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Middlesboro Vacation Rentals

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Vacation 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
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 CA $273
CA $347 total
includes taxes & fees
Jun 16 - Jun 17
1928 Home in the heart of Cumberland Gap
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 CA $300
CA $875 total
includes taxes & fees
Jun 23 - Jun 24
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, 3 reviews
"The best hosts ever!! Jack was so responsive and accomodating. The space is so clean, comfortable, spacious and ready to enjoy the lake!! I highly recommend this location for your next Norris Lake vacation!!"
"Our Happy Place", Floating Home, Sleeps 10; 4 bed/1.5 bath
Book Fall 2024 or 2025 thru Sept! Private dock w/Slide in Cove. Firepit. HotTub
9.6 out of 10, Exceptional, 89 reviews
"All was great, one bed had wrong linens and the king down to lake is very steep."
Book Fall 2024 or 2025 thru Sept! Private dock w/Slide in Cove. Firepit. HotTub
Lakefront home with private dock and boat launch - dog-friendly & central AC
9.6 out of 10, Exceptional, 21 reviews
"We absolutely loved our stay in the dawg pound vacation house on Norris lake. The house was so cozy and inviting and had everything we needed for an enjoyable stay. We would recommend this property to everyone! It’s worth the price! We will definitely be staying there again!!"
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, 62 reviews
"Our stay was wonderful. The home is beautiful and immaculately kept with all the utensils and towels you could need. Only complaints are the oven didn’t seem to regulate the temperature like it should. The upstairs also got exceptionally hot while downstairs was cold. The interior of the home feels very dark at night and could benefit from brighter lighting. The exterior was also lacking lights by the hot tub area, which could present a safety concern . All of that said, we would stay here again...
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...
New! LakeFront 7 bedroom Cottage. Private Cove, no Steps to Water, golf cart!
10.0 out of 10, Exceptional, 10 reviews
"Beautiful, well thought out home and property."
New! LakeFront 7 bedroom Cottage. Private Cove, no Steps to Water, golf cart!
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 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
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
Waterfront home with game room, theater, deck, dock & fireplace
9.8 out of 10, Exceptional, 19 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
Lakefront House at Summer Breeze w/ Private Dock w/ Kayaks
10.0 out of 10, Exceptional, 11 reviews
"The house was great fishing was so so. Need to work on the timing of fishing"
Lakefront House at Summer Breeze w/ Private Dock w/ Kayaks
Brand New Lake House on Norris Lake ~ Includes Paddle Boards and Kayaks!
10.0 out of 10, Exceptional, 66 reviews
"Wonderful place to stay! Wonderful accommodations both inside and outside! Well stocked kitchen, comfy beds, clean home, screened in back deck with seating, table, and hot tub. Great working grill and well stocked woodpile for the fire pit. Our family loved fishing off the dock, kayaking, and paddle boarding. The owners were wonderful to work with and we would love to return!"
Brand New Lake House on Norris Lake ~ Includes Paddle Boards and Kayaks!
Lakein' It Easy With Private Dock
10.0 out of 10, Exceptional, 24 reviews
"Very nice place, out of the way..bring food and snacks! Host was very helpful..."
Lakein' It Easy With Private Dock
Lakefront, minimal steps, private dock, quiet cove, sleeps 24, Space for fun!
9.8 out of 10, Exceptional, 163 reviews
"We had a wonderful time at our family reunion. Plenty of room, everything was great. Communication was very good and everything was working and the place was very clean. Would go back again. Great location."
Lakefront, minimal steps, private dock, quiet cove, sleeps 24, Space for fun!
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
Fabulous view, walking distance from Flat Hollow Marina
10.0 out of 10, Exceptional, 2 reviews
"Nice property, great for your dog to run around, grass was long making it hard to find the droppings. The property is convenient to the marina although up a steep hill, there are a couple of sets of stairs to the chalets and another rental that drops you off a few yards from the drive. Plenty of cooking items, pots pans, baking sheets silverware. Master bath is very cozy there is not much room between the corner of the vanity and the edge of the shower to get to the toilet, must be thin to...
Fabulous view, walking distance from Flat Hollow Marina
Lake Loop Retreat w/Movie Theater & Private Dock
Lake Loop Retreat w/Movie Theater & Private 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, 566 reviews
"Great place to stay when traveling on our motorcycle "
The price is CA $148
CA $163 total
includes taxes & fees
Jun 23 - Jun 24
Sleep Inn & Suites
Econo Lodge Middlesboro
2.0 star property
6.8 out of 10, 321 reviews
"Everything was good. Not a great big breakfast but that was okay! I was pleasantly pleased when I walked into our room, it had a clean smell! That made a huge difference for me! "
The price is CA $125
CA $139 total
includes taxes & fees
Jun 23 - Jun 24
Econo Lodge Middlesboro
Holiday Inn Express Williamsburg, an IHG Hotel
2.5 star property
9.0 out of 10, Wonderful, 794 reviews
"Relaxing trip"
The price is CA $167
CA $189 total
includes taxes & fees
Jun 9 - Jun 10
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Middlesboro?

Yes, we offer vacation rentals close to the most popular sights in Middlesboro, or you can choose a secluded option if you'd like a relaxing place to 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's the top vacation rental that Middlesboro has to offer?

Dog-friendly lakefront house with hot tub, central AC, & mountain view: This vacation home rental near Middlesboro is located on a lake and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a spa 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 vacation rental in Middlesboro like?

Vacation rentals are private properties you can stay in for short or long periods in Middlesboro. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for small groups.

Recent reviews of Middlesboro properties
Expedia verified reviews