Book Exclusive Middlesboro Vacation Packages

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Middlesboro flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Creekstone Inn

Creekstone Inn

2 out of 5
Price was CA $969, price is now CA $873 per person
CA $873
per person
Aug 16 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Knoxville (TYS)
Stay at this hotel in Pigeon Forge. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Dollywood and Island at Pigeon Forge are located nearby.
Club Wyndham Smoky Mountains

Club Wyndham Smoky Mountains

3 out of 5
Governor’s Crossing
Price was CA $1,806, price is now CA $1,524 per person
CA $1,524
per person
Aug 28 - Sep 4
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Knoxville (TYS)
Book a stay at this family-friendly hotel in Sevierville. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Titanic Museum and Island at Pigeon Forge are located nearby.
The Ramsey Hotel and Convention Center Pigeon Forge

The Ramsey Hotel and Convention Center Pigeon Forge

3 out of 5
Downtown Pigeon Forge
Price was CA $1,081, price is now CA $925 per person
CA $925
per person
Aug 16 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Knoxville (TYS)
Book a stay at this business-friendly hotel in Pigeon Forge. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Island at Pigeon Forge and Dollywood are located nearby.
The Oliver Hotel

The Oliver Hotel

3.5 out of 5
Downtown Knoxville
Price was CA $1,888, price is now CA $1,619 per person
CA $1,619
per person
Aug 28 - Sep 4
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Knoxville (TYS)
Book a stay at this business-friendly hotel in Knoxville. Enjoy free WiFi, free bicycles on site, and valet parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Market Square and Neyland Stadium are located nearby.
Mountain Dream & Song

Mountain Dream & Song

4 out of 5
Chalet Village
Price was CA $2,104, price is now CA $1,872 per person
CA $1,872
per person
Aug 28 - Sep 4
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Knoxville (TYS)
Stay at this vacation home in Gatlinburg. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Ripley's Aquarium of the Smokies and Anakeesta are located nearby.

Top Middlesboro hotels deals

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

2.5 out of 5
1260 N, 12th Street Middlesboro KY
Free cancellation
The price is CA $152 per night
CA $152
CA $170 total
Aug 2 - Aug 3
includes taxes & fees
Book a 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.
Breakfast included
Pet-friendly
Econo Lodge Middlesboro

Econo Lodge Middlesboro

2 out of 5
1623 Cumberland Avenue Middlesboro KY
Free cancellation
The price is CA $117 per night
CA $117
CA $129 total
Aug 2 - Aug 3
includes taxes & fees
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.
Pool
Breakfast included
Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG

2.5 out of 5
1252 N 12th St Middlesboro KY
Free cancellation
The price is CA $159 per night
CA $159
CA $175 total
Jul 23 - Jul 24
includes taxes & fees
Book a 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 Cumberland Gap National Historical Park and Middlesboro Mall are located nearby.
Pool
Breakfast included
Suburban Studios Middlesboro

Suburban Studios Middlesboro

2 out of 5
1623 Cumberland Avenue Building B Middlesboro KY
Free cancellation
Reserve now, pay when you stay
The price is CA $110 per night
CA $110
CA $121 total
Aug 4 - Aug 5
includes taxes & fees
Stay at this hotel in Middlesboro. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Bell County Historical Society Museum and Middlesboro Mall are located nearby.
Pool
Breakfast included
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 $86 per night
CA $86
CA $99 total
Jul 27 - Jul 28
includes taxes & fees
Book a 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 Veterans Park and Greenlee Park are located nearby.
Breakfast included
Spa
Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG

2.5 out of 5
56 West Highway 92 Williamsburg KY
Free cancellation
The price is CA $145 per night
CA $145
CA $162 total
Jul 23 - Jul 24
includes taxes & fees
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 attractions Briar Creek Park and Kentucky Splash Water Park are located nearby.
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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.

Stay near popular Middlesboro attractions

Middlesboro Mall

7.6/10 (62 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.
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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?
Travelocity provides package deals to Middlesboro, including flights and hotels, from an impressive CA $873. With all the extra money, you could book some popular tours or possibly even add some extra nights to your adventure.
How long should my Middlesboro vacation be?
Most people choose to spend about 2 nights in Middlesboro, but how long you stay is totally up to you. If you'd like to venture out and explore all the intriguing things this location has to offer, why not hang around another few nights?
Where can I get the best vacation package deals for Middlesboro?
No matter what you enjoy doing, Travelocity can help you snap up an unbeatable Middlesboro package deal. All you need to do is mix and match from our 400 partner airlines and 1,000,000 worldwide properties.
Why should I purchase my Middlesboro vacation package via Travelocity?
With our Price Match Guarantee, we'll match any better price you find. Add on our 24/7 support and first-rate service and your perfect vacation is closer than ever before.
Will I save money on my Middlesboro car rental if I book it with a hotel or flight?
Bundling your hotel, flight and car into a Middlesboro vacation package is the best way to land the best prices. Plus, having your own car rental gives you freedom to get to all those big-name sights you want to check out. Sitting 88 kilometers away from Middlesboro, Dollywood is one attraction that should feature on your itinerary. Load up the car and make a day trip of it.
Which airport is best for Middlesboro?
McGhee Tyson Airport (TYS) sits 97 kilometers south of central Middlesboro.
Where should I stay when visiting Middlesboro?
Many visitors stay at the Holiday Inn Express Middlesboro, an IHG Hotel. It's sure to be a great base for your Middlesboro vacation.

Photos of local treasures

Browse Middlesboro vacation photos for more inspiration

An aerial view of a town surrounded by mountains, with a mix of residential and commercial buildings, and a highway running through the center.
A mountainous landscape with a town nestled in the valley.
A mountainous landscape with a town nestled in the valley, surrounded by dense forests and a winding road.
Stonehenge with standing stones and a large horizontal lintel.
A forest path surrounded by dense green ferns and trees.