Photo by Alexis Wyrick

Holiday Rentals in Middlesboro

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Holiday Rentals in Middlesboro

Dog-friendly waterfront home with a firepit, grill, deck, board games, & dock

8.4 out of 10, Very good, (12)
"We really liked the location of this home and the views were beautiful! There were plenty of amenities to meet our needs."
Dog-friendly waterfront home with a firepit, grill, deck, board games, & dock

Fabulous view, walking distance from Flat Hollow Marina

10.0 out of 10, Exceptional, (11)
"Perfect for all our needs, clean, close to the marina."
Fabulous view, walking distance from Flat Hollow Marina

Lakefront home at Tumbling Run Estates w/ Kayaks

9.8 out of 10, Exceptional, (15)
"Awesome house and location Gorgeous, convenient and lots of fun for all ages and big family.gatherings. We also rented a pontoon and it was great too! Planning our next trip! Highly recommend."
Lakefront home at Tumbling Run Estates w/ Kayaks

9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock

9.8 out of 10, Exceptional, (103)
"We went to ride the trails and enjoy the lake life. It was an awesome place. "
9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock

9 bdrm covered dock, firepit and large bar on water, Baltic hot tub, sleeps 26,

10.0 out of 10, Exceptional, (1)
"This place was absolutely incredible! You can tell the owners have put lots of time and thought into making sure the stay is nothing short of amazing. The room themes are just so cool! The house was very clean, spacious, well maintained, and fully equipped with everything you may need. The host was very responsive and had great communication throughout the whole stay. The views of the lake from the house were absolutely stunning! We also rented a pontoon boat from them and the boat was in great...
9 bdrm covered dock, firepit and large bar on water, Baltic hot tub, sleeps 26,

Dog-friendly lake home with private floating dock - jetted tub, firepit, & decks

7.6 out of 10, Good, (17)
"Overall, the cabin was decent. Enjoyed the rustic feel of it. All amenities worked well and there was sufficient room for multiple families. "
Dog-friendly lake home with private floating dock - jetted tub, firepit, & decks

Beautiful Norris Lake Front A-Frame with Private Dock in Speedwell, TN

10.0 out of 10, Exceptional, (43)
"Wonderful vacation"
Beautiful Norris Lake Front A-Frame with Private Dock in Speedwell, TN

What a Life - Norris Lake Front House w/ dock, hot tub and NO-steps to lake

9.4 out of 10, Exceptional, (19)
"Grateful for family thanksgiving"
What a Life - Norris Lake Front House w/ dock, hot tub and NO-steps to lake

Dog-friendly lakefront house with hot tub, central AC, & mountain view

9.6 out of 10, Exceptional, (11)
"Loved the property, everything you need for a nice family lake vacation."
Dog-friendly lakefront house with hot tub, central AC, & mountain view

LAKE DAZE--Lakefront/No Wake/9br/12ba/Private Dock/Hot Tub/Sleeps 32

9.6 out of 10, Exceptional, (63)
"Love the place super relaxing "
LAKE DAZE--Lakefront/No Wake/9br/12ba/Private Dock/Hot Tub/Sleeps 32

Waker's Paradise: Lakefront,9br/8.5ba, Private Dock,Hot Tub,Gameroom,Sleeps 32

9.6 out of 10, Exceptional, (44)
"Great experience- accurate listing that ensured space for all!"
Waker's Paradise: Lakefront,9br/8.5ba, Private Dock,Hot Tub,Gameroom,Sleeps 32

3-Bdrm Home on Large Property at Norris Lake. Boat Slip included & Pet Friendly!

9.0 out of 10, Wonderful, (2)
"The property was well taken care of and clean. The parking situation was a bit tricky because of the steep driveway but manageable. Only issue was the storm door hardware was attached in front of the house door knob and made it difficult to close the door without injuring your hand. That said I would recommend the property. It is very convenient to the marina for fishermen. "
3-Bdrm Home on Large Property at Norris Lake. Boat Slip included & Pet Friendly!

Norris Nook: Lakefront 9br/11ba, Private Dock,Private HotTub,Sleeps 32, Gameroom

10.0 out of 10, Exceptional, (49)
" "
Norris Nook: Lakefront 9br/11ba, Private Dock,Private HotTub,Sleeps 32, Gameroom

Lakefront House at Summer Breeze w/ Private Dock w/ Kayaks

10.0 out of 10, Exceptional, (19)
"Host was amazing with their information and house had everything we needed!"
Lakefront House at Summer Breeze w/ Private Dock w/ Kayaks

Lake Front - Gorgeous views, 6 bedroom/ 6 1/2 baths, 2 refrigerators/dishwashers

10.0 out of 10, Exceptional, (17)
"The home had plenty of space to spread out and easy access to the lake! We had a great time!"
Lake Front - Gorgeous views, 6 bedroom/ 6 1/2 baths, 2 refrigerators/dishwashers

Charming Norris Lake Cabin with views and boat slip @ Marina!

2.0 star property
10.0 out of 10, Exceptional, (8)
"Had a great stay! Peaceful, cozy cabin in the woods. Since this home is not on the water, providing a boat slip at the marina was perfect. Would stay again!"
Charming Norris Lake Cabin with views and boat slip @ Marina!

Waterfront home with game room, theater, deck, dock & fireplace

10.0 out of 10, Exceptional, (41)
"We enjoyed our stay and the kids had fun"
Waterfront home with game room, theater, deck, dock & fireplace

Norris lakefront home with covered boat dock

10.0 out of 10, Exceptional, (60)
"Wonderful place to stay, only thing I would change is bigger towels for use after the shower."
Norris lakefront home with covered boat dock

Lakefront home with private dock and boat launch - dog-friendly & central AC

9.6 out of 10, Exceptional, (34)
"The house is very confortable , you will find everything you need for your vacations."
Lakefront home with private dock and boat launch - dog-friendly & central AC

Lovely dog-friendly cabin overlooking the river w/kids games, Wi-Fi

2.0 star property
9.0 out of 10, Wonderful, (2)
"We spent alot of time on the back deck enjoying the river, the wildlife, and beautiful views. Also walked our inflatable kayak down to the river for a peaceful paddle. The hike down is steep! Inside has everything you need, except bring your own keurig cups! cups"
Lovely dog-friendly cabin overlooking the river w/kids games, Wi-Fi
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.
Save an average of 15% on thousands of hotels when you're signed in

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.