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
Price was $728, price is now $496 per person
$496
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
Smith Creek Reserve Luxury Cabins
Save 100% on your flight
Price was $6,139, price is now $4,049 per person
$4,049
per person
Jun 1 - Jun 5
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Knoxville (TYS)
2 hot tubs, an indoor pool, and a lazy river are all featured at this luxury cabin. There's fun for all ages with free water park access and a children's pool, and barbecue grills are available on site. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi.
The Ramsey Hotel and Convention Center Pigeon Forge
Downtown Pigeon Forge
Price was $988, price is now $695 per person
$695
per person
Jun 24 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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.
Hotel Indigo Gatlinburg Downtown by IHG
Downtown Gatlinburg
Price was $1,072, price is now $764 per person
$764
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Knoxville (TYS)
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a gym. Relax with a drink at the bar/lounge and enjoy perks like free WiFi. Self parking and a coffee shop are also offered on site.
Redesigned, Hot Tub, Firepit, Billiards Pigeon Forge Riverbend by Avantstay
Save 100% on your flight
Price was $2,748, price is now $1,981 per person
$1,981
per person
Jun 24 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Knoxville (TYS)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.
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
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
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
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 10 - May 11
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
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
Pine Mountain State Resort Park
1050 State Park Road Pineville KY
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $121 total per night
$121 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
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.
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