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.
Staybridge Suites Knoxville-West by IHG
Knoxville West
Price was CA $1,247, price is now CA $1,125 per person
CA $1,125
per person
Mar 24 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Knoxville (TYS)
8.8/10 Excellent! (619 reviews)
Staff was polite and courteous. Southern charm from all. Property was set back away from others with very safe feeling. Great 2 night stay!
Reviewed on Jan 12, 2026
Hilton Knoxville
Downtown Knoxville
Price was CA $3,157, price is now CA $2,599 per person
CA $2,599
per person
Mar 23 - Mar 29
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YTO) to Knoxville (TYS)
8.6/10 Excellent! (1,703 reviews)
Front desk staff was awesome. The air handling unit in our room was squeaky, even after a maintenance call and our keyless entry lost power. Not really anyone’s fault, just lessened the experience.
Reviewed on Feb 12, 2026
Hyatt Place Knoxville Downtown
Downtown Knoxville
Price was CA $3,429, price is now CA $2,902 per person
CA $2,902
per person
Mar 23 - Mar 29
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YTO) to Knoxville (TYS)
9.4/10 Exceptional! (1,002 reviews)
The room was very clean. Plus the snow they took care of us even in the cold. Made sure that we had food,heat and anything that we needed.
Reviewed on Feb 7, 2026
Comfort Suites Knoxville East
Strawberry Plains Pike
Price was CA $1,489, price is now CA $1,268 per person
CA $1,268
per person
Mar 24 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Knoxville (TYS)
8.4/10 Very Good! (1,001 reviews)
It was a good hotel for the east side of Knoxville since I had to head east the next day so I would drive against rush hour traffic.
Reviewed on Feb 4, 2026
Hampton Inn Oak Ridge Knoxville
Price was CA $1,567, price is now CA $1,360 per person
CA $1,360
per person
Mar 24 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Knoxville (TYS)
8.8/10 Excellent! (542 reviews)
Front desk area was under renovation, even during breakfast. Early morning traffic on Illinois Street woke us up. Not relaxing and restful as I would have expected from Hampton Inn.
Reviewed on Nov 6, 2025
Middlesboro Hotel Deals
Sleep Inn & Suites Middlesboro
1260 N, 12th Street Middlesboro KY
Fully refundable
The price is CA $134 per night from Feb 22 to Feb 23
CA $134
CA $151 total
Feb 22 - Feb 23
includes taxes & fees
9/10 Wonderful! (820 reviews)
Belinda at the desk is amazing She made our stay excellent , she made us feel like we were old friends . We will be staying here on each visit .
Reviewed on Jan 24, 2026
Boone Trail Inn
2105 US HIGHWAY 25 E Middlesboro KY
Fully refundableReserve now, pay when you stay
The price is CA $82 per night from Feb 15 to Feb 16
CA $82
CA $113 total
Feb 15 - Feb 16
includes taxes & fees
7.2/10 Good! (108 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
Holiday Inn Express Williamsburg by IHG
56 West Highway 92 Williamsburg KY
Fully refundable
The price is CA $163 per night from Feb 25 to Feb 26
CA $163
CA $184 total
Feb 25 - Feb 26
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
Pleasant front desk staff. Room was clean spacious room with comfortable bedding. Continental breakfast was decent and always comes in handy! Located close to Walmart and fast food restaurants for quick shopping and dining.
Reviewed on Feb 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.
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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.
