
Middlesboro Vacations from $297
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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.


Smith Creek Resort
Price was $5,164, price is now $3,443 per person
$3,443
per person
Dec 21 - Dec 24
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Knoxville (TYS)
10/10 Exceptional! (3 reviews)
⭐⭐⭐⭐⭐
Ashridge at Smith Creek Resort exceeded every expectation! If you’re looking for an upscale getaway in the Smoky Mountains, this is it.
The resort truly has everything you could want. The pool and lazy river are absolutely incredible and create the perfect place to relax, while the cabins are beautifully designed, luxurious, spacious, and equipped with everything you need to feel right at home.
One of the best parts is the location. You’re only about 6 minutes from grocery stores and everyday essentials, and within 10 minutes of restaurants, dinner shows, shopping, Dollywood, and plenty of places to pick up souvenirs. Even downtown Gatlinburg is only about a 23-minute drive away, making it easy to enjoy everything the Smoky Mountains have to offer without staying in the middle of the crowds.
What impressed me most was how versatile this resort is. During our stay, we saw family reunions, bachelorette parties, church groups, couples, and families with children all enjoying themselves. There truly is something for everyone.
Whether you’re planning a weekend escape, a family vacation, or a large group gathering, Ashridge at Smith Creek Resort is the perfect destination. We absolutely loved our stay and can’t wait to come back!
Reviewed on Jul 1, 2026

Smokies Sanctuary
Price was $736, price is now $501 per person
$501
per person
Feb 4 - Feb 7
found 1 day ago
Roundtrip flight included
Miami (MIA) to Knoxville (TYS)
10/10 Exceptional! (1 review)
Beautiful place. Amazing views. I would stay here every time. The property owners were very nice and answered any questions I had. They made sure I was taken care of. If you are in pigeon forge or gatlinburg, stay here.
Reviewed on Jul 17, 2026


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Middlesboro Hotel Deals

Sleep Inn & Suites Middlesboro
1260 N, 12th Street Middlesboro KY
Fully refundable
$95 nightly
The price is $105 total per night from Dec 2 to Dec 3
$105 total
Dec 2 - Dec 3
Total with taxes and fees
9.2/10 Wonderful! (958 reviews)
"Very friendly staff"
Reviewed on Nov 8, 2026

Econo Lodge Middlesboro
1623 Cumberland Avenue Middlesboro KY
Fully refundable
$80 nightly
The price is $88 total per night from Nov 22 to Nov 23
$88 total
Nov 22 - Nov 23
Total with taxes and fees
7.4/10 Good! (511 reviews)
"Soon as we arrived, we were met by Susan who worked inside. ..so friendly ,helpful ,..such a warm welcoming and that’s the beginning of an awesome stay ..we made coffeees (delicious) and she gave us some snacks ..room was awesome and clean as a whistle ..breakfast was delicious ..just go you won’t ..."
Reviewed on Nov 4, 2026

Suburban Studios Middlesboro
1623 Cumberland Avenue Building B Middlesboro KY
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $80 total per night from Dec 5 to Dec 6
$80 total
Dec 5 - Dec 6
Total with taxes and fees
8.4/10 Very Good! (123 reviews)
"Not well insulated and neighbors & dogs very loud."
Reviewed on Nov 9, 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.
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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- Smith Recreation Area Beach
- Black Mountain Offroad Adventure Area - Putney Trailhead
- The Harlan Center
- Pine Mountain State Resort Park
- Boone's Ridge Wildlife Park
- Pine Knot Vacations
- Bell County Historical Society Museum
- Bimble Vacations
- Visit Artemus
- Corbin Vacations
- London Dragway
- Big Hickory Golf Course
- Visit Barbourville
- Kentucky Ridge State Forest
- Visit Frakes
- Visit Calvin
- Hima Vacations
- Levi Jackson Wilderness Road State Park
- Strunk Vacations
- Visit Pineville
- Wasioto Winds Golf Course
- Holly Bay Marina
- Middlesboro Mall
- University of the Cumberlands
- Cumberland Falls
- The Arena at SE KY Agricultural and Expo Complex
- Manchester Vacations
- Pineville Vacations
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- Visit Middlesboro
- Rapid River Lodge & Water Park
- Williamsburg Vacations
- Kentucky Splash Water Park
- Harlan Vacations
- Laurel River Lake
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















