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Holiday Rentals in Middlesboro

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Our top choices for Middlesboro holiday rentals

10.0 out of 10, Exceptional, (23)
"Very nice and extra clean great time"
United States
Johnny C.
The price is €202
includes taxes & fees
4 Jan - 5 Jan
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
3-bedroom home away from home in Middesboro. A family friendly environment.
9.2 out of 10, Wonderful, (5)
"We enjoyed our stay. "
United States
Emily S.
The price is €323
includes taxes & fees
4 Jan - 5 Jan
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
10.0 out of 10, Exceptional, (1)
"Clean"
United States
Phineas S.
The price is €510
includes taxes & fees
24 Jan - 25 Jan
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
The price is €263
includes taxes & fees
25 Jan - 26 Jan
Welcoming 3-bedroom house with AC in charming Middlesboro
2.0 star property
The price is €112
includes taxes & fees
5 Jan - 6 Jan
Modern 20’ Travel Trailer with bunks and a queen bed

Camping in Speedwell

RV/Camper Sites. No Electric
2.0 star property
The price is €64
includes taxes & fees
5 Jan - 6 Jan
RV/Camper Sites. No Electric
10.0 out of 10, Exceptional, (4)
"Everything was clean and felt like home.host was really nice and I will definitely be staying again."
United States
Nicholas H.
The price is €141
includes taxes & fees
4 Jan - 5 Jan
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
9.2 out of 10, Wonderful, (42)
"Great location. Easy walk to town and close to hiking areas. Highly recommend. "
United States
Linda O.
The price is €185
includes taxes & fees
8 Jan - 9 Jan
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cabin in Speedwell

One Bedroom Rustic Cabin
2.0 star property
The price is €78
includes taxes & fees
4 Jan - 5 Jan
One Bedroom Rustic Cabin

Apartment in Harlan

Beautiful Loft in the Woods
10.0 out of 10, Exceptional, (3)
"Beautiful setting. Incredible space well laid out. Owner was very engaging. "
United States
Fred
The price is €203
includes taxes & fees
4 Jan - 5 Jan
Beautiful Loft in the Woods
3.0 star property
The price is €261
includes taxes & fees
4 Jan - 5 Jan
Peaceful & Private! Pet-friendly Williamsburg Home
2.0 star property
10.0 out of 10, Exceptional, (2)
"The cabin was clean, cozy, and overall amazing! "
United States
Fannie
The price is €180
includes taxes & fees
4 Jan - 5 Jan
The Highlands Cabin Retreat at Norris Lake
9.4 out of 10, Exceptional, (22)
"The hosts was great to communicate with. Everything was so smooth. There is a Dollar General down the road if you need quick groceries. House was clean and in good shape. We loved the creek behind the house. "
United States
Autumn
The price is €227
includes taxes & fees
4 Jan - 5 Jan
Calm Country Oasis - Creek, ATV Trls & Norris Lake
9.6 out of 10, Exceptional, (25)
"This place was just as described and perfect for our stay!"
United States
Melissa M.
The price is €174
includes taxes & fees
4 Jan - 5 Jan
Luxury Brooklyn St APT - Near LMU & Nat’l Park
9.4 out of 10, Exceptional, (19)
"It was exceptional "
United States
Dennis W.
The price is €122
includes taxes & fees
5 Jan - 6 Jan
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
The price is €417
includes taxes & fees
4 Jan - 5 Jan
Waterfront Retreat, Sleeps 12・Fireplace・Grill・Dock
10.0 out of 10, Exceptional, (5)
"This was definitely the most romantic VRBO we’ve stayed at!!! Very clean, and the view from all of the balconies was incredible!!! "
United States
Stan N.
The price is €248
includes taxes & fees
5 Jan - 6 Jan
Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's
2.0 star property
The price is €262
includes taxes & fees
4 Jan - 5 Jan
Peaceful & Private! Pet-Friendly Williamsburg Home
10.0 out of 10, Exceptional, (22)
"Great location with friendly neighbors!"
United States
Evan C.
The price is €261
includes taxes & fees
4 Jan - 5 Jan
Harrogate Home Mountain View’s Dog Friendly
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.
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Top Middlesboro Hotel Reviews

Find out more about Middlesboro

Everything you need to know about Middlesboro holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middlesboro holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middlesboro holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Middlesboro holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middlesboro. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middlesboro holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlesboro holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middlesboro rentals

At Expedia, we put the best Middlesboro holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Middlesboro rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middlesboro holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middlesboro. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Middlesboro?

Yes, there are holiday rentals close to the most popular sights in Middlesboro, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the mountain landscape in Middlesboro. Make sure you have time to check out the churches while you're in the area.

What are some of the best holiday rentals that Middlesboro has to offer?

8BR Lakefront Lux Retreat: Private Dock, Sleeps 28: This holiday home rental outside of Middlesboro is located on a lake, and has a fireplace, an arcade/games room and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals are there in Middlesboro?

With 6 Expedia holiday rentals, you're guaranteed to find just the right place for your Middlesboro stay.

What’s there to see and do in Middlesboro?

Cultural attractions include Bell County Historical Society Museum, whereas Kentucky Ridge State Forest is a spot to enjoy nature. While here, Cumberland Gap National Historical Park and Middlesboro Mall are other places worth a visit.

What’s a holiday rental in Middlesboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middlesboro. Holiday rentals feature amenities such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for families.