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Top Holiday Rentals in Middlesboro

4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,

10.0 out of 10, Exceptional, (7)
"Perfect! Owner was awesome and incredibly responsive. The house was immaculate and ideal for us. Wish we could have enjoyed the fire pit too but we were able to stay high and dry and cozy in the house and avoid the torrential downpours. There is even a nice covered area to get to the carport from the house. Neat historical home close to everything and we were honored to be the first VRBO customer. Thank you for a great experience. We will be back!"
The price is £159
includes taxes & fees
30 Jun - 1 Jul
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,

Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

10.0 out of 10, Exceptional, (3)
"We enjoyed our stay. "
The price is £290
includes taxes & fees
1 Jul - 2 Jul
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

A beautiful colonial house with breathtaking views of the Cumberland Gap Mnts!

8.8 out of 10, Excellent, (25)
"Stayed for LMU graduation. Great location and great property, very accommodating hosts. Thank you!"
The price is £453
includes taxes & fees
1 Jul - 2 Jul
A beautiful colonial house with breathtaking views of the Cumberland Gap Mnts!

Harrogate Home Mountain View’s Dog Friendly

10.0 out of 10, Exceptional, (17)
"The entire stay was great. The house was nice and cozy, the beds were comfortable and the showers were great. Overall a very comfortable stay. Great hosts."
The price is £234
includes taxes & fees
30 Jun - 1 Jul
Harrogate Home Mountain View’s Dog Friendly

Charming 3-bedroom house with WiFi, AC in Pineville Kentucky

The price is £203
includes taxes & fees
29 Jun - 30 Jun
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky

1928 Home in the heart of Cumberland Gap

9.8 out of 10, Exceptional, (85)
"Nice spot that is conveniently located in Cumberland Gap. Highly recommend!!!"
The price is £168
includes taxes & fees
6 Jul - 7 Jul
1928 Home in the heart of Cumberland Gap

3-Bedroom Cottage, Peaceful setting, Close to Parks, 2 min. from Bell Theatre

4.0 out of 10, (2)
"The inside photos are somewhat representative of the interior. This is not a “peaceful” location. There were rowdy teens and basketball games very late. Also, you are literally right beside the highway so expect traffic noise. I could deal with all of this, but the smell. I have never left an accommodation nor have I ever left a negative review. However, I must warn others that the smell of tobacco smoke in this place was unlike anything I’ve ever experienced. I went and bought a candle hoping...
The price is £178
includes taxes & fees
27 Jul - 28 Jul
3-Bedroom Cottage, Peaceful setting, Close to Parks, 2 min. from Bell Theatre

Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville

10.0 out of 10, Exceptional, (1)
"Well cared for property with nice upgrades! Perfect for our stay, everything we needed, and accommodating. "
The price is £163
includes taxes & fees
28 Jun - 29 Jun
Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville

Pine Mountain Inn - Minutes from the Laurel Cove and Bell Theatre music venues!

10.0 out of 10, Exceptional, (2)
"Perfect for our event! Very laid back atmosphere. "
The price is £464
includes taxes & fees
1 Jul - 2 Jul
Pine Mountain Inn - Minutes from the Laurel Cove and Bell Theatre music venues!

The House on Park Avenue

3.5 star property
The price is £291
includes taxes & fees
9 Jul - 10 Jul
The House on Park Avenue

Indoor Hot Tub Mountain Top/Retreat 5 mins. to Norris Lake, AC, Wi-Fi and more

10.0 out of 10, Exceptional, (1)
"Absolutely beautiful place. Unbelievable! Will Absolutely be back.Mario and Andrea were fantastic! Can't wait to come back!!"
The price is £293
includes taxes & fees
7 Jul - 8 Jul
Indoor Hot Tub Mountain Top/Retreat 5 mins. to Norris Lake, AC, Wi-Fi and more

Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina

9.2 out of 10, Wonderful, (15)
"Easy to find. Beds were comfortable. Great view of the mountains..."
The price is £134
includes taxes & fees
24 Jul - 25 Jul
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina

Be the family hero - The Great Escape is Waterfrnt, 9 bdrms, with water slide

9.6 out of 10, Exceptional, (70)
"We had a wonderful time. The place had everything we needed, was clean, and provided the perfect setting for our family vacation. "
Be the family hero - The Great Escape is Waterfrnt, 9 bdrms, with water slide
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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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?

Fabulous view, walking distance from Flat Hollow Marina : This holiday home rental outside of Middlesboro is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Middlesboro?

With 5 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?

Cumberland Gap National Historical Park and Kentucky Ridge State Forest are a couple of scenic spots to enjoy the outdoors, whereas Bell County Historical Society Museum is one of the cultural attractions. While here, Middlesboro Mall and Middlesboro Country Club 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.