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 Timber at Holly Branch
Price was $858, price is now $661 per person
$661
per person
May 25 - May 28
found 16 hours ago
Roundtrip non-stop flight included
Columbus (CMH) to Knoxville (TYS)
This hotel features a coffee shop, concierge services, and free self parking. WiFi in public areas is free. A lobby fireplace, a communal living room, and express check-out are also on offer.
River Terrace Resort & Convention Center
Downtown Gatlinburg
Price was $996, price is now $700 per person
$700
per person
May 21 - May 25
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) 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.
Holiday Inn Club Vacations Smoky Mountain Resort by IHG
Price was $933, price is now $702 per person
$702
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Knoxville (TYS)
2 hot tubs, an outdoor pool, and an indoor pool are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and a waterslide, and families will appreciate the onsite laundry facilities. You'll appreciate the area shuttle, 24-hour business center, and garden.
Cumberland House Knoxville, Tapestry Collection by Hilton
Downtown Knoxville
Price was $1,052, price is now $804 per person
$804
per person
Jun 5 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Knoxville (TYS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Dry cleaning, luggage storage, and laundry facilities are also on offer.
The Oliver Hotel
Downtown Knoxville
Price was $1,150, price is now $880 per person
$880
per person
Jun 5 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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 Middlesboro
1260 N, 12th Street Middlesboro KY
Free Cancellation
$95 nightly
The price is $105 total per night
$105 total
May 10 - May 11
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
$127 nightly
The price is $140 total per night
$140 total
Apr 19 - Apr 20
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
$80 nightly
The price is $88 total per night
$88 total
Apr 19 - Apr 20
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
Suburban Studios Middlesboro
1623 Cumberland Avenue Building B Middlesboro KY
Free Cancellation
Reserve now, pay when you stay
$84 nightly
The price is $93 total per night
$93 total
May 6 - May 7
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
Pine Mountain State Resort Park
1050 State Park Road Pineville KY
Free Cancellation
Reserve now, pay when you stay
$108 nightly
The price is $119 total per night
$119 total
Apr 18 - Apr 19
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
Super 8 by Wyndham Williamsburg
30 W Highway 92 Williamsburg KY
$68 nightly
The price is $76 total per night
$76 total
Apr 19 - Apr 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
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 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.
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
Photos of local treasures
Browse Middlesboro vacation photos for more inspiration
