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.
River Terrace Resort & Convention Center
Downtown Gatlinburg
Save 100% on your flight
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Syracuse (SYR) 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
Aug 3 - Aug 9
found 6 hours ago
Roundtrip non-stop flight included
Cedar Rapids (CID) 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.
Sunrise Ridge Resort
per person
Aug 3 - Aug 9
found 6 hours ago
Roundtrip non-stop flight included
Cedar Rapids (CID) 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.
Fireflies and Moonshine
Save 100% on your flight
per person
Jun 12 - Jun 15
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Knoxville (TYS)
This chalet doesn't skimp on freebies - guests receive free WiFi and free self parking. Express check-in, laundry facilities, and barbecue grills are also on offer.
Gatlinburg Town Square by Exploria Resorts
per person
Aug 3 - Aug 9
found 6 hours ago
Roundtrip non-stop flight included
Cedar Rapids (CID) 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 hot tub on site, and laundry facilities and concierge services are also offered.
Top Middlesboro hotels deals
Sleep Inn & Suites
1260 N, 12th Street, Middlesboro, KY
Free Cancellation
Reserve now, pay when you stay
$104 nightly
The price is $114 total per night
$114 total
May 27 - May 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
Econo Lodge Middlesboro
1623 Cumberland Avenue, Middlesboro, KY
Free Cancellation
Reserve now, pay when you stay
$92 nightly
The price is $101 total per night
$101 total
May 18 - May 19
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
May 18 - May 19
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
Boone Trail Inn
2105 US HIGHWAY 25 E, Middlesboro, KY
Free Cancellation
Reserve now, pay when you stay
$81 nightly
The price is $90 total per night
$90 total
May 16 - May 17
Total includes 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
Suburban Studios Middlesboro
1623 Cumberland Avenue Building B, Middlesboro, KY
Free Cancellation
Reserve now, pay when you stay
$104 nightly
The price is $114 total per night
$114 total
Jun 10 - Jun 11
Total includes taxes and fees
A restaurant and a seasonal outdoor pool are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.
Pool
Breakfast included
Holiday Inn Express Williamsburg by IHG
56 West Highway 92, Williamsburg, KY
Free Cancellation
$123 nightly
The price is $139 total per night
$139 total
May 18 - May 19
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
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.
Photos of local treasures
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