Book Exclusive Middlesboro Vacation Packages

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Middlesboro flight + hotel packages

Prices and availability subject to change. Additional terms may apply.
Gatlinburg Town Square by Exploria Resorts

Gatlinburg Town Square by Exploria Resorts

2.5 out of 5
per person
Jun. 6 - Jun. 10
Roundtrip non-stop flight included
Toronto (YYZ) to Knoxville (TYS)
Stay at this eco-certified hotel in Gatlinburg. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ripley's Aquarium of the Smokies and Great Smoky Mountains National Park are located nearby. Discover genuine guest reviews for Gatlinburg Town Square by Exploria Resorts along with the latest prices and availability – book now.
Hilton Knoxville

Hilton Knoxville

3.5 out of 5
Downtown Knoxville
per person
Jun. 6 - Jun. 10
Roundtrip non-stop flight included
Toronto (YYZ) to Knoxville (TYS)
Stay at this business-friendly hotel in Knoxville. Enjoy free WiFi, an outdoor pool, and breakfast. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Neyland Stadium and Knoxville Zoo are located nearby. Discover genuine guest reviews for Hilton Knoxville, in Downtown Knoxville neighborhood, along with the latest prices and availability – book now.
Cedar Bluff Inn

Cedar Bluff Inn

2 out of 5
per person
Jun. 6 - Jun. 10
Roundtrip non-stop flight included
Toronto (YYZ) to Knoxville (TYS)
Stay at this business-friendly hotel in Knoxville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Turkey Creek Shopping Center and Dead Horse Lake Golf Course are located nearby. Discover genuine guest reviews for Cedar Bluff Inn along with the latest prices and availability – book now.

Top Middlesboro hotels deals

Sleep Inn & Suites

Sleep Inn & Suites

2.5 out of 5
1260 N, 12th Street, Middlesboro, KY
Free cancellation
Reserve now, pay when you stay
The price is CA $134 per night
CA $134
per night
May 12 - May 13
Stay at this business-friendly hotel in Middlesboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Middlesboro Mall and Bell County Historical Society Museum are located nearby. Discover genuine guest reviews for Sleep Inn & Suites along with the latest prices and availability – book now.
Econo Lodge Middlesboro

Econo Lodge Middlesboro

2 out of 5
1623 Cumberland Avenue, Middlesboro, KY
Free cancellation
Reserve now, pay when you stay
The price is CA $124 per night
CA $124
per night
Apr. 29 - Apr. 30
Stay at this motel in Middlesboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Bell County Historical Society Museum and Middlesboro Mall are located nearby. Discover genuine guest reviews for Econo Lodge Middlesboro along with the latest prices and availability – book now.
Holiday Inn Express Williamsburg, an IHG Hotel

Holiday Inn Express Williamsburg, an IHG Hotel

2.5 out of 5
56 West Highway 92, Williamsburg, KY
Free cancellation
The price is CA $161 per night
CA $161
per night
May 19 - May 20
Stay at this hotel in Williamsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attraction Kentucky Splash Water Park is located nearby. Discover genuine guest reviews for Holiday Inn Express Williamsburg, an IHG Hotel along with the latest prices and availability – book now.
Days Inn by Wyndham Jellico - Tennessee State Line

Days Inn by Wyndham Jellico - Tennessee State Line

2 out of 5
1417 5th Street, Jellico, TN
Free cancellation
Reserve now, pay when you stay
The price is CA $96 per night
CA $96
per night
May 6 - May 7
Stay at this spa hotel in Jellico. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Memorial Park and Indian Mountain State Park are located nearby. Discover genuine guest reviews for Days Inn by Wyndham Jellico - Tennessee State Line along with the latest prices and availability – book now.
Pine Mountain State Resort Park

Pine Mountain State Resort Park

3 out of 5
1050 State Park Road, Pineville, KY
Free cancellation
Reserve now, pay when you stay
The price is CA $164 per night
CA $164
per night
Apr. 28 - Apr. 29
Stay at this 3-star golf hotel in Pineville. Enjoy free WiFi, free parking, and a golf course. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Pine Mountain State Resort Park and Wasioto Winds Golf Course are located nearby. Discover genuine guest reviews for Pine Mountain State Resort Park along with the latest prices and availability – book now.
Dog-friendly lakefront house with hot tub, central AC, & mountain view

Dog-friendly lakefront house with hot tub, central AC, & mountain view

Get rates
Stay at this vacation home in New Tazewell. Enjoy barbecue grills, a patio, and a TV. Popular attractions Lone Mountain Boat Dock and Straight Creek Boat Dock are located nearby. Discover genuine guest reviews for Dog-friendly lakefront house with hot tub, central AC, & mountain view along with the latest prices and availability – book now.
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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.

