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Holiday Rentals in Middlesboro

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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)
"we enjoyed this home, house was clean and everything was in good working order. The boat dock was great for swimming and the boat slip was great to have for our boat.we would have liked for there to be a slide for the kids to enjoy. overall this home accommodated our family very well"
Family Affair, room 4 30, 15 Beds, 2 FULL Kitchens!!! Huge dock w 2 boat slips

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.

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

Book your fall retreat today!

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

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

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

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

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

9.8 out of 10, Exceptional, (50)
"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

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

2.0 star property
9.4 out of 10, Exceptional, (16)
"Great place to unwind with your spouse or family "
Charming Norris Lake Cabin with views and boat slip @ Marina!

9Bed/9Bath Private Dock Quiet Cove Near Marinas

9.8 out of 10, Exceptional, (187)
"Location was wonderful! Despite a handful of neighbors, we loved being tucked back in a cove where the water was calm. There was plenty of room for each family member. We enjoyed our daily swims off the dock. "
9Bed/9Bath Private Dock Quiet Cove Near Marinas

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

10.0 out of 10, Exceptional, (5)
"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,

Secluded No Wake Cove - Private Covered Dock-Screened Porch-Kayaks

10.0 out of 10, Exceptional, (43)
"The home is well maintained, with plenty of amenities. The layout is perfect for family and friends. The host was exceptionally responsive to any and all of our questions. We certainly enjoyed our stay here and look forward to staying here again."
Secluded No Wake Cove - Private Covered Dock-Screened Porch-Kayaks

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, (18)
"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

Entertainment in Abundance, Putting Green, Games, Kayaks, No-wake Covered Dock!

8.8 out of 10, Excellent, (11)
"Beautiful home in a great location! The house was well equipped and had lots of games and outdoor activities for the kids to enjoy. "
Entertainment in Abundance, Putting Green, Games, Kayaks, No-wake Covered Dock!

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

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

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

Brand New! Lakefront, minimal steps to water. Large private dock, Chef's kitchen

10.0 out of 10, Exceptional, (16)
"Great beautiful property with incredible dock and deck. Slightly difficult to get to location/find it but otherwise great stay "
Brand New! Lakefront, minimal steps to water. Large private dock, Chef's kitchen
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, 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?

9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock: This holiday home rental outside of Middlesboro is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 9 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

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.