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
Price was CA $2,986, price is now CA $1,970 per person
CA $1,970
per person
Mar 16 - Mar 23
found 4 hours ago
Roundtrip flight included
Calgary (YYC) to Knoxville (TYS)
9.8/10 Exceptional! (649 reviews)
Check in was easy, the staff was amazing. Love the library. The hotel exceeded all expectations. Had a old/classic feel, yet was well taken care of, clean, with modern amenities.
Reviewed on Feb 3, 2026
Cumberland House Knoxville, Tapestry Collection by Hilton
Downtown Knoxville
Price was CA $2,176, price is now CA $1,714 per person
CA $1,714
per person
Mar 16 - Mar 23
found 4 hours ago
Roundtrip flight included
Calgary (YYC) to Knoxville (TYS)
9.2/10 Wonderful! (1,005 reviews)
It’s a very convenient location however a few issues we had:
1. One elevator was down most of the time we were there.
2. Our 3 key cards were all disabled the second day
3. Television stopped working the last night and the morning we checked out.
4. Valet parking is very expensive. Parked and didn’t use the car for 3 days and it cost $120. That’s a lot for hotel parking.
Staff was friendly and location was great.
Reviewed on Feb 1, 2026
Hyatt Place Knoxville Downtown
Downtown Knoxville
Price was CA $2,259, price is now CA $1,826 per person
CA $1,826
per person
Mar 16 - Mar 23
found 4 hours ago
Roundtrip flight included
Calgary (YYC) to Knoxville (TYS)
9.4/10 Exceptional! (1,002 reviews)
Nice entrance. Good breakfast. Friendly staff.
Reviewed on Feb 2, 2026
Middlesboro Hotel Deals
Sleep Inn & Suites Middlesboro
1260 N, 12th Street Middlesboro KY
Fully refundable
The price is CA $128 per night from Feb 26 to Feb 27
CA $128
CA $144 total
Feb 26 - Feb 27
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
Holiday Inn Express Middlesboro by IHG
1252 N 12th St Middlesboro KY
Fully refundable
The price is CA $166 per night from Feb 15 to Feb 16
CA $166
CA $183 total
Feb 15 - Feb 16
includes taxes & fees
9.4/10 Exceptional! (701 reviews)
Clean room
Reviewed on Jan 14, 2026
Boone Trail Inn
2105 US HIGHWAY 25 E Middlesboro KY
Fully refundableReserve now, pay when you stay
The price is CA $83 per night from Mar 6 to Mar 7
CA $83
CA $114 total
Mar 6 - Mar 7
includes taxes & fees
7.2/10 Good! (107 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
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.
