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Middlesboro Holiday Rentals

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Holiday Rentals in Middlesboro

Lakefront Cottage on Norris Lake
9.4 out of 10, Exceptional, 3 reviews
"Beautiful cottage on the Lake. "
Lakefront Cottage on Norris Lake
New! LakeFront 7 bedroom Cottage. Private Cove, no Steps to Water, golf cart!
9.8 out of 10, Exceptional, 12 reviews
"This property does not disappoint at all. It was so accommodating for our entire family. The house was completely stocked with everything we needed. We loved every minute of our stay. The host was super responsive to all of our questions. Highly recommend this property! Our family loves it!! It’s amazing!!!"
New! LakeFront 7 bedroom Cottage. Private Cove, no Steps to Water, golf cart!
Dog-friendly lake home with private floating dock - jetted tub, firepit, & decks
6.0 out of 10, 6 reviews
"Many issues stated in previous reviews are unresolved. Smoke alarms are missing, expired fire extinguisher, poor quality cookware, substandard furniture. The bunk bed in the basement is unusable for two people because it is not sturdy. The gas grill caught on fire because of all the residual grease and the grease tray ended up dropping out of the grill due to its poor condition. The property manager offered to bring us a new grill so hopefully the next guests won’t have this issue. Numerous...
The price is NZ$922
per night
19 Jun - 20 Jun
Dog-friendly lake home with private floating dock - jetted tub, firepit, & decks
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"Our Happy Place", Floating Home, Sleeps 10; 4 bed/1.5 bath
10.0 out of 10, Exceptional, 4 reviews
"The floating boat house is in a wonderful location and has everything you need for a peaceful get away on beautiful Norris lake. The owners do a wonderful job decorating and providing a kitchen with everything you need to prepare meals during your stay. Very clean and comfortable. We rented a pontoon from Straight Creek Marina and they were very nice and accommodating as well. We absolutely loved our time at “Our Happy Place”"
"Our Happy Place", Floating Home, Sleeps 10; 4 bed/1.5 bath
Lakefront home with private dock and boat launch - dog-friendly & central AC
9.6 out of 10, Exceptional, 23 reviews
"The Dawg Pound was great! Very clean and comfortable, the steps to the second level of the house was a little steep, a little hard to access if you have any knee or hip problems. Other than that, it was great!"
Lakefront home with private dock and boat launch - dog-friendly & central AC
Beautiful lakefront house with full kitchen, private dock, & hot tub
9.8 out of 10, Exceptional, 63 reviews
"The house was beautiful and property was very private, this was the perfect place for a relaxing getaway. Beds were comfortable, they provided plenty of beach towels, kayaks, and firewood (to be replaced if you used some). There are no houses across the lake, so you have an unobstructed view of the lake. Only advice if you're brining young ones is to buy a roll of window screen/mesh to wrap around the front porch rail so that it's childproofed. Overall, this house exceeded expectations and we...
Beautiful lakefront house with full kitchen, private dock, & hot tub
Lake Front 2-Bedroom Home W/ Privacy! Beautiful Views & Numerous Amenities...
9.8 out of 10, Exceptional, 137 reviews
"Great location. The cabin had an amazing view of the lake. Very secluded and just what you need to unwind on vacation. The cabin was equipped with everything we want. Would definitely book this cabin again!"
Lake Front 2-Bedroom Home W/ Privacy! Beautiful Views & Numerous Amenities...
Waterfront home with game room, theater, deck, dock & fireplace
9.8 out of 10, Exceptional, 20 reviews
"We had a marvelous time in this space. It was fun for my friend’s grandkids and the popcorn machine and movie room were a huge blessing on a rainy day!"
Waterfront home with game room, theater, deck, dock & fireplace
1928 Home in the heart of Cumberland Gap
9.8 out of 10, Exceptional, 66 reviews
"This is a great little home in Cumberland Gap. Walking distance to restaurants and a coffee shop. The views from the home are amazing. Be sure to visit The Summit while you are there."
The price is NZ$413
per night
19 Jun - 20 Jun
1928 Home in the heart of Cumberland Gap
Dog-friendly lakefront house with hot tub, central AC, & mountain view
9.8 out of 10, Exceptional, 6 reviews
"Property exactly as pictured. Lots of space and very well equipped. Nice decoration. Good communication for small hiccup. Don’t hesitate to book"
Dog-friendly lakefront house with hot tub, central AC, & mountain view
Lakefront w/ Private Dock, 7 BR, Free Kayaks, Firepit, Hot Tub
9.6 out of 10, Exceptional, 72 reviews
"We had a great time here! Plenty of room for us and our children/grandchildren. Property manager quickly responded to any needs, parking is a bit tricky but we got the hang of it. Definitely would stay there again."
Lakefront w/ Private Dock, 7 BR, Free Kayaks, Firepit, Hot Tub
Book Fall 2024 or 2025 thru Sept! Private dock w/Slide in Cove. Firepit. HotTub
9.6 out of 10, Exceptional, 90 reviews
"Our family vacation included a wide age range of people and everyone had a great time here! Only problems were one squeaky, uncomfortable bed out of the 8 bedrooms. Also, you have to make your own beds upon arrival. Otherwise, plenty of space! 2 refrigerators and dishwashers. The golf cart was a life saver getting to the dock and back. Everything was clean and the property manager/ owners were very responsive! We want to stay there again!"
Book Fall 2024 or 2025 thru Sept! Private dock w/Slide in Cove. Firepit. HotTub
Lakefront home - dog-friendly, private dock, two fireplaces, and central AC
9.6 out of 10, Exceptional, 14 reviews
"Clean and roomy."
Lakefront home - dog-friendly, private dock, two fireplaces, and central AC
Lakein' It Easy With Private Dock
10.0 out of 10, Exceptional, 24 reviews
"This was a nice cabin. A bit big for our family of three but we were looking last minute and wanted to be on the lake. The paddleboat was fun and property has a nice fire pit. Bring fire starters. Will help start the fire pit. Has a propane grill which was convenient. The drive from the main road is very wavy. But our plan was to stay at cabin and enjoy lake entire time so it didnt bother us. We did our grocery shopping ahead of time as the nearest decent grocery store is a 30 min...
Lakein' It Easy With Private Dock
Lakefront home with private dock, hot tub & pool table
9.6 out of 10, Exceptional, 31 reviews
"This was the perfect get away for our family. Loved every moment spent in this beautiful, clean, peaceful Home. Fully stocked with everything we needed. Excellent views, loved the sunrise over the mountains the reflections shinning on the water with the different colors were calming. The pier was nice to fish off of, we all enjoyed fishing and took out some time grilling out on the balcony/patio. Very nice setup for outdoor enjoyment. Beds were comfortable, Plenty of privacy inside this home....
Lakefront home with private dock, hot tub & pool table
2-story lakefront rustic cabin w/pool table, private hot tub, gas fireplace, A/C
9.6 out of 10, Exceptional, 24 reviews
"Relaxing"
2-story lakefront rustic cabin w/pool table, private hot tub, gas fireplace, A/C
Quaint, Rustic Lakefront Log Cabin on Wooded Lot at Norris Lake ,Private Dock!
9.6 out of 10, Exceptional, 51 reviews
"Wonderful time the cabin was perfect for my husband and I"
The price is NZ$670
per night
26 Jun - 27 Jun
Quaint, Rustic Lakefront Log Cabin on Wooded Lot at Norris Lake ,Private Dock!
Fabulous view, walking distance from Flat Hollow Marina
10.0 out of 10, Exceptional, 3 reviews
"Perfect for all our needs, clean, close to the marina."
Fabulous view, walking distance from Flat Hollow Marina
Lake Loop Retreat w/Movie Theater & Private Dock
Lake Loop Retreat w/Movie Theater & Private Dock
Dog-friendly waterfront home with a firepit, grill, deck, board games, & dock
9.0 out of 10, Wonderful, 2 reviews
Dog-friendly waterfront home with a firepit, grill, deck, board games, & dock
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See all available properties in Middlesboro
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.

