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.
Sunrise Ridge Resort
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
River Terrace Resort & Convention Center
Downtown Gatlinburg
Save 100% on your flight
per person
Oct 23 - Oct 28
found 1 day ago
Roundtrip flight included
Sacramento (SMF) 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.
Westgate Smoky Mountain Resort & Water Park
Save 100% on your flight
per person
Oct 19 - Oct 24
found 1 day 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.
Courtyard by Marriott Gatlinburg Downtown
per person
Oct 19 - Oct 24
found 2 days 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.
The Oliver Hotel
Downtown Knoxville
per person
Oct 19 - Oct 24
found 2 days ago
Roundtrip non-stop 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.
Top Middlesboro hotels deals
Sleep Inn & Suites
1260 N, 12th Street, Middlesboro, KY
Free Cancellation
Reserve now, pay when you stay
$94 nightly
The price is $103 total per night
$103 total
Aug 31 - Sep 1
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
Econo Lodge Middlesboro
1623 Cumberland Avenue, Middlesboro, KY
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $93 total per night
$93 total
Aug 24 - Aug 25
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
Holiday Inn Express Middlesboro by IHG
1252 N 12th St, Middlesboro, KY
Free Cancellation
$111 nightly
The price is $122 total per night
$122 total
Aug 24 - Aug 25
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
$125 nightly
The price is $139 total per night
$139 total
Aug 24 - Aug 25
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
Days Inn by Wyndham Jellico - Tennessee State Line
1417 5th Street, Jellico, TN
Free Cancellation
Reserve now, pay when you stay
$61 nightly
The price is $70 total per night
$70 total
Aug 19 - Aug 20
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
Pine Mountain State Resort Park
1050 State Park Road, Pineville, KY
Free Cancellation
Reserve now, pay when you stay
$95 nightly
The price is $105 total per night
$105 total
Aug 24 - Aug 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
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 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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