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.
Gatlinburg Town Square
Price was $1,021, price is now $732 per person
$732
per person
May 19 - May 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Knoxville (TYS)
This hotel features an indoor pool and a gym. There's fun for all ages with a children's pool and a playground, 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
Price was $2,259, price is now $1,514 per person
$1,514
per person
Apr 14 - Apr 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Hilton Knoxville
Downtown Knoxville
Save 100% on your flight
Price was $1,647, price is now $1,158 per person
$1,158
per person
Apr 10 - Apr 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Knoxville (TYS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. There's a seasonal outdoor pool on site, and a 24-hour front desk and a coffee shop are also provided.
Holiday Inn Express Gatlinburg Downtown by IHG
Save 100% on your flight
Price was $1,493, price is now $1,090 per person
$1,090
per person
May 19 - May 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Knoxville (TYS)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. There's an indoor pool on site, and a 24-hour front desk and a snack bar/deli are also provided.
The Ramsey Hotel & Convention Center
Downtown Pigeon Forge
Price was $1,070, price is now $788 per person
$788
per person
May 20 - May 25
found 21 hours ago
Roundtrip flight included
Detroit (DTW) 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.
Top Middlesboro hotels deals
Sleep Inn & Suites Middlesboro
1260 N, 12th Street Middlesboro KY
Free Cancellation
$105 nightly
The price is $115 total per night
$115 total
Mar 15 - Mar 16
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
Suburban Studios Middlesboro
1623 Cumberland Avenue Building B Middlesboro KY
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $83 total per night
$83 total
Mar 15 - Mar 16
Total with 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
Boone Trail Inn
2105 US HIGHWAY 25 E Middlesboro KY
Free Cancellation
Reserve now, pay when you stay
$79 nightly
The price is $88 total per night
$88 total
Mar 2 - Mar 3
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
Super 8 by Wyndham Williamsburg
30 W Highway 92 Williamsburg KY
Free Cancellation
Reserve now, pay when you stay
$68 nightly
The price is $76 total per night
$76 total
Mar 3 - Mar 4
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
Holiday Inn Express Williamsburg by IHG
56 West Highway 92 Williamsburg KY
Free Cancellation
$131 nightly
The price is $146 total per night
$146 total
Mar 22 - Mar 23
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
Days Inn by Wyndham Jellico - Tennessee State Line
1417 5th Street Jellico TN
Free Cancellation
Reserve now, pay when you stay
$59 nightly
The price is $67 total per night
$67 total
Mar 8 - Mar 9
Total with 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
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.
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.
Frequently asked questions
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