Deals on vacations and trips to Middlesboro

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Price found within the past 48 hours. Click for updated prices.
Gatlinburg Town Square by Exploria Resorts

Gatlinburg Town Square by Exploria Resorts

2.5 out of 5
per person
Jul 27 - Jul 31
found 5 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Knoxville (TYS)
This hotel features an indoor pool and a gym. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. There's a spa tub on site, and laundry facilities and concierge services are also offered.
Westgate Smoky Mountain Resort & Water Park

Westgate Smoky Mountain Resort & Water Park

4 out of 5
per person
Jul 27 - Jul 31
found 5 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Knoxville (TYS)
This smoke-free hotel features a full-service spa, a water park, and 3 restaurants. Bring the family and enjoy the mini golf, playground, and kid-friendly dining. Enjoy the 2 outdoor pools and perks like free WiFi.
River Edge Inn

River Edge Inn

2 out of 5
Downtown Gatlinburg
per person
Jul 27 - Jul 31
found 5 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Knoxville (TYS)
An outdoor pool, free self parking, and concierge services are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A terrace, a snack bar/deli, and a lobby fireplace are also on offer.
The Historic Gatlinburg Inn

The Historic Gatlinburg Inn

2.5 out of 5
Downtown Gatlinburg
per person
Jul 27 - Jul 31
found 5 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Knoxville (TYS)
An outdoor pool, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. A garden, a lobby fireplace, and luggage storage are also on offer.
Embassy Suites By Hilton Gatlinburg Resort

Embassy Suites By Hilton Gatlinburg Resort

3.5 out of 5
per person
Jul 27 - Jul 31
found 5 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Knoxville (TYS)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and free perks like full breakfast and free self parking. You'll appreciate the lazy river, poolside bar, and concierge services.

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 $112 per night
$112
per night
Jul 7 - Jul 8
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's a gym on site, and laundry facilities and free newspapers are also offered.
Breakfast included
Pet friendly
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 $94 per night
$94
per night
Jul 14 - Jul 15
A restaurant and a seasonal outdoor pool are featured at this motel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.
Pool
Breakfast included
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 $123 per night
$123
per night
Jun 24 - Jun 25
This hotel features an indoor pool and a 24-hour gym. There's no skimping on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. A 24-hour business center, express check-out, and luggage storage are also on offer.
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 $83 per night
$83
per night
Jun 23 - Jun 24
A full-service spa and an outdoor pool are featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. Enjoy the spa tub and free perks like on-the-go breakfast and free self parking.
Pool
Hot Tub
"Our Happy Place", Floating Home, Sleeps 10; 4 bed/1.5 bath

"Our Happy Place", Floating Home, Sleeps 10; 4 bed/1.5 bath

Get rates
This houseboat features barbecue grills.
Kitchen
Washer
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 $90 per night
$90
per night
Jun 23 - Jun 24
A golf course and an outdoor pool are featured at this smoke-free hotel. Enjoy a meal from the restaurant and perks like free self parking and free WiFi. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and concierge services.
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.

Popular places to visit

Image for Middlesboro Mall

Middlesboro Mall

4/5(13 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.

Middlesboro Mall
Image for Bell County Historical Society Museum

Bell County Historical Society Museum

4/5(2 reviews)

You can spend an afternoon exploring the galleries in Bell County Historical Society Museum during your travels in Middlesboro. Discover the mountain views while you're in the area.

Bell County Historical Society Museum
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

Photos of local treasures

Browse Middlesboro vacation photos for more inspiration

Photo by Alexis Wyrick
Photo by Alexis Wyrick

Frequently asked questions

How much are vacation packages to Middlesboro?
Your travel daydreams can come true in Middlesboro for as low as $861. Our affordable package deals include flights and hotels, so organizing your itinerary will be a cinch. The only thing you’ll need to focus on is having a good time.
How long should my Middlesboro vacation be?
Many travelers spend about 2 nights in Middlesboro, but how long you stay is ultimately up to you. If you’re eager to venture out and explore all the incredible things this destination has waiting for you, why not hang around another night or two?
Where can I get the best vacation package deals for Middlesboro?
You can snap up fantastic Middlesboro package deals with Travelocity. Choose from as many as 400 air carriers and 1,000,000 properties worldwide and turn those vacation dreams into a reality.
Why should I book my Middlesboro vacation bundle with Travelocity?
Travel is all about making cherished memories and leaving all your stresses behind — which is why we have a professional team of customer service experts available 24/7 should you need them. On top of that, our Price Match Guarantee ensures you’ll always get the best price available on our impressive range of vacation packages. So what are you waiting for? There’s no time like the present to secure the vacation of a lifetime.
Can I save on my Middlesboro car rental if I bundle it with hotels and flights?
With a Middlesboro vacation package, you can combine your hotel, flight and car bookings and save loads. If you’re eager to explore the best of this fantastic city, why not head to Dollywood? This renowned sight is 55 mi from Middlesboro. With your own set of wheels, you’ll be there in a flash.
What is the best time of year to go to Middlesboro?
Vacation in and spend more of your cash on amazing experiences, rather than your hotel. This is the least costly month to lock in a stay. Prices are at their highest in , so avoid this time if you’re on a tight budget. April, July and September are the peak season months in Middlesboro. You’ll need to book early and be willing to pay higher prices. December, January and February are the least popular months to travel.
Which airport is best for Middlesboro?
That would be McGhee Tyson Airport (TYS), roughly 60 mi south of inner Middlesboro.
What is there to do in Middlesboro?
While hopping off the tourist trail is rewarding, you shouldn’t ignore the big-name attractions that make a place famous. Middlesboro Mall and Bell County Historical Society Museum are a couple of them in Middlesboro.
Where should I stay when visiting Middlesboro?
Many people check in to the Holiday Inn Express Middlesboro, an IHG Hotel. It’s the perfect base for your Middlesboro vacation.