Popular places to visit

Image for Middlesboro Mall

Middlesboro Mall

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.

Middlesboro Mall
Image for Middlesboro ARH Hospital

Middlesboro ARH Hospital

Though Middlesboro ARH Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Middlesboro while you are here.

Middlesboro ARH Hospital
Image for Middlesboro Country Club

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 Country Club

Middlesboro Vacations

If you're vacationing in Middlesboro and you don't really know a lot about it, there's no need to stress — we have you covered!

You can find it 25 miles (40 kilometers) from Williamsburg and 30 miles (48 kilometers) away from Corbin.

11,000 locals reside in this corner of Eastern Kentucky.

Places to visit in Middlesboro

Are you looking for a way to relieve the stress of your busy life? Suck in the fresh air as you embark on an adventure through Cumberland Gap National Historical Park. Need more options? History is the ultimate teacher. Drink in the knowledge and better acquaint yourself with times past at Bell County Historical Society Museum. But that's not all. Traveling can sometimes mean getting into the same old clothes day in, day out. So, if you fancy treating yourself to a new outfit, make your way over to Middlesboro Mall.

Where do you fly into for Middlesboro?

While you're planning your Middlesboro trip, keep in mind that the closest major terminal, McGhee Tyson Airport (TYS), is approximately 60 miles (97 kilometers) south of the main streets. Book your flight, fill up your luggage and get ready for some exciting new adventures!

Frequently asked questions

How much are vacation packages to Middlesboro?
You can get an excellent flight and hotel bundle from just CA $717. With a Travelocity vacation package, a trip to Middlesboro has never looked more enticing! Save your time and money and then start packing that suitcase.
How long should my Middlesboro vacation be?
There are no rules when it comes to how long your Middlesboro vacation should be, but the majority of people decide to stay for around 2 nights. Got some flexibility with your travel dates? Extend your escape by a couple more nights. Then you’ll have ample time to discover the area’s off-the-beaten-path gems too.
Where can I get the best vacation package deals for Middlesboro?
Travelocity is where to go to score a great Middlesboro package deal. Choose from as many as 400 air carriers and 665,000 properties around the world and put together a vacation package that suits your style. With so much choice, now’s the time to book your next big adventure.
Why should I book my Middlesboro vacation package via Travelocity?
Whether you’re on the hunt for the ultimate unplugged getaway or you crave the hustle and bustle of a towering metropolis, booking everything with Travelocity saves you time, hassle and money. No need to search through hundreds of different websites for the best deal — our Price Match Guarantee ensures you’ll always get the lowest price, and our team of customer service experts are available 24/7 should you need anything at all.
Can I save money on my Middlesboro car rental if I book it with my hotel or flight?
With a Middlesboro vacation package, you can bundle your hotel, flight and car bookings and save a ton. When you’re ready to explore the best of this fabulous area, why not make a beeline for Biltmore Estate? This famous attraction is 159 kilometersfrom Middlesboro. With your own wheels, you’ll be there before you know it.
What is the best time of year to go to Middlesboro?
You’ll land the best hotel prices in and pay the most in . You can usually expect it to be less busy in , while you’ll find many more fellow travelers to meet during . It comes down to how much you’re willing to pay, the weather and how well you handle crowds.
Which airport is best for Middlesboro?
Knoxville, TN (TYS-McGhee Tyson) is 95 kilometerssouth of the heart of Middlesboro.
What is there to do in Middlesboro?
Snap up the great photo-ops at Cumberland Gap National Historical Park, one of the most well-known attractions in Middlesboro. There’s plenty more to uncover in this exciting city, so make sure you have enough time to explore some hidden gems.
Where should I stay when visiting Middlesboro?
Many travelers choose to hit the hay at the Holiday Inn Express Middlesboro. It’s sure to be a good base for your Middlesboro getaway.
Can I go on vacation to Middlesboro at this time?
Our team has the local knowledge to ensure your travel dreams come true, so before planning your trip to Middlesboro, take a look at our Covid-19 Travel Advisor. Here you’ll discover all the current info about travel restrictions, quarantine policies and a whole lot more.