Top Middlesboro Hotel Deals

Make the Most of Your Middlesboro Stay

A city built inside a meteor crater

Middlesboro occupies one of America's most unusual settings—the entire city sits within a 3-mile-wide meteorite impact crater formed 300 million years ago. This geological distinction earned it the nickname "Crater City," though locals also remember its ambitious origins as the "Magic City," when Scottish entrepreneur Alexander Arthur founded it in 1886 with dreams of creating the "Pittsburgh of the South." The historic downtown preserves Victorian-era architecture from that boom period, while the surrounding crater rim creates a natural amphitheater effect that's immediately noticeable.

Gateway to American history

The city's location at the western edge of Cumberland Gap National Historical Park places you at one of the most significant passages in American westward expansion. Daniel Boone and over 300,000 pioneers crossed through this mountain gap between 1775 and 1810, and today you can stand at the Pinnacle Overlook viewing 3 states simultaneously. The nearby Abraham Lincoln Library and Museum houses one of the country's largest Lincoln collections, while Middlesboro Country Club, established in 1889, claims the title of America's oldest continuously played golf course.

Practical considerations

A rental car is essential, with most visitors flying into Knoxville's McGhee Tyson Airport 90 minutes south. The compact downtown and proximity to natural attractions make Middlesboro an efficient base for exploring southeastern Kentucky.

Frequently Asked Questions about Middlesboro

Can I use my miles on Delta Stays to book hotels in Middlesboro?

Yes, you can book your hotel stay in Middlesboro using your Delta miles, or a combination of miles and cash. Simply log in to your SkyMiles® account, where you will also discover Member-only offers at select properties that could enhance your travel experience.

What is the benefit of booking my Middlesboro hotel directly on Delta Stays?

As a SkyMiles Member, you will earn 2 miles per $1 you spend on completed hotel stays and vacation rentals booked through Delta Stays. You will also enjoy access to special Member offers at select properties, and have the flexibility to pay with miles, cash, or a combination of both. To receive your miles, make sure to log in to your SkyMiles account or provide your SkyMiles number during checkout when making a cash payment. Please allow up to 8 weeks after completing a stay for miles to appear in the SkyMiles account provided. Please also note that if you use miles to pay for any portion of your stay, you will not earn miles on that reservation, including any amount paid with cash.

Is it possible to change or cancel my hotel booking made through Delta Stays?

Cancellation policies differ depending on the property you choose. We recommend reviewing the cancellation terms displayed in the property information section before confirming your reservation. You will notice that refundable options are available for some rates, while others may be non-refundable. Any modifications or cancellations to your reservation may affect the mileage credits you earn and receive in your account.

Can I use my Delta SkyMiles® American Express® Card to book?

Your Delta SkyMiles® Gold, Platinum, or Reserve American Express® Card offers enhanced mileage earning potential along with a suite of benefits, including an annual statement credit up to $200 that can be utilized for prepaid accommodations when booking through Delta Cars and Stays. Terms apply to these offers. To gain a full understanding of your card's complete benefits package, we recommend visiting the Delta SkyMiles® American Express Credit Cards page where detailed information about all your cardholder privileges is available for review.

Can I earn MQDs on Delta Stays hotel bookings?

Delta Stays occasionally offers valued promotions allowing SkyMiles Members to accumulate Medallion® Qualification Dollars when booking accommodations through their platform. We encourage you to visit the Delta Stays MQD Offer page to check for the latest MQDs offers and review their specific terms and conditions.

Do I need to have a Delta SkyMiles account to book hotels on Delta Stays?

Delta Stays provides hotel booking services to all customers. However, registering as a SkyMiles Member enhances your experience by allowing you to earn miles and access Member pricing and promotions. As a Member, you will earn 2 miles per $1 you spend on Delta Cars and Stays (excluding taxes and other fees). The best part is that SkyMiles is free to join. Register today by going to the delta.com.

On Delta Stays, can I book a vacation rental?

Yes, Delta Stays extends beyond conventional hotel offerings to include a wide selection of vacation rentals for your travel accommodations. Explore the variety of homes, condos, and unique accommodations powered by Vrbo on the Vacation Rentals page.

What's a good time of year to visit Middlesboro?

To experience Middlesboro during great weather, consider a visit in June when temperatures are warm and ideal for exploring Cumberland Gap National Historical Park. For off-peak prices and more deals on hotels, consider visiting during January when temperatures are cooler with fewer visitors and lower pricing.

*Terms and conditions:

Mileage Offer:

SkyMiles Members will earn two (2) miles per US$1 or equivalent foreign currency spent at https://carsandstays.delta.com/Opens in a new window on the base hotel rate for a completed hotel stay. Base hotel rate is the cost of the hotel room, before taxes and fees, charged at the time of booking or upon checkout. Taxes and fees, gratuities, room service other booking charges, or any bookings which are paid or reduced by miles, redemption vouchers or discount codes are excluded from mileage credit. For clarity, if miles are used as a form of payment (whether for all or a portion of the booking), no portion of the booking will be eligible to earn miles under this offer. Except with respect to the Hertz Mileage offer (listed below), SkyMiles Members will earn two (2) miles per eligible US$1 or equivalent foreign currency spent at https://carsandstays.delta.com/Cars on the base car rental rate for a completed car qualifying rental booking (“Qualifying Dollars”). A qualifying rental booking includes rentals at a participating location for one or more days at rates other than travel industry rates or discounts, wholesale of tour package rates or discounts, wholesale tour package rates, insurance/dealer replacement rates, corporate and government rates, group travel discounts, or rentals in conjunction with a frequent flyer car award, or other corporate agreements applicable to the respective car company. Calculation of the applicable standard mileage offer is listed below by car rental company. Qualifying Dollars include the base car rental rate, which is the cost of the car rental before taxes and fees, charged at the time of booking. Taxes, fees, other incidental charges, or other booking charges or any bookings which are paid or reduced by redemption vouchers or discount codes are excluded from mileage credit and are not included in the Qualifying Dollars.

This mileage offer does not apply to stays or car rentals booked through Delta Vacations or any cruises booked through Delta Cruises.

Standard mileage offer for car rentals booked at https://www.delta.com/Opens in a new window or https://carsandstays.delta.com/Opens in a new window:

Hertz Reservations:

• General SkyMiles Members earn 4 miles per Qualifying Dollar

• Silver Medallions earn 5 miles per Qualifying Dollar

• Gold Medallions earn 6 miles per Qualifying Dollar

• Platinum Medallions earn 7 miles per Qualifying Dollar

• Diamond Medallions earn 8 miles per Qualifying Dollar

Dollar and Thrifty Reservations:

• All SkyMiles Members earn 4 miles per Qualifying Dollar

Alamo, Enterprise, National, Avis, Budget, Payless and SIXT Reservations:

• All SkyMiles Members earn 2 miles per Qualifying Dollar