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Middlesboro Vacation Rentals

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Vacation Rentals in Middlesboro

Fridge, microwave, oven, stovetop
Lakefront Cottage on Norris Lake
10.0 out of 10, Exceptional, (2)
"Beautiful cottage on the Lake. "
Lakefront Cottage on Norris Lake
Property grounds
Lakefront House at Summer Breeze w/ Private Dock w/ Kayaks
10.0 out of 10, Exceptional, (11)
"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
Exterior
Book Fall 2024 or 2025 thru Sept! Private dock w/Slide in Cove. Firepit. HotTub
9.6 out of 10, Exceptional, (87)
"Property was as advertised! The hosts were very communicative. Everything worked out great! The dock is a little bit of a ride on the provided golf cart! But well worth it."
Book Fall 2024 or 2025 thru Sept! Private dock w/Slide in Cove. Firepit. HotTub
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Property grounds
"Our Happy Place", Floating Home, Sleeps 10; 4 bed/1.5 bath
10.0 out of 10, Exceptional, (3)
"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
Property grounds
Lakefront home with private dock, hot tub & pool table
9.4 out of 10, Exceptional, (30)
"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
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
May 28 - May 29
1928 Home in the heart of Cumberland Gap
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 $282
$727 total
includes taxes & fees
Jun 23 - Jun 24
Dog-friendly lake home with private floating dock - jetted tub, firepit, & decks
Property grounds
Lake Front 2-Bedroom Home W/ Privacy! Beautiful Views & Numerous Amenities...
9.8 out of 10, Exceptional, (136)
"We had a wonderful stay at this property. The view from the patio was beautiful. The home was clean and comfortable. We would definitely stay here again when in the area."
Lake Front 2-Bedroom Home W/ Privacy! Beautiful Views & Numerous Amenities...
Property grounds
Lakefront w/ Private Dock, 7 BR, Free Kayaks, Firepit, Hot Tub
9.8 out of 10, Exceptional, (71)
"For our first family getaway, this was a homerun! The owners were very helpful. The space nice and clean. It was every thing we expected."
Lakefront w/ Private Dock, 7 BR, Free Kayaks, Firepit, Hot Tub
View from property
Lakefront home with private dock and boat launch - dog-friendly & central AC
9.6 out of 10, Exceptional, (21)
"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
Exterior
Dog-friendly lakefront house with hot tub, central AC, & mountain view
10.0 out of 10, Exceptional, (5)
"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
Property grounds
Beautiful lakefront house with full kitchen, private dock, & hot tub
9.8 out of 10, Exceptional, (61)
"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
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
Terrace/patio
Fabulous view, walking distance from Flat Hollow Marina
10.0 out of 10, Exceptional, (2)
"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
Exterior
Waterfront home with game room, theater, deck, dock & fireplace
9.8 out of 10, Exceptional, (19)
"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
Aerial view
Cozy Cottage on Norris Lake
Cozy Cottage on Norris Lake
Exterior
New! LakeFront 7 bedroom Cottage. Private Cove, no Steps to Water, golf cart!
10.0 out of 10, Exceptional, (10)
"Beautiful, well thought out home and property."
New! LakeFront 7 bedroom Cottage. Private Cove, no Steps to Water, golf cart!
Fridge, microwave, oven, stovetop
Brand New Lake House on Norris Lake ~ Includes Paddle Boards and Kayaks!
10.0 out of 10, Exceptional, (66)
"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!
Fridge, microwave, oven, stovetop
Waterfront retreat w/deck, wood fireplace, gas grill, lake views, gas grill, W/D
8.6 out of 10, Excellent, (15)
"House was nice and clean had no complaints would stay here again."
The price is $180
$556 total
includes taxes & fees
May 31 - Jun 1
Waterfront retreat w/deck, wood fireplace, gas grill, lake views, gas grill, W/D
Property grounds
Lake Loop Retreat w/Movie Theater & Private Dock
Lake Loop Retreat w/Movie Theater & Private 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

Exterior
Sleep Inn & Suites
2.5 star property
9.2 out of 10, Wonderful, (565)
"Great place to stay when traveling on our motorcycle "
The price is $108
$119 total
includes taxes & fees
Jun 16 - Jun 17
Sleep Inn & Suites
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, (319)
"The staff was very friendly and helpful. The room was very clean. Although the property appears a little run-down on the outside, everything on the inside was very nice. "
The price is $91
$101 total
includes taxes & fees
Jun 16 - Jun 17
Econo Lodge Middlesboro
Exterior
Holiday Inn Express Williamsburg, an IHG Hotel
2.5 star property
9.0 out of 10, Wonderful, (786)
"."
The price is $123
$139 total
includes taxes & fees
Jun 2 - Jun 3
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 $180 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

Sleep Inn & Suites

Sleep Inn & Suites

5/5 Excellent
"Great place to stay when traveling on our motorcycle "
A verified traveler stayed at Sleep Inn & Suites
Posted 23 hours ago
Sleep Inn & Suites