Middlesboro Vacation Packages

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Your Middlesboro Vacation

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 vacation 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 vacation is just clicks away. Browse accommodations, flights and more on Expedia for an adventure that's tailored to suit your travel style.

Top Middlesboro Vacation Deals

Price found within the past 48 hours. Click for updated prices.
River Edge Inn

River Edge Inn

2 out of 5
Downtown Gatlinburg
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Knoxville (TYS)
8.6/10 Excellent! (1,003 reviews)
This was our first stay at River Edge Inn. We were especially impressed with the exceptional staff. Thru were all very friendly and extremely helpful! We noticed there was no cold water in our shower. They sent someone right away to check it. When it couldn’t be repaired right away they offered us another room & made the transition as smooth as possible. The rooms were very spacious. Everything was quite quiet. Breakfast was continental but all items were name brand. Many restaurants close by. We hope to be back!

Reviewed on Jun. 29, 2025

Westgate Smoky Mountain Resort & Water Park

Westgate Smoky Mountain Resort & Water Park

4 out of 5
Save 100% on your flight
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Knoxville (TYS)
8.4/10 Very Good! (1,092 reviews)
This place is so beautiful and so friendly! The building we stayed in was only 2 weeks old so everything was new! We needed extra blankets and all we did was text and it was at our door! Westgate has got it down! Several pools and the onsite restaurant was so good for breakfast and dinner. Definitely will be coming back!!!!

Reviewed on Jun. 18, 2025

Sunrise Ridge Resort

Sunrise Ridge Resort

3 out of 5
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) 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 Jul. 3, 2025

Compass Hotel by Margaritaville

Compass Hotel by Margaritaville

3 out of 5
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Knoxville (TYS)
9.8/10 Exceptional! (1,124 reviews)
This property was amazing. Kayla at the Resturant/bar was wonderful.

Reviewed on Jul. 1, 2025

Club Wyndham Smoky Mountains

Club Wyndham Smoky Mountains

3 out of 5
Save 100% on your flight
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) 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 May 21, 2025

Ready to book your vacation to Middlesboro?

 

Choose your dates

Middlesboro Hotel Deals

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 CA $145 per night from Jul 20 to Jul 21
CA $145
CA $160 total
Jul 20 - Jul 21
includes taxes & fees
9.2/10 Wonderful! (743 reviews)
"Kind staff"

Reviewed on Jun. 30, 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 CA $164 per night from Jul 6 to Jul 7
CA $164
CA $181 total
Jul 6 - Jul 7
includes taxes & fees
9.4/10 Exceptional! (656 reviews)
"Friendly and helpful staff. Breakfast was fresh and good."

Reviewed on Jul. 1, 2025

Holiday Inn Express Middlesboro by IHG
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 CA $116 per night from Jul 13 to Jul 14
CA $116
CA $128 total
Jul 13 - Jul 14
includes taxes & fees
7/10 Good! (401 reviews)
Old but clean and nice
"Could tell old, but very clean and nice. It had everything we needed for our stay."

Reviewed on Jun. 27, 2025

Econo Lodge Middlesboro
See all 320 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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Middlesboro vacation package cost?
You'll find cheap prices from CA $957 on Expedia for your Middlesboro getaway. However, factors like the hotel choice, length of stay and season will influence how much your vacation to Middlesboro costs.
What are the cheapest months to go to Middlesboro?
You can usually find reduced prices and better availability in January, February and November. Check out our cheap Middlesboro vacation packages and you could score some excellent off-season deals.
How many days is enough for Middlesboro?
With a well-planned schedule, you can easily visit the main Middlesboro sights in a handful of days. But if you'd like to discover lesser-known spots or take day trips, think about booking your Middlesboro vacation for longer.
How to find the best Middlesboro package deals?
Start your search for a Middlesboro package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Middlesboro package deal right away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Middlesboro adventure off to a flying start.
Is it cheaper to book a Middlesboro vacation as a package?
You can enjoy significant savings on your next Middlesboro break by booking a personalized vacation package. Check the "Package" heading, then select your travel dates and destination to browse some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Middlesboro?
Enjoy incredible discounts by reserving your flights early with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Middlesboro break.
How to plan a trip to Middlesboro?

  1. Choose your dates: The things you want to do in Middlesboro and your favourite season will help you decide when to go.
  2. Set a budget: Factor in expenses like flights, transportation and food when working out how much to set aside for your trip to Middlesboro. Then, select a hotel that works with your budget, whether that's a wallet-friendly option or a more upscale retreat.
  3. Decide how many days away: Start by compiling a list of the sights and activities you'd like to experience in Middlesboro. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your airfare and accommodations: After you've nailed down your dates and duration, book the ideal Middlesboro vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.