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Middlesboro Vacation Rentals

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Vacation Rentals in Middlesboro

Lakefront Cottage on Norris Lake
Fridge, microwave, oven, stovetop
Lakefront Cottage on Norris Lake
9.4 out of 10, Exceptional, (3)
"Beautiful cottage on the Lake. "
Lakefront Cottage on Norris Lake
New! LakeFront 7 bedroom Cottage. Private Cove, no Steps to Water, golf cart!
Exterior
New! LakeFront 7 bedroom Cottage. Private Cove, no Steps to Water, golf cart!
9.8 out of 10, Exceptional, (12)
"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
Fridge, microwave, oven, stovetop
Dog-friendly lake home with private floating dock - jetted tub, firepit, & decks
6.0 out of 10, (6)
"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 $165
$566 total
includes taxes & fees
Jun 17 - Jun 18
Dog-friendly lake home with private floating dock - jetted tub, firepit, & decks
"Our Happy Place", Floating Home, Sleeps 10; 4 bed/1.5 bath
Property grounds
"Our Happy Place", Floating Home, Sleeps 10; 4 bed/1.5 bath
10.0 out of 10, Exceptional, (4)
"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
View from property
Lakefront home with private dock and boat launch - dog-friendly & central AC
9.6 out of 10, Exceptional, (23)
"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
Property grounds
Beautiful lakefront house with full kitchen, private dock, & hot tub
9.8 out of 10, Exceptional, (63)
"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...
Property grounds
Lake Front 2-Bedroom Home W/ Privacy! Beautiful Views & Numerous Amenities...
9.8 out of 10, Exceptional, (137)
"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
Exterior
Waterfront home with game room, theater, deck, dock & fireplace
9.8 out of 10, Exceptional, (20)
"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
Exterior
1928 Home in the heart of Cumberland Gap
9.8 out of 10, Exceptional, (66)
"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 $200
$254 total
includes taxes & fees
Jun 19 - Jun 20
1928 Home in the heart of Cumberland Gap
Dog-friendly lakefront house with hot tub, central AC, & mountain view
Exterior
Dog-friendly lakefront house with hot tub, central AC, & mountain view
9.8 out of 10, Exceptional, (6)
"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
Property grounds
Lakefront w/ Private Dock, 7 BR, Free Kayaks, Firepit, Hot Tub
9.6 out of 10, Exceptional, (72)
"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
Exterior
Book Fall 2024 or 2025 thru Sept! Private dock w/Slide in Cove. Firepit. HotTub
9.6 out of 10, Exceptional, (90)
"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
Fridge, microwave, oven, stovetop
Lakefront home - dog-friendly, private dock, two fireplaces, and central AC
9.6 out of 10, Exceptional, (14)
"Clean and roomy."
Lakefront home - dog-friendly, private dock, two fireplaces, and central AC
Lakein' It Easy With Private Dock
Property grounds
Lakein' It Easy With Private Dock
10.0 out of 10, Exceptional, (24)
"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
Property grounds
Lakefront home with private dock, hot tub & pool table
9.6 out of 10, Exceptional, (31)
"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
Fridge, microwave, oven, stovetop
2-story lakefront rustic cabin w/pool table, private hot tub, gas fireplace, A/C
9.6 out of 10, Exceptional, (24)
"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!
Property grounds
Quaint, Rustic Lakefront Log Cabin on Wooded Lot at Norris Lake ,Private Dock!
9.6 out of 10, Exceptional, (51)
"Wonderful time the cabin was perfect for my husband and I"
The price is $195
$412 total
includes taxes & fees
Jun 17 - Jun 18
Quaint, Rustic Lakefront Log Cabin on Wooded Lot at Norris Lake ,Private Dock!
Fabulous view, walking distance from Flat Hollow Marina
Terrace/patio
Fabulous view, walking distance from Flat Hollow Marina
10.0 out of 10, Exceptional, (3)
"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
Property grounds
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
Fridge, microwave, oven, stovetop
Dog-friendly waterfront home with a firepit, grill, deck, board games, & dock
9.0 out of 10, Wonderful, (2)
Dog-friendly waterfront home with a firepit, grill, deck, board games, & dock
Don't see what you're looking for?
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
Exterior
Sleep Inn & Suites
2.5 star property
9.2 out of 10, Wonderful, (570)
"The king size bed was very comfortable as were the 5 pillows. The shower was great as well. "
The price is $116
$128 total
includes taxes & fees
Jul 1 - Jul 2
Sleep Inn & Suites
Econo Lodge Middlesboro
Standard Room, 2 Double Beds, Non Smoking | Laptop workspace, blackout drapes, iron/ironing board, free WiFi
Econo Lodge Middlesboro
2.0 star property
6.8 out of 10, (322)
"Great stay staff was awesome!!! Room could use updating but was clean and ok but the staff was GREAT"
The price is $97
$108 total
includes taxes & fees
Jul 1 - Jul 2
Econo Lodge Middlesboro
Holiday Inn Express Williamsburg, an IHG Hotel
Exterior
Holiday Inn Express Williamsburg, an IHG Hotel
2.5 star property
9.0 out of 10, Wonderful, (797)
"Relaxing trip"
The price is $123
$139 total
includes taxes & fees
Jun 23 - Jun 24
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.

Everything you need to know about Middlesboro vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middlesboro vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middlesboro vacation 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 low season months. For more hustle and bustle, you may prefer to visit Middlesboro in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $165 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middlesboro rentals

At Expedia, we put the best Middlesboro vacation 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 vacation.

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 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

New! LakeFront 7 bedroom Cottage. Private Cove, no Steps to Water, golf cart!

New! LakeFront 7 bedroom Cottage. Private Cove, no Steps to Water, golf cart!

5/5 Excellent
Family vacation
"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!!!"
A verified traveler stayed at New! LakeFront 7 bedroom Cottage. Private Cove, no Steps to Water, golf cart!
Posted 2 days ago
New! LakeFront 7 bedroom Cottage. Private Cove, no Steps to Water, golf cart!