Middlesboro Vacation Packages
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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.
Top Middlesboro Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Mountain Meadows
CA $1,293
per person
Sep 22 - Sep 29
found 8 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Knoxville (TYS)
8.4/10 Very good! (13 reviews)
Great distance to various things. Staff were kind and helpful. Place was perfect for our group of 5 (3 adults 2 kids) they had a pool table and ping pong table the kids enjoyed using. Will definitely stay here again!
Reviewed on Aug 9, 2026
The Lodge at Camp Margaritaville
CA $1,433
per person
Sep 22 - Sep 29
found 6 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Knoxville (TYS)
9.4/10 Exceptional! (1,007 reviews)
Absolutely loved my stay at Camp Margaritaville. The amenities are amazing, the staff was exceptional, and the rooms were BIG. I would absolutely stay here again and recommend it to everyone I know who plans a visit to Pigeon Forge, TN.
Reviewed on Aug 14, 2026
Margaritaville Island Hotel
Downtown Pigeon Forge
CA $1,922
per person
Sep 22 - Sep 29
found 8 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Knoxville (TYS)
9.4/10 Exceptional! (1,426 reviews)
Overall good stay. I’m not a fan of hotels ditching the physical soap bars though. That and the thermostat stops at 68, not so good during summer. And it seems special requests here don’t get factored into planning until the moment you check in. So if you want a room close to the elevators because walking the half mile to the other end with a blown out knee hurts, better plan for that walk. Otherwise it’s Margaritaville, what’s not to love!
Reviewed on Aug 14, 2026
Ready to book your vacation to Middlesboro?
Middlesboro Hotel Deals
Sleep Inn & Suites Middlesboro
1260 N, 12th Street Middlesboro KY
Fully refundable
CA $137
CA $154 total
Sep 10 - Sep 11
includes taxes & fees
Holiday Inn Express Middlesboro by IHG
1252 N 12th St Middlesboro KY
Fully refundable
CA $182
CA $201 total
Aug 16 - Aug 17
includes taxes & fees
9.6/10 Exceptional! (736 reviews)
"The gym is janky and almost scary. It’s very dark and just very isolated. Scary as a female to go to alone. Otherwise nice property. Gym is important to me so I would not stay here again. But I would not discourage someone who isn’t concerned about a gym to stay."
Reviewed on Aug 13, 2026
Econo Lodge Middlesboro
1623 Cumberland Avenue Middlesboro KY
Fully refundable
CA $124
CA $136 total
Aug 23 - Aug 24
includes taxes & fees
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.
Stay near popular Middlesboro attractions
Middlesboro Mall
7.6/10 (62 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 Country Club
Enjoy a round of golf in Middlesboro at Middlesboro Country Club. Discover the mountain views while you're in the area.
Bell County Historical Society Museum
8.2/10 (13 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.
Frequently asked questions
How much does a Middlesboro vacation package cost?
You'll find cheap prices from CA $1,293 on Expedia for your Middlesboro getaway. However, factors like the hotel choice, length of stay and season will influence how much your vacation to Middlesboro costs.
What are the cheapest months to go to Middlesboro?
You can usually find reduced prices and better availability in January, February and November. Check out our cheap Middlesboro vacation packages and you could score some excellent off-season deals.
How many days is enough for Middlesboro?
With a well-planned schedule, you can easily visit the main Middlesboro sights in a handful of days. But if you'd like to discover lesser-known spots or take day trips, think about booking your Middlesboro vacation for longer.
How to find the best Middlesboro package deals?
Start your search for a Middlesboro package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Middlesboro package deal right away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Middlesboro adventure off to a flying start.
Is it cheaper to book a Middlesboro vacation as a package?
You can enjoy significant savings on your next Middlesboro break by booking a personalized vacation package. Check the "Package" heading, then select your travel dates and destination to browse some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Middlesboro?
Enjoy incredible discounts by reserving your flights early with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Middlesboro break.
How to plan a trip to Middlesboro?
- Choose your dates: The things you want to do in Middlesboro and your favourite season will help you decide when to go.
- Set a budget: Factor in expenses like flights, transportation and food when working out how much to set aside for your trip to Middlesboro. Then, select a hotel that works with your budget, whether that's a wallet-friendly option or a more upscale retreat.
- Decide how many days away: Start by compiling a list of the sights and activities you'd like to experience in Middlesboro. Then, estimate how long you'll need at each, as well as any travel time.
- Bundle your airfare and accommodations: After you've nailed down your dates and duration, book the ideal Middlesboro vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
