Middlesboro Vacations from $586

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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 $858, price is now $586 per person
$586
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip flight included
Miami (MIA) to Knoxville (TYS)
7.8/10 Good! (1,002 reviews)
The staff makes this place great. Super kind. Very clean. Be wary of people trying to swindle you into a timeshare though. Don't ruin your vacation!!

Reviewed on Jan 12, 2026

Laurel Point Resort

Laurel Point Resort

2.5 out of 5
Chalet Village
Price was $852, price is now $599 per person
$599
per person
Mar 19 - Mar 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Knoxville (TYS)
8.8/10 Excellent! (316 reviews)
Great place with great views!! Need to make it a little more homey, like with throw blankets and pillows in living area. Also a few games to play or books.

Reviewed on Nov 14, 2025

Holiday Inn Club Vacations Smoky Mountain Resort by IHG

Holiday Inn Club Vacations Smoky Mountain Resort by IHG

3 out of 5
Save 100% on your flight
Price was $1,419, price is now $1,004 per person
$1,004
per person
Mar 26 - Apr 2
just found
Roundtrip flight included
Dallas (DFW) to Knoxville (TYS)
9/10 Wonderful! (472 reviews)
Room was clean, but no housekeeping service during our 4 night stay. Bed was comfortable and room was nice and spacious. However the construction and landscaping noise starts early and be prepared for badgering from the timeshare sales staff. Walking distance to downtown and easy parking at hotel. View from the room was very nice. Fireplace is a nice touch.

Reviewed on Nov 2, 2025

The Resort at Governor's Crossing

The Resort at Governor's Crossing

3.5 out of 5
Governor’s Crossing
Price was $852, price is now $611 per person
$611
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Knoxville (TYS)
8.8/10 Excellent! (1,719 reviews)
Clean room. Great staff. Great rate.

Reviewed on Jan 11, 2026

The Oliver Hotel

The Oliver Hotel

3.5 out of 5
Downtown Knoxville
Price was $1,091, price is now $785 per person
$785
per person
Mar 17 - Mar 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Knoxville (TYS)
9.8/10 Exceptional! (649 reviews)
Perfect stay! Quiet, charmingly decorated, comfortable, and ideally situated for fun explorations. There is not a single thing I can suggest. It was perfect in every way!

Reviewed on Jan 10, 2026

Don't see what you're looking for?
See all available trips from Columbus to Middlesboro
View all trips

Discover the most popular places to visit in Middlesboro

Middlesboro Mall

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

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 Middlesboro

Sleep Inn & Suites Middlesboro

2.5 out of 5
1260 N, 12th Street Middlesboro KY
Fully refundable
$94 nightly
The price is $103 total per night from Feb 8 to Feb 9
$103 total
Feb 8 - Feb 9
Total with taxes and fees
9/10 Wonderful! (817 reviews)
Room and all public areas very clean Breakfast was great Elevator was down but staff went above and beyond to accommodate any inconvenience including discounts arranged with local restaurants. Completely unnecessary but very appreciated. We will stay there again

Reviewed on Jan 10, 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
$114 nightly
The price is $126 total per night from Jan 18 to Jan 19
$126 total
Jan 18 - Jan 19
Total with taxes and fees
9.4/10 Exceptional! (698 reviews)
Amazing guest they made it feel like home! Wonderful staff, amazing food . Great customer service ! I Highly recommend staying here. Most likely every-time we come down to visit family we will stay there.

Reviewed on Jan 3, 2026

Holiday Inn Express Middlesboro by IHG
Boone Trail Inn

Boone Trail Inn

2 out of 5
2105 US HIGHWAY 25 E Middlesboro KY
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $84 total per night from Jan 16 to Jan 17
$84 total
Jan 16 - Jan 17
Total with taxes and fees
7/10 Good! (112 reviews)
The owners and staff were quite nice. The owner brought me a blanket without me having to ask since the temp was going to drop into the 40s. Inside,the owners have done an excellent update of the rooms.Excellent value for the money.

Reviewed on Oct 21, 2025

Boone Trail Inn
See all 359 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Middlesboro vacation package cost?
You can snap up a vacation package to this destination from $586 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

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