Middlesboro Holidays from £891

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Your Middlesboro Holiday

From its rich history to its spectacular views and beyond, there's a lot to like about Middlesboro. Discover the wonders of this interesting city with a Middlesboro holiday package that's made for you. If taking in sights is on the agenda during your trip to Middlesboro, check out popular attractions like Cumberland Gap National Historical Park, Middlesboro Mall and Bell County Historical Society Museum. Your ideal Middlesboro holiday is just clicks away. Browse accommodation, flights and more on Expedia for an adventure that's tailored to suit your travel style.

Top Middlesboro Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Viewpoint Condominiums

Viewpoint Condominiums

3.5 out of 5
per person
1 Sept - 6 Sept
found 9 hours ago
Return direct flight included
London (LHR) to Knoxville (TYS)
8.8/10 Excellent! (235 reviews)
We really enjoyed our stay.. wish we could have stayed longer. The condos are in the perfect location. Everything from food to fun was in close proximity.

Reviewed on 5 Jul 2025

Club Wyndham Smoky Mountains

Club Wyndham Smoky Mountains

3 out of 5
per person
1 Sept - 6 Sept
found 9 hours ago
Return direct flight included
London (LHR) to Knoxville (TYS)
8.8/10 Excellent! (581 reviews)
Everything was great but did find a roach in the room and notified the hotel and was promised a gift card for our troubles. Other than that it was a lovely experience

Reviewed on 21 May 2025

Sunrise Ridge Resort

Sunrise Ridge Resort

3 out of 5
per person
1 Sept - 6 Sept
found 9 hours ago
Return direct flight included
London (LHR) to Knoxville (TYS)
9/10 Wonderful! (1,007 reviews)
The two bedroom is amazing if you are traveling with kids. I recommend this stay however I did not like that they were always trying to sell me a credit card or timeshare.

Reviewed on 3 Jul 2025

The Ramsey Hotel & Convention Center

The Ramsey Hotel & Convention Center

3 out of 5
Downtown Pigeon Forge
per person
1 Sept - 6 Sept
found 9 hours ago
Return direct flight included
London (LHR) to Knoxville (TYS)
8.4/10 Very Good! (1,196 reviews)
The staff were excellent! They said all the rooms were remodeled but they were basically just painted over and not a good paint job either! First room we had the AC unit didnt work got put into another room where they had just fixed it! Others had issues as well! For the amount of $ we could have stayed in something better

Reviewed on 11 Jul 2025

Hummingbird Hill Vista- Pool HotTub View

Hummingbird Hill Vista- Pool HotTub View

5 out of 5
per person
1 Sept - 6 Sept
found 9 hours ago
Return direct flight included
London (LHR) to Knoxville (TYS)
10/10 Exceptional! (3 reviews)
Game room, hot tub, theater room

Reviewed on 30 Nov 2024

Middlesboro Essential Information

Language
English
Currency
U.S dollars
Population
10,700
Max Temp Winter
7ºC
Max Temp Summer
29ºC
Top Sights
Pine Mountain State Resort Park, Bell County Historical Society Museum and Middlesboro Mall

Top hotels in Middlesboro

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 £70 per night from 20 Jul to 21 Jul
£70
20 Jul - 21 Jul
includes taxes & fees
7/10 Good! (403 reviews)
"Average hotel"

Reviewed on 9 Jul 2025

Econo Lodge 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 £88 per night from 27 Jul to 28 Jul
£88
27 Jul - 28 Jul
includes taxes & fees
9.2/10 Wonderful! (747 reviews)
"Staff was excellent! Breakfast was great with good options. Will definitely stay here again."

Reviewed on 7 Jul 2025

Sleep Inn & Suites
Holiday Inn Express Middlesboro by IHG
Holiday Inn Express Middlesboro by IHG
2.5 out of 5
1252 N 12th St, Middlesboro, KY
Fully refundable
The price is £112 per night from 27 Jul to 28 Jul
£112
27 Jul - 28 Jul
includes taxes & fees
9.4/10 Exceptional! (660 reviews)
"We were there for my mother’s funeral and the staff went out of their way to comfort us."

