Book Exclusive Middlesboro Vacation Packages

Choose one or more items to build your trip:

Middlesboro flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Best Western Plaza Inn

Best Western Plaza Inn

2.5 out of 5
Price was CA $1,121, price is now CA $1,018 per person
CA $1,018
per person
Nov 20 - Nov 23
found 5 hours ago
Roundtrip non-stop flight included
Calgary (YYC) 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 pool 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 $1,478, price is now CA $1,280 per person
CA $1,280
per person
Nov 20 - Nov 23
found 5 hours ago
Roundtrip non-stop flight included
Calgary (YYC) 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.
River Edge Inn

River Edge Inn

2 out of 5
Downtown Gatlinburg
Price was CA $1,266, price is now CA $1,110 per person
CA $1,110
per person
Nov 20 - Nov 23
found 5 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Knoxville (TYS)
Stay at this hotel in Gatlinburg. Enjoy free breakfast, free WiFi, and free parking. 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.
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 $1,386, price is now CA $1,228 per person
CA $1,228
per person
Nov 20 - Nov 23
found 5 hours ago
Roundtrip non-stop flight included
Calgary (YYC) 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 Inn On The River

The Inn On The River

3 out of 5
Price was CA $1,361, price is now CA $1,218 per person
CA $1,218
per person
Nov 20 - Nov 23
found 5 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Knoxville (TYS)
Book a stay at this family-friendly hotel in Pigeon Forge. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff 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 $140 per night
CA $140
CA $157 total
Sep 27 - Sep 28
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
Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG

2.5 out of 5
1252 N 12th St Middlesboro KY
The price is CA $163 per night
CA $163
CA $180 total
Sep 6 - Sep 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 Middlesboro Mall and Bell County Historical Society Museum 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 $108 per night
CA $108
CA $119 total
Oct 1 - Oct 2
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 $81 per night
CA $81
CA $93 total
Sep 27 - Sep 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 $152 per night
CA $152
CA $169 total
Sep 7 - Sep 8
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.
Pool
Breakfast included
Quality Inn Harlan

Quality Inn Harlan

2.5 out of 5
2608 South Highway 421 Harlan KY
Free cancellation
The price is CA $128 per night
CA $128
CA $145 total
Sep 13 - Sep 14
includes taxes & fees
Book a stay at this business-friendly hotel in Harlan. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews.
Breakfast included
Pet-friendly
Don't see what you're looking for?
See all available properties in Middlesboro
View all properties
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.
See properties

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 $1,018. 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.