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.
Laurel Point Resort
Chalet Village
Price was $892, price is now $637 per person
$637
per person
Nov 13 - Nov 17
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.
River Terrace Resort & Convention Center
Downtown Gatlinburg
Save 100% on your flight
Price was $1,263, price is now $792 per person
$792
per person
Oct 15 - Oct 19
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.
Westgate Smoky Mountain Resort & Water Park
Price was $948, price is now $688 per person
$688
per person
Oct 22 - Oct 25
found 2 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.
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.
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.
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.
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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