Reviewed on 9 Jul 2025

Holiday Inn Express Middlesboro by IHG
See all 326 properties in Middlesboro
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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

Why should I book my Middlesboro holiday with Expedia?
Expedia has you covered for all aspects of your upcoming Middlesboro trip. You'll always get the best prices, but when you bundle your flights, hotel and/or hire car into a holiday package, you'll get even bigger savings. Want to truly make the most of your adventure? Add some exciting tours and activities to your customised package. Expedia offers flexible cancellation policies on almost all bookings, so there's no need to worry if your travel plans change. Head over to our Customer Service Portal link to learn more.
When is the best time of year to holiday in Middlesboro?
Middlesboro gets busy in April, July and September. If you're not into big crowds and prefer a slower pace, lock in your escape for December, January and February. With daytime average temperatures of 1ºC, January is the coolest period in Middlesboro. The warmest month is July, when you can experience average temperatures of 24ºC throughout the day. Whatever the weather conditions, you'll find plenty of things to keep you entertained here.
What is the top hotel for my holiday in Middlesboro?
Offering many of the creature comforts of home, Sleep Inn & Suites will make the ideal base for your Middlesboro trip.
How do I get a cheap holiday to Middlesboro?
One of the simplest ways to save money (and time) is to combine your bookings with Expedia. Flights, hotels, activities and hire cars --- we've got them all covered. Select a combination that suits you and watch your savings pile up. We know holidays are never a one-size-fits-all. That's why Expedia offers over 400 airlines and 321,000 hotel options worldwide, so you can customise your Middlesboro holiday your way. Learn more about how you can save money on your next holiday when you combine your hotel and flight bookings with Expedia.
What is the best area to stay in when on holiday in Middlesboro?
Middlesboro has many popular places to explore, like Cumberland Gap National Historical Park. Stay someplace nearby and make sightseeing a breeze.
Do I need a visa for my Middlesboro holiday?
Official government websites are the best source of information on visa requirements, application procedures and any supporting documentation. Your nationality and reason for travelling, whether it be for tourism or business, will determine if you need a visa for Middlesboro. Also double-check that your passport is up to date and has a minimum of six months validity remaining beyond your date of return. Do all your travel planning well ahead of time to avoid any last-minute surprises.
What should I wear on my Middlesboro holiday?
Do a little research into the sorts of things people in Middlesboro wear, and maybe even look up fashion pages on social media for inspiration. You'll want to create a versatile wardrobe full of pieces that work for your destination and showcase your personal style. Take a look at the local weather forecast so you can pack appropriately. The warmest month in Middlesboro is July, with average daily temperatures of 24ºC. If you're holidaying in the coolest month of January, the mercury averages 1ºC during the day.
What does an Expedia Middlesboro holiday include?
It depends on what sort of getaway you're planning. Middlesboro travel deals can include hotels, car hires and flights. You can mix and match to create the package that fits your needs. You can also add on activities and experiences after you've booked to land even bigger discounts. Explore a large range of property types and choose one that fits your group size. The most popular rentals here are hotels and private holiday homes. With Expedia, it's a breeze to tailor-make your Middlesboro escape however you want.
Does Expedia offer Book Now, Pay Later Middlesboro holidays?
Expedia has partnered with online lender Klarna to make booking your next trip a little easier on the wallet. Paying in instalments means you can spread the costs of your next dream escape, leaving you with more cash to play with while you're away. Klarna has several payment plans to choose from, so you're sure to find something that fits your budget. Browse these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month is something that would work for you, Klarna can help. Paying in convenient monthly instalments will make your getaway dreams come true.
  • No-deposit holidays: Clicking the "book now" button is much easier with this option. With no deposit required for your getaway, you can Book Now, Pay Later and get on your way.

Can I choose my airline with a Middlesboro Expedia holiday?
You can. We have more than 400 airline partners worldwide, so choose the carrier that suits your budget needs.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.