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

Laurel Point Resort

2.5 out of 5
Chalet Village
Price was $806, price is now $584 per person
$584
per person
Aug 27 - Aug 31
found 5 hours ago
Roundtrip flight included
Dallas (DFW) 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.
Mountain Meadows

Mountain Meadows

2.5 out of 5
Price was $841, price is now $602 per person
$602
per person
Sep 9 - Sep 14
found 13 hours ago
Roundtrip flight included
Dallas (DFW) 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.
The Ramsey Hotel and Convention Center Pigeon Forge

The Ramsey Hotel and Convention Center Pigeon Forge

3 out of 5
Downtown Pigeon Forge
Price was $814, price is now $585 per person
$585
per person
Sep 9 - Sep 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Holiday Inn Express Gatlinburg Downtown by IHG

Holiday Inn Express Gatlinburg Downtown by IHG

2.5 out of 5
Price was $905, price is now $657 per person
$657
per person
Sep 26 - Oct 1
found 22 hours ago
Roundtrip flight included
Dallas (DAL) 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.
Margaritaville Island Hotel

Margaritaville Island Hotel

4 out of 5
Downtown Pigeon Forge
Save 100% on your flight
Price was $1,179, price is now $866 per person
$866
per person
Sep 26 - Oct 1
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Knoxville (TYS)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this hotel. Enjoy the outdoor pool and perks like free WiFi. Enjoy the gym and unwind at the bar/lounge and poolside bar.

Top Middlesboro hotels deals

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

2.5 out of 5
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

Econo Lodge Middlesboro

2 out of 5
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

Holiday Inn Express Middlesboro by IHG

2.5 out of 5
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

Days Inn by Wyndham Jellico - Tennessee State Line

2 out of 5
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

Holiday Inn Express Williamsburg by IHG

2.5 out of 5
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

Super 8 by Wyndham Williamsburg

2.5 out of 5
30 W Highway 92 Williamsburg KY
Get rates
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
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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.

Stay near popular Middlesboro attractions

Middlesboro Mall

7.6/10 (62 reviews)
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.
See properties

Frequently asked questions

How much are vacation packages to Middlesboro?
Travelocity provides package deals to Middlesboro, including flights and hotels, from an impressive $584. With all the extra money, you could book some popular tours or possibly even add some extra nights to your adventure.
How long should my Middlesboro vacation be?
Most people choose to spend about 2 nights in Middlesboro, but how long you stay is totally up to you. If you'd like to venture out and explore all the intriguing things this location has to offer, why not hang around another few nights?
Where can I get the best vacation package deals for Middlesboro?
No matter what you enjoy doing, Travelocity can help you snap up an unbeatable Middlesboro package deal. All you need to do is mix and match from our 400 partner airlines and 1,000,000 worldwide properties.
Why should I purchase my Middlesboro vacation package via Travelocity?
With our Price Match Guarantee, we'll match any better price you find. Add on our 24/7 support and first-rate service and your perfect vacation is closer than ever before.
Will I save money on my Middlesboro car rental if I book it with a hotel or flight?
Bundling your hotel, flight and car into a Middlesboro vacation package is the best way to land the best prices. Plus, having your own car rental gives you freedom to get to all those big-name sights you want to check out. Sitting 55 mi away from Middlesboro, Dollywood is one attraction that should feature on your itinerary. Load up the car and make a day trip of it.
Which airport is best for Middlesboro?
McGhee Tyson Airport (TYS) sits 60 mi south of central Middlesboro.
Where should I stay when visiting Middlesboro?
Many visitors stay at the Holiday Inn Express Middlesboro, an IHG Hotel. It's sure to be a great base for your Middlesboro vacation.

Photos of local treasures

Browse Middlesboro vacation photos for more inspiration

An aerial view of a town surrounded by mountains, with a mix of residential and commercial buildings, and a highway running through the center.
A mountainous landscape with a town nestled in the valley.
A mountainous landscape with a town nestled in the valley, surrounded by dense forests and a winding road.
Stonehenge with standing stones and a large horizontal lintel.
A forest path surrounded by dense green ferns and trees.