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.
The Oliver Hotel
Downtown Knoxville
CA $1,016
per person
Nov 8 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Knoxville (TYS)
9.8/10 Exceptional! (856 reviews)
The Oliver is a classic boutique hotel offering an exceptional level of service and quality. The location for downtown Knoxville can't be beat. It's adjacent to market square where are there so many different activities, restaurants, and shops.
Reviewed on Sep 11, 2026
THE TENNESSEAN Hotel
Downtown Knoxville
CA $4,525
per person
Oct 14 - Oct 18
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Knoxville (TYS)
9.4/10 Exceptional! (1,000 reviews)
Delightful staff, clean and bright rooms, spacious bathroom with water closet. Lovely experience.
Reviewed on Sep 12, 2026
Hilton Knoxville
Downtown Knoxville
CA $1,036
per person
Nov 8 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Knoxville (TYS)
8.6/10 Excellent! (2,134 reviews)
Room needed a bit of TLC. However, overall a great stay, very walkable area. Staff was always very pleasant to work with. Would stay here again!
Reviewed on Sep 13, 2026
Hampton Inn & Suites Knoxville-Downtown
Downtown Knoxville
CA $3,118
per person
Oct 14 - Oct 18
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Knoxville (TYS)
8.8/10 Excellent! (1,003 reviews)
Great location in beautiful Knoxville. I would either request a room not facing the road and church or make use of the provided ear plugs and sound machine. Traffic noise from the road was rather loud without the ear plugs.
Reviewed on Sep 8, 2026
Ready to book your vacation to Middlesboro?
Middlesboro Hotel Deals
Sleep Inn & Suites Middlesboro
1260 N, 12th Street Middlesboro KY
Fully refundable
CA $149
CA $167 total
Sep 27 - Sep 28
includes taxes & fees
9.2/10 Wonderful! (932 reviews)
"The male clerk"
Reviewed on Sep 12, 2026
Holiday Inn Express Middlesboro by IHG
1252 N 12th St Middlesboro KY
CA $193
CA $213 total
Sep 27 - Sep 28
includes taxes & fees
Suburban Studios Middlesboro
1623 Cumberland Avenue Building B Middlesboro KY
Fully refundableReserve now, pay when you stay
CA $109
CA $120 total
Oct 4 - Oct 5
includes taxes & fees
8.2/10 Very good! (104 reviews)
"The Good: Clean room, comfortable bedding, full size refrigerator, cook top, nice linens, plenty of parking; friendly staff; convenient to groceries, gas, dining The Bad: (1) No coffee maker in room; (2) Dirty/smelly outside of room - buckets are placed outside each room to be used as ash trays....constant ..."
Reviewed on Sep 7, 2026
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 $1,016 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.
