The Best Hotels with Connecting Rooms in Middlesboro from $70 in 2025

Q: Are there any family-friendly hotels with connecting rooms in Middlesboro?

Settle in at Holiday Inn Express Middlesboro, an IHG Hotel , a 2.5-star option just a short drive from downtown. Amenities here include complimentary breakfast and a barbecue grill. Another family-friendly hotel with connecting rooms is Sleep Inn & Suites . Complimentary breakfast and a barbecue grill help make this 2.5-star stay a favorite among guests. Middlesboro has no shortage of family-friendly attractions to visit when the kids are getting restless. Bell County Historical Society Museum and Middlesboro Mall guarantee fun for travelers young and old.

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Top Middlesboro Hotels with Connecting Rooms

Standard Room | Desk, blackout drapes, iron/ironing board, rollaway beds

Holiday Inn Express Middlesboro by IHG

Middlesboro

Harold

$118 nightly

Nov 23 - Nov 24

Total with taxes and fees

Sleep Inn & Suites Middlesboro

Middlesboro

Kay

$94 nightly

Dec 7 - Dec 8

Total with taxes and fees

Standard Room, 2 Double Beds, Non Smoking | Laptop workspace, blackout drapes, iron/ironing board, free WiFi

Econo Lodge Middlesboro

Middlesboro

James

$75 nightly

Nov 18 - Nov 19

Total with taxes and fees

Days Inn by Wyndham Jellico - Tennessee State Line

Jellico

Antoninette

$64 nightly

Dec 1 - Dec 2

Total with taxes and fees

Pine Mountain State Resort Park

Pineville

Andrew

$84 nightly

Nov 18 - Nov 19

Total with taxes and fees

Holiday Inn Express Williamsburg by IHG

Williamsburg

Stacey

$118 nightly

Dec 17 - Dec 18

Total with taxes and fees

Quality Inn

Harlan

James

$92 nightly

Nov 23 - Nov 24

Total with taxes and fees

Suite, Accessible, Ensuite (Thomas Walker Annex) | 1 bedroom, WiFi

The Olde Mill Inn Bed & Breakfast

Cumberland Gap

Michael

$148 nightly

Dec 16 - Dec 17

Total with taxes and fees

View all properties

Find out more about Middlesboro

Discover top Middlesboro attractions

Middlesboro, Kentucky, is brimming with unique attractions that cater to adventurous travelers seeking quality experiences. Start your journey with a visit to the Cumberland Gap National Historical Park, where you can explore scenic trails and enjoy breathtaking views of the Appalachian Mountains. This area is rich in history and offers a perfect backdrop for family hikes or leisurely strolls. Next, check out the Bell County Historical Society, where you can delve into the local culture and history, with exhibits ranging from Native American artifacts to Civil War memorabilia. For a bit of outdoor fun, head to the nearby Pine Mountain State Resort Park, where you can enjoy activities like fishing, horseback riding, and camping, all set within the tranquility of nature. Adventure seekers can also try their hand at zip-lining through the lush canopy at the nearby Adventure Off Road Park. After a day of exploration, consider settling down in the vibrant downtown area, where you’ll find charming local hotels that offer modern amenities and exceptional service. These accommodations provide a cozy home base, making it easy to unwind after a day filled with adventure. With local eateries just a short walk away, you’ll have the chance to indulge in delicious Southern cuisine, enhancing your overall travel experience.

Find the best hotels with connecting rooms in Middlesboro

For travelers seeking convenient accommodations in Middlesboro, Kentucky, these hotels offer connecting room options that make family reunions or group travels a breeze. Each hotel ensures a comfortable stay with essential amenities for families.

Holiday Inn Express Middlesboro by IHG

Why it's great for extra space: Ideal for families or groups needing extra space, the Holiday Inn Express Middlesboro by IHG features connecting rooms, providing a seamless experience for guests. With a stellar review rating of 9.6, this hotel ensures comfort with amenities like free buffet breakfast and an outdoor pool, perfect for unwinding after a day of exploration.
Other amenities: Additional amenities include stunning mountain views, daily housekeeping, and free self-parking. Guests can enjoy a fitness center, onsite microwaves for convenience, and access to nearby hiking and biking trails. The hotel also boasts pool sun loungers for relaxation and offers toiletries at no extra cost.
Nearby attractions: Cumberland Gap National Historical Park - 1.11 miles, Bell County Historical Society Museum - 1.61 miles, Middlesboro Mall - 0.21 miles

Sleep Inn & Suites

Why it's great for extra space: The Sleep Inn & Suites is a great choice for those traveling with family or friends, offering connecting rooms that enhance the communal experience. This hotel has received a review rating of 9.2, reflecting its commitment to guest satisfaction. With features like a complimentary breakfast and free cribs, it caters perfectly to those needing extra space and convenience.
Other amenities: Guests will find additional amenities such as a fitness center, free self-parking, and daily housekeeping. The hotel also provides microwaves in rooms for quick meals, while outdoor parking accommodates RVs and buses. Free toiletries and a sofa bed further ensure a comfortable stay for all guests.
Nearby attractions: Cumberland Gap National Historical Park - 1.33 miles, Bell County Historical Society Museum - 1.54 miles, Middlesboro Mall - 0.35 miles

