Deals on vacations and trips to Middlesboro
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Middlesboro flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Westgate Smoky Mountain Resort & Water Park
Save 100% on your flight
per person
Sep 25 - Sep 28
found 13 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Knoxville (TYS)
A full-service spa, 3 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Enjoy the 2 hot tubs and perks like free WiFi. You'll appreciate the gym, bar/lounge, and laundry facilities.
Sunrise Ridge Resort
Save 100% on your flight
per person
Aug 28 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Knoxville (TYS)
2 hot tubs, an indoor pool, and a gym are all featured at this smoke-free resort. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi.
The Oliver Hotel
Downtown Knoxville
Save 100% on your flight
per person
Aug 14 - Aug 18
found 15 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Knoxville (TYS)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A snack bar/deli, express check-in, and a computer station are also on offer.
Country Cascades Waterpark Resort
Downtown Pigeon Forge
Save 100% on your flight
per person
Aug 28 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Knoxville (TYS)
Free water park access, 2 restaurants, and an indoor pool are all featured at this traditional hotel. There's fun for all ages with a free kid's club and a bowling alley, and families will appreciate the onsite laundry facilities. Enjoy a meal in one of the 2 coffee shops/cafes and free perks like free self parking and WiFi in public areas.
Courtyard by Marriott Gatlinburg Downtown
per person
Sep 25 - Sep 28
found 13 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Knoxville (TYS)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
Top Middlesboro hotels deals
Econo Lodge Middlesboro
1623 Cumberland Avenue, Middlesboro, KY
Free Cancellation
Reserve now, pay when you stay
$86 nightly
The price is $94 total per night
$94 total
Jul 20 - Jul 21
Total includes taxes and fees
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
Sleep Inn & Suites
1260 N, 12th Street, Middlesboro, KY
Free Cancellation
Reserve now, pay when you stay
$107 nightly
The price is $118 total per night
$118 total
Jul 27 - Jul 28
Total includes taxes and fees
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
Holiday Inn Express Middlesboro by IHG
1252 N 12th St, Middlesboro, KY
$123 nightly
The price is $136 total per night
$136 total
Jul 27 - Jul 28
Total includes taxes and fees
This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Holiday Inn Express Williamsburg by IHG
56 West Highway 92, Williamsburg, KY
Free Cancellation
$101 nightly
The price is $112 total per night
$112 total
Jul 20 - Jul 21
Total includes taxes and fees
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
Pine Mountain State Resort Park
1050 State Park Road, Pineville, KY
Free Cancellation
Reserve now, pay when you stay
$142 nightly
The price is $157 total per night
$157 total
Jul 24 - Jul 25
Total includes taxes and fees
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
Days Inn by Wyndham Jellico - Tennessee State Line
1417 5th Street, Jellico, TN
Free Cancellation
Reserve now, pay when you stay
$66 nightly
The price is $75 total per night
$75 total
Jul 20 - Jul 21
Total includes taxes and fees
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 seasonal outdoor pool and free perks like on-the-go breakfast and free self parking.
Pool
Hot Tub
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
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 Country Club
Enjoy a round of golf in Middlesboro at Middlesboro Country Club. Discover the mountain views while you're in the area.
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.
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