Middlesboro Vacations from $479
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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.
The Latest Middlesboro vacation packages
Price found within the past 48 hours. Click for updated prices.
Westgate Smoky Mountain Resort & Water Park
Save 100% on your flight
Price was $898, price is now $510 per person
$510
per person
Feb 11 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Knoxville (TYS)
16.8/10 Exceptional! (1,122 reviews)
Best Location, new units, Indoor water park
Reviewed on Nov 5, 2025
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See all available trips from Columbus to Middlesboro
View all tripsDiscover the most popular places to visit in Middlesboro
Middlesboro Mall
4/5(13 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.
Bell County Historical Society Museum
4/5(2 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.
Middlesboro Country Club
Enjoy a round of golf in Middlesboro at Middlesboro Country Club. Discover the mountain views while you're in the area.
Middlesboro Hotel Deals
Sleep Inn & Suites Middlesboro
1260 N, 12th Street Middlesboro KY
Fully refundable
$94 nightly
The price is $103 total per night from Dec 14 to Dec 15
$103 total
Dec 14 - Dec 15
Total with taxes and fees
9/10 Wonderful! (802 reviews)
The breakfast was very fresh with good flavor.
Reviewed on Nov 11, 2025
Econo Lodge Middlesboro
1623 Cumberland Avenue Middlesboro KY
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $83 total per night from Nov 20 to Nov 21
$83 total
Nov 20 - Nov 21
Total with taxes and fees
7.2/10 Good! (441 reviews)
Clean rooms
Reviewed on Oct 26, 2025
Holiday Inn Express Middlesboro by IHG
1252 N 12th St Middlesboro KY
Fully refundable
$118 nightly
The price is $130 total per night from Nov 23 to Nov 24
$130 total
Nov 23 - Nov 24
Total with taxes and fees
9.4/10 Exceptional! (690 reviews)
Very comfortable and clean.
Reviewed on Nov 7, 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.
Find the Best Middlesboro Vacation Packages
Middlesboro Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 10,700 |
Max Temp Winter | 45ºF |
Max Temp Summer | 85ºF |
Top Sights | Pine Mountain State Resort Park, Bell County Historical Society Museum and Middlesboro Mall |
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- Hotels near Middlesboro Mall
- Hotels near The Pinnacle
- Hotels near Wasioto Winds Golf Course
- Hotels near Pine Mountain State Resort Park
- Calvin Hotels
- Motels in Calvin
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- Pineville Hotels
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- Bell County Historical Society Museum
- Middlesboro Mall
- Wasioto Winds Golf Course
- Pine Mountain State Resort Park
- Visit Calvin
- Visit Pineville
- Visit Frakes
- Visit Artemus
- Visit Bryants Store
- Bimble Vacations
- Dr Thomas Walker State Park
- Visit Bimble
- Visit Barbourville
- Visit Stoney Fork
- Visit Heidrick
- Visit Coldiron
- Wallins Creek Vacations
- Visit Wallins Creek
- Visit Girdler
- Williamsburg Vacations
- University of the Cumberlands
- Visit Grays Knob
- Visit Loyall
- Visit Williamsburg
- Car rentals near Calvin
- Car rentals near Laurel Lakes
- Car rentals near Pineville
- Car rentals near Frakes
- Car rentals near Artemus
- Car rentals near Bryants Store
- Car rentals near Bimble
- Car rentals near Barbourville
- Hertz Rental Cars in Barbourville
- Car rentals near Heidrick
- Car rentals near Saxton
- Car rentals near Pleasant View
- Car rentals near Grays Knob
- Car rentals near Loyall
- Car rentals near Williamsburg
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