Econo Lodge Middlesboro

Why it's great for extra space: The Econo Lodge Middlesboro is a budget-friendly option that offers connecting rooms, catering to families or larger groups looking for a comfortable place to stay. With a review rating of 7.2, this hotel provides essential amenities while keeping affordability in mind. Guests can enjoy a free continental breakfast to start their day and access to a shared pool for relaxation.
Other amenities: Additional features include free self-parking and daily housekeeping services. The hotel is situated with scenic mountain views and offers air-conditioned rooms for comfort. Guests can take advantage of the pool sun loungers and the secure pool area, making it a great spot for groups to enjoy leisure time together.
Nearby attractions: Cumberland Gap National Historical Park - 0.37 miles, Bell County Historical Society Museum - 0.52 miles, Middlesboro Mall - 1.14 miles

Top Middlesboro Hotel Reviews

Days Inn by Wyndham Jellico - Tennessee State Line

10/10 Excellent

"The staff was friendly, the room was clean and well stocked, the TV and internet worked great. I would definitely recommend this Days Inn."

Pine Mountain State Resort Park

10/10 Excellent

"We have been to a lot of State Parks over the years and this one might be the best. Great views. The staff and service were amazing, and our cabin was nice and clean. We ate breakfast and dinner at the lodge several times and it was always fantastic. The alcohol menu is really nice, plenty of variety and reasonably priced. They offer more amenities than other parks like borrowing a fishing pole and tackle box for the lake. You can also borrow board games from the game room to take to your room/cabin. The game room also has a ping pong table, a table-size Connect4 game and other cool things. Pet friendly. The hiking trails were clear and labeled well with plenty of signs. We will be visiting again."

Frequently asked questions

How much do hotels with connecting rooms in Middlesboro cost?

The price range for hotels with connecting rooms in Middlesboro is $70 to $168 per night. No matter your budget, you'll find someplace that fits your needs — as well as your entire squad! These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

What are the best hotels with connecting rooms in Middlesboro?

Middlesboro has multiple hotels with connecting rooms with a total average guest review rating of 8.3. Holiday Inn Express Middlesboro, an IHG Hotel comes highly rated if you're traveling with the kids or some friends. Guests of this 2.5-star hotel will have access to pool sun loungers and a swimming pool. Sleep Inn & Suites is another favorite. This 2.5-star hotel offers connecting rooms and also features a barbecue grill and blackout curtains.

How many hotels with adjoining rooms are there in Middlesboro?

Work out your vacation dates and then pick from 3 hotels with adjoining rooms in Middlesboro. For work-related travel, a solo adventure and everything in between, Expedia will help you find your ideal stay in a few simple clicks.

What are the best cheap hotels with connecting rooms in Middlesboro?

Hotels with connecting rooms start from $70 per night, so your Middlesboro break doesn't need to take a big chunk out of your finances! Holiday Inn Express Middlesboro, an IHG Hotel is a pocket-friendly pick that features many amenities, including pool sun loungers and a swimming pool. Sleep Inn & Suites is another of our popular hotels with connecting rooms. Take advantage of conveniences such as a barbecue grill and free WiFi. When it's time to get to know Middlesboro, visit Middlesboro Mall. This cool attraction is free if you're also planning to sightsee on the cheap. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

What are the top motels with connecting rooms in Middlesboro?

Round up the crew and head directly to Econo Lodge Middlesboro. This wallet-friendly motel with connecting rooms also comes with pool sun loungers and blackout curtains, and is conveniently located just 0.5 mi east of Middlesboro's city center.When it's time to slip on your comfiest sneakers and discover your surroundings, head for Bell County Historical Society Museum. Middlesboro Mall is another worthwhile attraction in Middlesboro.

Are there any family-friendly hotels with connecting rooms in Middlesboro?

Settle in at Holiday Inn Express Middlesboro, an IHG Hotel, a 2.5-star option just a short drive from downtown. Amenities here include complimentary breakfast and a barbecue grill. Another family-friendly hotel with connecting rooms is Sleep Inn & Suites. Complimentary breakfast and a barbecue grill help make this 2.5-star stay a favorite among guests. Middlesboro has no shortage of family-friendly attractions to visit when the kids are getting restless. Bell County Historical Society Museum and Middlesboro Mall guarantee fun for travelers young and old.

Why book your hotel with connecting rooms in Middlesboro with Expedia?

Booking a hotel with connecting rooms in Middlesboro is as simple as clicking on your travel dates and picking the option that satisfies your needs. Want something inexpensive or upscale, or a stay that also has a kitchen and laundry? Use Expedia's search filters to further narrow your search results and find your perfect match.

How can I find cheap hotels with connecting rooms in Middlesboro?

With Expedia's useful filter tool, getting your hands on cheap hotels with connecting rooms in Middlesboro has never been easier. To discover properties that'll make your wallet happy, narrow down your search by star rating, amenities and budget.

What is there to do in Middlesboro near my hotel with connecting rooms?

After you've unpacked your bags and settled in, get out and discover the incredible things Middlesboro has on offer. Bell County Historical Society Museum is a popular attraction to add to your must-do list.

Find Hotels with Connecting Rooms in Middlesboro, KY

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