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 $529, price is now $405 per person
$405
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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. Guests will appreciate free perks like free self parking and WiFi in public areas.
Laurel Point Resort
Chalet Village
Save 100% on your flight
Price was $799, price is now $513 per person
$513
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Knoxville (TYS)
This aparthotel features an indoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. There's a sauna on site, and laundry facilities and barbecue grills are also offered.
Holiday Inn Express Gatlinburg Downtown by IHG
Price was $586, price is now $430 per person
$430
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
Holiday Inn Club Vacations Smoky Mountain Resort by IHG
Price was $853, price is now $632 per person
$632
per person
Sep 10 - Sep 14
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.
Hilton Garden Inn Gatlinburg
Downtown Gatlinburg
Price was $759, price is now $594 per person
$594
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Knoxville (TYS)
This hotel features an outdoor pool, an indoor pool, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. You'll appreciate the gym, bar/lounge, and laundry facilities.
Top Middlesboro hotels deals
Sleep Inn & Suites Middlesboro
1260 N, 12th Street Middlesboro KY
Free Cancellation
$103 nightly
The price is $114 total per night
$114 total
Aug 2 - Aug 3
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
$82 nightly
The price is $90 total per night
$90 total
Aug 6 - Aug 7
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
$135 nightly
The price is $149 total per night
$149 total
Aug 6 - Aug 7
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
Days Inn by Wyndham Jellico - Tennessee State Line
1417 5th Street Jellico TN
Free Cancellation
Reserve now, pay when you stay
$61 nightly
The price is $70 total per night
$70 total
Jul 27 - Jul 28
Total with taxes and fees
A full-service spa, 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. Staff at the 24-hour front desk can provide around-the-clock assistance.
Breakfast included
Spa
Holiday Inn Express Williamsburg by IHG
56 West Highway 92 Williamsburg KY
Free Cancellation
$110 nightly
The price is $122 total per night
$122 total
Aug 3 - Aug 4
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
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.
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