Other types of properties in Middlesboro you may be interested in

Sleep Inn & Suites
2.5 star property
9.2 out of 10, Wonderful, 573 reviews
"The king size bed was very comfortable as were the 5 pillows. The shower was great as well. "
The price is NZ$200
per night
14 Jul - 15 Jul
Sleep Inn & Suites
Econo Lodge Middlesboro
2.0 star property
6.8 out of 10, 322 reviews
"Great stay staff was awesome!!! Room could use updating but was clean and ok but the staff was GREAT"
The price is NZ$169
per night
14 Jul - 15 Jul
Econo Lodge Middlesboro
Holiday Inn Express Williamsburg, an IHG Hotel
2.5 star property
9.0 out of 10, Wonderful, 803 reviews
"This was the cleanest Hotel I have ever stayed at. Breakfast was excellent the staff was amazing. I highly recommend and if i could give 10 stars I most definitely would. "
The price is NZ$222
per night
7 Jul - 8 Jul
Holiday Inn Express Williamsburg, an IHG Hotel
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Middlesboro holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Middlesboro. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Middlesboro. Seeing all the best attractions is bound to make you fall in love with Middlesboro. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Middlesboro short-term rentals, that won’t be hard to do.

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?

Dog-friendly lakefront house with hot tub, central AC, & mountain view: This holiday home rental outside of Middlesboro is located on a lake, and has a fireplace, a patio 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. You can relax into your holiday with 1 hot tub and a selection of books.

What’s there to see and do in Middlesboro?

Enjoy the area's cultural attractions such as Bell County Historical Society Museum, or get outdoors into nature at a spot like Cumberland Gap National Historical Park. 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.

Recent reviews of Middlesboro properties
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