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
Price was $831, price is now $542 per person
$542
per person
Nov 2 - Nov 7
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) 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.
Mountain Meadows
Save 100% on your flight
Price was $1,247, price is now $829 per person
$829
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Knoxville (TYS)
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this aparthotel. A lobby fireplace, a picnic area, and barbecue grills are also on offer.
Hotel Indigo Gatlinburg Downtown by IHG
Downtown Gatlinburg
Price was $1,175, price is now $835 per person
$835
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Knoxville (TYS)
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a gym. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. A bar/lounge, a 24-hour front desk, and a coffee shop are also provided.
Laurel Point Resort
Chalet Village
Price was $957, price is now $689 per person
$689
per person
Nov 1 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) 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.
Westgate Smoky Mountain Resort & Water Park
Price was $948, price is now $688 per person
$688
per person
Oct 22 - Oct 25
found 5 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Knoxville (TYS)
A full-service spa, 3 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Enjoy the 2 hot tubs and perks like free WiFi. 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
$108 nightly
The price is $119 total per night
$119 total
Sep 21 - Sep 22
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
$135 nightly
The price is $149 total per night
$149 total
Aug 23 - Aug 24
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
$89 nightly
The price is $98 total per night
$98 total
Aug 30 - Aug 31
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
$78 nightly
The price is $86 total per night
$86 total
Sep 13 - Sep 14
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
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 31 - Sep 1
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
Pine Mountain State Resort Park
1050 State Park Road Pineville KY
Free Cancellation
Reserve now, pay when you stay
$170 nightly
The price is $187 total per night
$187 total
Aug 28 - Aug 29
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.
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