Deals on vacations and trips to Middlesboro

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Price found within the past 48 hours. Click for updated prices.
River Terrace Resort & Convention Center

River Terrace Resort & Convention Center

3.5 out of 5
Downtown Gatlinburg
Price was $881, price is now $604 per person
$604
per person
Sep 25 - Sep 28
found 5 hours 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.
Hotel Indigo Gatlinburg Downtown by IHG

Hotel Indigo Gatlinburg Downtown by IHG

3.5 out of 5
Downtown Gatlinburg
Price was $1,248, price is now $904 per person
$904
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
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 $1,000, price is now $734 per person
$734
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Stonebrook Lodge Cherokee

Stonebrook Lodge Cherokee

2.5 out of 5
Price was $1,147, price is now $850 per person
$850
per person
Oct 4 - Oct 11
found 22 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Knoxville (TYS)
This hotel features a seasonal outdoor pool and a hot tub. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
The Copper Bird Cabin

The Copper Bird Cabin

5 out of 5
Save 100% on your flight
Price was $1,774, price is now $1,320 per person
$1,320
per person
Nov 5 - Nov 12
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Knoxville (TYS)
This lodge doesn't skimp on freebies - guests receive free WiFi and free self parking. Express check-out, laundry facilities, and barbecue grills are also on offer.

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
$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.
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
$154 nightly
The price is $170 total per night
$170 total
Aug 30 - Aug 31
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

Econo Lodge Middlesboro

2 out of 5
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

Suburban Studios Middlesboro

2 out of 5
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.
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 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

Pine Mountain State Resort Park

3 out of 5
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.
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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.
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Frequently asked questions

How much are vacation packages to Middlesboro?
Travelocity provides package deals to Middlesboro, including flights and hotels, from an impressive $604. 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.