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.
Westgate Smoky Mountain Resort & Water Park
Price was CA $3,974, price is now CA $2,784 per person
CA $2,784
per person
Jun 12 - Jun 19
found 14 hours ago
Roundtrip non-stop flight included
International Falls (INL) to Knoxville (TYS)
8.4/10 Very Good! (1,212 reviews)
Great report. The views are fantastic, the staff is amazing. The amenities are really nice. The drive up the mountain is kind of a pain but so worth it.
Reviewed on May 9, 2026
The Lodge at Camp Margaritaville
Price was CA $3,330, price is now CA $2,769 per person
CA $2,769
per person
Jun 12 - Jun 19
found 14 hours ago
Roundtrip non-stop flight included
International Falls (INL) to Knoxville (TYS)
9.6/10 Exceptional! (967 reviews)
Place was excellent and exceeded my expectations in every way
Reviewed on May 10, 2026
The Resort at Governor's Crossing
Governor’s Crossing
Price was CA $3,128, price is now CA $2,622 per person
CA $2,622
per person
Jun 12 - Jun 19
found 14 hours ago
Roundtrip non-stop flight included
International Falls (INL) to Knoxville (TYS)
9/10 Wonderful! (1,748 reviews)
So family friendly. Its all about the kid. This place has activities all day for the kids. Nice clean rooms.
Reviewed on May 8, 2026
Middlesboro Hotel Deals
Sleep Inn & Suites Middlesboro
1260 N, 12th Street Middlesboro KY
Fully refundable
The price is CA $139 per night from May 31 to Jun 1
CA $139
CA $156 total
May 31 - Jun 1
includes taxes & fees
9.2/10 Wonderful! (870 reviews)
Lots of options, hot fresh coffee
Reviewed on May 11, 2026
Econo Lodge Middlesboro
1623 Cumberland Avenue Middlesboro KY
Fully refundableReserve now, pay when you stay
The price is CA $103 per night from May 12 to May 13
CA $103
CA $114 total
May 12 - May 13
includes taxes & fees
7.4/10 Good! (465 reviews)
Room was classic motel but updated, clean, and comfortable. I would definitely recommend!
Reviewed on May 11, 2026
Holiday Inn Express Middlesboro by IHG
1252 N 12th St Middlesboro KY
The price is CA $187 per night from May 17 to May 18
CA $187
CA $207 total
May 17 - May 18
includes taxes & fees
9.6/10 Exceptional! (719 reviews)
Convenient location to Cumberland Gap National Park. Was a quiet hotel. Our room looked out to a section of the hillside. Restaurants within walking distance and Walmart was across the street.
Reviewed on May 5, 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.
