Book Exclusive Middlesboro Vacation Packages

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Middlesboro flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Surestay Plus By Best Western Pigeon Forge

Surestay Plus By Best Western Pigeon Forge

2.5 out of 5
Downtown Pigeon Forge
Price was CA $836, price is now CA $792 per person
CA $792
per person
Aug 16 - Aug 19
found 20 hours 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 parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Island at Pigeon Forge and Dollywood 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 20 hours 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.
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 20 hours 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.
The Lodge at Camp Margaritaville

The Lodge at Camp Margaritaville

3 out of 5
Price was CA $1,066, price is now CA $981 per person
CA $981
per person
Aug 16 - Aug 19
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Knoxville (TYS)
Book a stay at this family-friendly hotel in Pigeon Forge. Enjoy free WiFi, an outdoor pool, and 2 outdoor pickleball courts. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Dollywood and Island at Pigeon Forge are located nearby.
Econo Lodge Pigeon Forge Riverside

Econo Lodge Pigeon Forge Riverside

2.5 out of 5
Price was CA $876, price is now CA $825 per person
CA $825
per person
Aug 16 - Aug 19
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Knoxville (TYS)
Book a stay at this family-friendly hotel in Pigeon Forge. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Island at Pigeon Forge and Titanic Museum 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 $172 per night
CA $172
CA $189 total
Aug 6 - Aug 7
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 $111 per night
CA $111
CA $122 total
Aug 3 - Aug 4
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
Aug 3 - Aug 4
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 $792. 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.