Middlesboro Holidays

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Middlesboro Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Wild Bear Inn
Blue Mountain Mist Country Inn & Spa
Compass Hotel by Margaritaville
Sunrise Ridge Resort
Moonshine Holler
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Top hotels in Middlesboro

Sleep Inn & Suites
Sleep Inn & Suites
2.5 out of 5
1260 N, 12th Street, Middlesboro, KY
Fully refundableReserve now, pay when you stay
The price is S$130 per night from 15 Dec to 16 Dec
S$130
includes taxes & fees
15 Dec - 16 Dec
9/10 Wonderful! (652 reviews)
"The hotel had a beautiful view. The room was very clean and the bed was really comfortable. The continental breakfast was really good and all the staff were friendly and helpful. We would definitely stay here again!"

Reviewed on 21 Nov,2024

Sleep Inn & Suites
Econo Lodge Middlesboro
Econo Lodge Middlesboro
2 out of 5
1623 Cumberland Avenue, Middlesboro, KY
Fully refundableReserve now, pay when you stay
The price is S$124 per night from 2 Dec to 3 Dec
S$124
includes taxes & fees
2 Dec - 3 Dec
6.8/10 (351 reviews)
"Decent hotel"

Reviewed on 24 Nov,2024

Econo Lodge Middlesboro
Holiday Inn Express Williamsburg, an IHG Hotel
Holiday Inn Express Williamsburg, an IHG Hotel
2.5 out of 5
56 West Highway 92, Williamsburg, KY
Fully refundable
The price is S$189 per night from 1 Dec to 2 Dec
S$189
includes taxes & fees
1 Dec - 2 Dec
9/10 Wonderful! (869 reviews)
"Great place!!!"

Reviewed on 24 Nov,2024

Holiday Inn Express Williamsburg, an IHG Hotel
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.

Frequently asked questions

How much does a Middlesboro holiday package cost?
Handcraft your Middlesboro holiday package from just S$865. Pick from any combination of flights, hotels and rental cars to pull together the getaway you’ve been dreaming of. Don’t forget to add on a few activities!
How do I get a cheap travel package to Middlesboro?
Our Middlesboro holiday packages promise plenty of savings for the savvy wanderer. For the best deal, simply bundle your hotel, flights and extras (such as activities) into a budget-friendly package. But bargain prices are just the beginning of your next memorable adventure. Book with Expedia and you’ll have more than 550 airlines and 1,000,000 properties around the world to pick from. No matter your budget or style, there’s a package to suit you.
Where should I stay in Middlesboro?
You’ll want to stay where the action is. Many visitors like to book hotels within easy reach of top sights, like Middlesboro Mall, Bell County Historical Society Museum and Middlesboro ARH Hospital.
What are the top hotels in Middlesboro?
Boone Trail Inn and Suburban Studios Middlesboro are a couple of the most popular properties in Middlesboro. Why not have a look at the rates and facilities at each and then decide?
How far in advance should I book my Middlesboro holiday?
You’ll be rewarded with the widest variety at the lowest prices by booking your Middlesboro adventure early. Air carriers generally publish flights around a year in advance, so start locking things in as soon as possible. That being said, Expedia is committed to giving you the best bargains around, so there’s never a bad time to book your dream holiday!
What does an Expedia Middlesboro travel package include?
Hotels, flights and rental cars — we have them covered. With Expedia, you can shape your Middlesboro package the way you like it. All you have to do is determine just what you need. Once you’ve made your booking, you can add on fun things like tours and activities. The more you bundle, the greater your savings!
What should I know before booking a Middlesboro travel package?
Locking in all the parts of your escape together is a simple way to save. Bundle your car rentals, airfares and hotels into a handy little package. But your options don’t end at hotels. Expedia offers all types of properties, including holiday rentals such as beach villas and spacious residences. The list is almost endless!
Can I choose my airline with a Middlesboro Expedia holiday package?
Yes, so take your pick! Expedia has access to more than 550 partner airlines around the world, so you can customize your Middlesboro holiday according to your travel preferences.
If I'm not able to travel, can I cancel my Middlesboro holiday package?
Don’t worry if you’re rethinking your Middlesboro holiday package — it’s possible to change or amend your booking. And if you’ve booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur a fee from your hotel, airline or car rental company. We totally understand life can occasionally throw a spanner in the travel works, so head to our Customer Service Portal if that occurs. When you’re ready to make changes, we’ll take care of it.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.