Deals on vacations and trips to Middlesboro
Save when you book Middlesboro package deals
Middlesboro flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
The Oliver Hotel
Downtown Knoxville
Price was $699, price is now $483 per person
$483
per person
Mar 23 - Mar 26
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) 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
Save 100% on your flight
Price was $1,196, price is now $763 per person
$763
per person
Mar 22 - Mar 28
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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.
Sunrise Ridge Resort
Price was $826, price is now $587 per person
$587
per person
Mar 22 - Mar 28
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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.
The Ramsey Hotel & Convention Center
Downtown Pigeon Forge
Price was $1,052, price is now $756 per person
$756
per person
Mar 22 - Mar 28
found 1 day 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.
Creekstone Inn
Price was $718, price is now $537 per person
$537
per person
Mar 22 - Mar 28
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Knoxville (TYS)
A seasonal outdoor pool is featured at this hotel, along with free self parking. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. Express check-in and express check-out are also provided.
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
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
Holiday Inn Express Middlesboro by IHG
1252 N 12th St Middlesboro KY
Free Cancellation
$125 nightly
The price is $138 total per night
$138 total
Feb 8 - Feb 9
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
Econo Lodge Middlesboro
1623 Cumberland Avenue Middlesboro KY
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $98 total per night
$98 total
Jan 13 - Jan 14
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
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 13 - Jan 14
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 15 - Jan 16
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
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.
Frequently asked questions
Photos of local treasures
Browse Middlesboro vacation photos for more inspiration
