Book Exclusive Middlesboro Vacation Packages

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Middlesboro flight + hotel packages

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

Wild Bear Inn

3 out of 5
Price was CA $2,019, price is now CA $1,614 per person
CA $1,614
per person
Dec 30 - Jan 3
found 10 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Knoxville (TYS)
Stay at this hotel in Pigeon Forge. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Dollywood and Dolly Parton's Stampede Dinner Attraction are located nearby.
The Lodge at Camp Margaritaville

The Lodge at Camp Margaritaville

3 out of 5
Price was CA $2,059, price is now CA $1,795 per person
CA $1,795
per person
Dec 30 - Jan 3
found 10 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 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 Dolly Parton's Stampede Dinner Attraction are located nearby.
Sunrise Ridge Resort

Sunrise Ridge Resort

2 out of 5
Price was CA $1,941, price is now CA $1,696 per person
CA $1,696
per person
Dec 30 - Jan 3
found 10 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Knoxville (TYS)
Stay at this hotel in Pigeon Forge. Enjoy free WiFi, free parking, and concierge services. Popular attractions Dollywood and Dollywood's Splash Country are located nearby.
Lodge at Mill Creek

Lodge at Mill Creek

2.5 out of 5
Price was CA $1,793, price is now CA $1,639 per person
CA $1,639
per person
Dec 30 - Jan 3
found 10 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Knoxville (TYS)
Stay at this hotel in Pigeon Forge. Enjoy free WiFi, free parking, and an area shuttle (surcharge). Popular attractions Dollywood and Dolly Parton's Stampede Dinner Attraction are located nearby.
Best Western Toni Inn

Best Western Toni Inn

2.5 out of 5
Price was CA $1,874, price is now CA $1,716 per person
CA $1,716
per person
Dec 30 - Jan 3
found 10 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 Dolly Parton's Stampede Dinner Attraction 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 $167 per night
CA $167
CA $187 total
Nov 13 - Nov 14
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 $120 per night
CA $120
CA $132 total
Nov 6 - Nov 7
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
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 $105 per night
CA $105
CA $115 total
Nov 8 - Nov 9
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
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 $202 per night
CA $202
CA $223 total
Nov 19 - Nov 20
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
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 $80 per night
CA $80
CA $92 total
Oct 20 - Oct 21
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
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 $147 per night
CA $147
CA $162 total
Nov 1 - Nov 2
includes taxes & fees
Book a stay at this golf hotel in Pineville. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Pine Mountain State Resort Park and Wasioto Winds Golf Course are located nearby.
Pool
Pet-friendly
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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 Country Club

Enjoy a round of golf in Middlesboro at Middlesboro Country Club. 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 $1,614. 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.