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.
The Ramsey Hotel & Convention Center
Downtown Pigeon Forge
Price was $760, price is now $500 per person
$500
per person
Feb 20 - Feb 24
found 1 day ago
Roundtrip flight included
Miami (MIA) to Knoxville (TYS)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
River Terrace Resort & Convention Center
Downtown Gatlinburg
Price was $920, price is now $579 per person
$579
per person
Mar 26 - Mar 30
found 1 day ago
Roundtrip flight included
Miami (MIA) to Knoxville (TYS)
An outdoor pool, free self parking, and laundry facilities are featured at this resort. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A business center, express check-out, and concierge services are also on offer.
River Edge Inn
Downtown Gatlinburg
Price was $815, price is now $570 per person
$570
per person
Mar 26 - Mar 30
found 1 day ago
Roundtrip flight included
Miami (MIA) 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 Oliver Hotel
Downtown Knoxville
Price was $1,039, price is now $744 per person
$744
per person
Feb 19 - Feb 22
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 Resort at Governor's Crossing
Governor’s Crossing
Price was $871, price is now $645 per person
$645
per person
Mar 20 - Mar 23
found 13 hours ago
Roundtrip flight included
Philadelphia (PHL) to Knoxville (TYS)
Free water park access and an indoor pool are featured at this smoke-free hotel. Bring the family and enjoy the lazy river, free kid's club, and mini golf. Enjoy the gym and perks like free self parking and free WiFi.
Top Middlesboro hotels deals
Holiday Inn Express Middlesboro by IHG
1252 N 12th St Middlesboro KY
Free Cancellation
$114 nightly
The price is $126 total per night
$126 total
Jan 18 - Jan 19
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
Sleep Inn & Suites Middlesboro
1260 N, 12th Street Middlesboro KY
Free Cancellation
$94 nightly
The price is $103 total per night
$103 total
Feb 8 - Feb 9
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
Boone Trail Inn
2105 US HIGHWAY 25 E Middlesboro KY
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $84 total per night
$84 total
Jan 19 - Jan 20
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
Holiday Inn Express Williamsburg by IHG
56 West Highway 92 Williamsburg KY
Free Cancellation
$122 nightly
The price is $136 total per night
$136 total
Feb 2 - Feb 3
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
Super 8 by Wyndham Williamsburg
30 W Highway 92 Williamsburg KY
Free Cancellation
Reserve now, pay when you stay
$57 nightly
The price is $63 total per night
$63 total
Jan 19 - Jan 20
Total with taxes and fees
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A business center, a garden, and a picnic area 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
$78 nightly
The price is $86 total per night
$86 total
Jan 21 - Jan 22
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
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.
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.
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