
7.2/10 Good! (441 reviews)
Clean rooms

Reviewed on Oct 26, 2025

Econo Lodge Middlesboro
See all 341 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 $399 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.