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.
Country Cascades Waterpark Resort
Downtown Pigeon Forge
Save 100% on your flight
Price was $696, price is now $463 per person
$463
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) 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.
Harrah's Cherokee – A Caesars Rewards Destination
Save 100% on your flight
Price was $1,157, price is now $698 per person
$698
per person
Jan 29 - Feb 2
found 15 hours ago
Roundtrip flight included
Miami (MIA) to Knoxville (TYS)
This hotel features a casino, a full-service spa, and a nightclub. Traveling on business? Take advantage of the 24-hour business center, conference center, and conference space. Free self parking is free for guests, and you can enjoy a meal in one of the 10 restaurants.
Westgate Smoky Mountain Resort & Water Park
Price was $977, price is now $606 per person
$606
per person
Feb 13 - Feb 16
just found
Roundtrip flight included
Dallas (DFW) 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.
The Oliver Hotel
Downtown Knoxville
Save 100% on your flight
Price was $998, price is now $641 per person
$641
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) 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.
THE TENNESSEAN Hotel
Downtown Knoxville
Save 100% on your flight
Price was $909, price is now $594 per person
$594
per person
Jan 22 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Knoxville (TYS)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A snack bar/deli, a computer station, and luggage storage are also on offer.
Top Middlesboro hotels deals
Sleep Inn & Suites Middlesboro
1260 N, 12th Street Middlesboro KY
Free Cancellation
$94 nightly
The price is $103 total per night
$103 total
Dec 14 - Dec 15
Total with 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
Econo Lodge Middlesboro
1623 Cumberland Avenue Middlesboro KY
Free Cancellation
Reserve now, pay when you stay
$75 nightly
The price is $83 total per night
$83 total
Nov 23 - Nov 24
Total with 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
Holiday Inn Express Middlesboro by IHG
1252 N 12th St Middlesboro KY
Free Cancellation
$112 nightly
The price is $123 total per night
$123 total
Dec 21 - Dec 22
Total with 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
Boone Trail Inn
2105 US HIGHWAY 25 E Middlesboro KY
Free Cancellation
Reserve now, pay when you stay
$78 nightly
The price is $87 total per night
$87 total
Nov 26 - Nov 27
Total with taxes and fees
A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. Staff at the 24-hour front desk can provide around-the-clock assistance.
Pool
Pet friendly
Pine Mountain State Resort Park
1050 State Park Road Pineville KY
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $120 total per night
$120 total
Dec 18 - Dec 19
Total with 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
Holiday Inn Express Williamsburg by IHG
56 West Highway 92 Williamsburg KY
Free Cancellation
$109 nightly
The price is $121 total per night
$121 total
Nov 23 - Nov 24
Total with 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
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
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 ARH Hospital
Though Middlesboro ARH Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Middlesboro while you are here.
Bell County Historical Society Museum
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.
Frequently asked questions
Photos of local treasures
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