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Middlesboro Holiday Rentals

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Holiday Rentals in Middlesboro

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

9.8 out of 10, Exceptional, (108)
"It was great! "
9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock

Family Affair, room 4 30, 15 Beds, 2 FULL Kitchens!!! Huge dock w 2 boat slips

10.0 out of 10, Exceptional, (90)
"The home was great and we had plenty of room for 15 of us. The lake was great and the boat dock. Everyone loved the space, pool table and games. My only issue for me and my husband was, we are both 65 and the stairs gave us a challenge, but we did it. The owners were amazing and very accommodating. We really enjoyed the home and our stay. "
Family Affair, room 4 30, 15 Beds, 2 FULL Kitchens!!! Huge dock w 2 boat slips

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

9.8 out of 10, Exceptional, (69)
"We loved the property! We all had a great time! Thank you!"
LAKE DAZE--Lakefront/No Wake/9br/12ba/Private Dock/Hot Tub/Sleeps 32

Forget Me Not Haven – 6BR Lakefront Home for Unforgettable Family Memories

Forget Me Not Haven – 6BR Lakefront Home for Unforgettable Family Memories

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

8.2 out of 10, Very good, (17)
"Cozy and comfortable. I loved having 2 slips available for my boat and jet sky. I also liked the privacy and view to the lake."
Dog-friendly waterfront home with a firepit, grill, deck, board games, & dock

Slip-Away into Isolation & Relaxation w/ Covered Dock & Hot Tub.

9.4 out of 10, Exceptional, (9)
"The house was clean and as stated in the listing. Hank was very quick to respond. Good location close to Powell valley Marina. "
Slip-Away into Isolation & Relaxation w/ Covered Dock & Hot Tub.

Book your fall retreat today!

10.0 out of 10, Exceptional, (51)
"So perfect place"
Book your fall retreat today!

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

9.8 out of 10, Exceptional, (49)
"We stayed at this property with 21 family members for a week. The house was absolutely beautiful and the dock was amazing! The property manager was amazing to communicate with. Definitely a great vacation!!!"
Waker's Paradise: Lakefront,9br/8.5ba, Private Dock,Hot Tub,Gameroom,Sleeps 32

9Bed/9Bath Private Dock Quiet Cove Near Marinas

9.8 out of 10, Exceptional, (185)
"Beautiful house! Everything exceptional except being on a hill with lots of steps! "
9Bed/9Bath Private Dock Quiet Cove Near Marinas

Mountain Lake Retreat w/ Concrete Walkway w/ Kayaks

9.6 out of 10, Exceptional, (35)
"Everything was great. "
Mountain Lake Retreat w/ Concrete Walkway w/ Kayaks

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

10.0 out of 10, Exceptional, (47)
"The house and location was perfect, would definitely stay here again. Host was very responsive with any questions."
Waterfront home with game room, theater, deck, dock & fireplace

Beautiful lakefront house with full kitchen, private dock, & hot tub

9.8 out of 10, Exceptional, (87)
"Our family had a wonderful stay at this awesome lake house! Awesome views and would definitely come back! Thanks for sharing your home with our family!"
Beautiful lakefront house with full kitchen, private dock, & hot tub

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

9.8 out of 10, Exceptional, (49)
"Had an absolute blast at this house. It was great and the hosts were super responsive"
Beautiful Norris Lake Front A-Frame with Private Dock in Speedwell, TN

Treasure Cove, Waterfront, 9 Bed/9 Bath, Double Decker Dock, arcade games

9.8 out of 10, Exceptional, (46)
"We had a great stay here! Everyone loved having their own bathrooms and the house had everything we needed! "
Treasure Cove, Waterfront, 9 Bed/9 Bath, Double Decker Dock, arcade games

Wakes N Shades-Brand New. Private Dock. Hot Tub. 9 Bed/12 Bath.Theater Room

9.6 out of 10, Exceptional, (17)
"We had a great time! The house was perfect with plenty of room for everyone and the kitchen was well stocked for all our cooking needs. We loved the upper deck on the dock! "
Wakes N Shades-Brand New. Private Dock. Hot Tub. 9 Bed/12 Bath.Theater Room

Lakefront Paradise Island

9.6 out of 10, Exceptional, (9)
"This is an ideal lakefront property and well taken care of. We had a great time!"
Lakefront Paradise Island

American Freedom; Theater Rm! Enjoy the Fall Colors! Flexible Chk-in & out times

9.8 out of 10, Exceptional, (10)
"The house was much more then we expected. Clean, very equipped kitchen, easy access to the lake. Going back next year!!!! Need a great house for large family or alot of friends this is the house. "
American Freedom; Theater Rm! Enjoy the Fall Colors! Flexible Chk-in & out times

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

9.6 out of 10, Exceptional, (17)
"Loved the property, everything you need for a nice family lake vacation."
Dog-friendly lakefront house with hot tub, central AC, & mountain view

Lakefront home at Tumbling Run Estates w/ Kayaks

9.6 out of 10, Exceptional, (19)
"Excellent location and great place to stay. "
Lakefront home at Tumbling Run Estates w/ Kayaks

Lakefront w/ Private Dock, 7 BR, Free Kayaks, Firepit, Hot Tub

9.6 out of 10, Exceptional, (86)
"A little tired but appropriate for the money. It had everything we needed. I’d rent it again. "
Lakefront w/ Private Dock, 7 BR, Free Kayaks, Firepit, Hot Tub
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

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, 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?

Beautiful Norris Lake Front A-Frame with Private Dock in Speedwell, TN: This holiday home rental outside of Middlesboro is located on a lake, and has a balcony, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, 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?

Cultural attractions include Bell County Historical Society Museum, whereas Kentucky Ridge State Forest is a spot to enjoy nature. While here, Middlesboro Country Club 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.