Middlesboro Vacation Rentals : Short-Term Rentals for 2025

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Vacation Rentals in Middlesboro

"The house have space for everyone the kitchens have a lots things to use."

"We really liked the location of this home and the views were beautiful! There were plenty of amenities to meet our needs."

"Enjoyed the view and the property"

"Great experience- accurate listing that ensured space for all!"

"We had a wonderful time. The place had everything we needed, was clean, and provided the perfect setting for our family vacation. "

Smart TV, fireplace, DVD player, foosball

"It was great! "

"So perfect place"

"Had a great stay! Peaceful, cozy cabin in the woods. Since this home is not on the water, providing a boat slip at the marina was perfect. Would stay again!"

"Host was amazing with their information and house had everything we needed!"

"Awesome house!"

"Excellent location and great place to stay. "

"Love the place super relaxing "

"Loved the lake and the view."

"Five days of peace, quiet, birds signing and great views of the lake."

"We have been renting houseboats for years on Norris Lake, however this was our first experience, staying on a houseboat that had to remain at the dock. Honestly, we were a little apprehensive about remaining dock side but ended up, enjoying being dockside more than when we are anchored somewhere on the lake. The staff at Norris Landing was so friendly and helpful. They immediately responded to and resolved any requests, questions, or issues that we had during our stay. Compared to being...

"The weather was chilly but overall we had a great stay and it was a great property"

"Wonderful play to stay."

"We really enjoyed our stay! The property was beautiful!"

"Great property for families and friends to gather. Lots to do and everything you need for a comfortable stay!"

"Would definitely stay at Derrick’s floating cabin again, great location and hospitality! "

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Top Middlesboro Hotel Reviews

9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock

10/10 Excellent

"Great place. Large, clean, and excellent water access. "

LAKE DAZE--Lakefront/No Wake/9br/12ba/Private Dock/Hot Tub/Sleeps 32

10/10 Excellent

"Our family of 25, ranging in age from 1 to 60, spent 7 nights at Lake Daze and could not have asked for a better experience. The home was spacious enough for all of us to be under one roof while still allowing everyone to have their own space when needed.From early morning coffee with a view to late-night laughter around the table, Lake Daze gave us the perfect backdrop to share old family stories and create new ones. The property was clean, well-stocked, and thoughtfully set up for large groups—everything from the kitchen essentials to the gathering spaces made our stay comfortable and stress-free.The location made it easy to enjoy both relaxing downtime and fun family activities, and the owners clearly take pride in making sure guests feel welcome.If you’re looking for a place to bring the whole family together, Lake Daze is it. We left with full hearts, a lot of laughs, and memories we’ll treasure forever. We can’t wait to come back!"

9Bed/9Bath Private Dock Quiet Cove Near Marinas

10/10 Excellent

"We stayed at Southern Comfort 1 for our annual family get together. The house was perfect for our 3 generations of adult couples and singles. The house is three levels, each level with bedrooms, a common area, and a deck overlooking the lake. Two frigs on the top level frig and commercial ice maker on the lower level worked great for a large groups food and drink needs. 3 tables on the top level worked perfect for group meals, games, and cards. Bedrooms were spacious and well appointed. AC worked well; humidity was oppressive the week we were there. Lake houses take a beating but this one was in pretty good shape. Dock worked well for swimming and hanging out, plenty of chairs on the top level for those hanging out. We brought a 26’ speedboat and had plenty of room in the slip. Local ramp 2 blocks away was a plus; avoided a 20 min drive and 25 launch fee at closest marina. Boat trailer parking was challenging but appears ok to leave on green space adjacent to paved roads if lot is full. Cannot leave the vehicle attached to the trailer though, must park in separate designated area. Driveway is steep but manageable for all of our (older) crew. DO NOT try to bring a boat or trailer down the drive. Plenty of room to park our 6 vehicles. Marybeth was extremely responsive and helpful, one of the best hosts we’ve had. Highly recommend and we will be back in the future. "

Find out more about Middlesboro

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, cottages, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlesboro vacation 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 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.

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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?

Waker's Paradise: Lakefront,9br/8.5ba, Private Dock,Hot Tub,Gameroom,Sleeps 32: This vacation home rental near Middlesboro is located on a lake and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with an arcade game room and a hot tub.

How many vacation rentals are there in Middlesboro?

With 4 Expedia vacation rentals, you're sure to find just the right place for your Middlesboro stay.

What’s there to see and do in Middlesboro?

Cumberland Gap National Historical Park and Kentucky Ridge State Forest are a couple of scenic spots to enjoy the outdoors, whereas Bell County Historical Society Museum is one of the cultural attractions. While here, Middlesboro Country Club and Middlesboro Mall 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.

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Middlesboro Vacation Rentals

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Vacation Rentals in Middlesboro

Family Affair, room 4 30, 15 Beds, 2 FULL Kitchens!!! Huge dock w 2 boat slips

Family Affair, room 4 30, 15 Beds, 2 FULL Kitchens!!! Huge dock w 2 boat slips

Dog-friendly waterfront home with a firepit, grill, deck, board games, & dock

Dog-friendly waterfront home with a firepit, grill, deck, board games, & dock

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

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

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

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

Be the family hero - The Great Escape is Waterfrnt, 9 bdrms, with water slide

Be the family hero - The Great Escape is Waterfrnt, 9 bdrms, with water slide

9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock

9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock

Book your fall retreat today!

Book your fall retreat today!

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

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

Lakefront House at Summer Breeze w/ Private Dock w/ Kayaks

Lakefront House at Summer Breeze w/ Private Dock w/ Kayaks

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

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

Lakefront home at Tumbling Run Estates w/ Kayaks

Lakefront home at Tumbling Run Estates w/ Kayaks

LAKE DAZE--Lakefront/No Wake/9br/12ba/Private Dock/Hot Tub/Sleeps 32

LAKE DAZE--Lakefront/No Wake/9br/12ba/Private Dock/Hot Tub/Sleeps 32

Treasure Cove, Waterfront, 9 Bed/9 Bath, Double Decker Dock, arcade games

Treasure Cove, Waterfront, 9 Bed/9 Bath, Double Decker Dock, arcade games

Beautiful lakefront house with full kitchen, private dock, & hot tub

Beautiful lakefront house with full kitchen, private dock, & hot tub

Houseboat Retreat on Norris Lake

Houseboat Retreat on Norris Lake

9Bed/9Bath Private Dock Quiet Cove Near Marinas

9Bed/9Bath Private Dock Quiet Cove Near Marinas

Rock of Ages: 2 Covered Slips, dble decker dock w/slide in deep water quiet cove

Rock of Ages: 2 Covered Slips, dble decker dock w/slide in deep water quiet cove

Book now for Summer! We still have some prime dates available.

Book now for Summer! We still have some prime dates available.

American Spirit --August 23-29 OPEN with 4 night minimum! Gentle Slope to Water

American Spirit --August 23-29 OPEN with 4 night minimum! Gentle Slope to Water

Cozy floating home, AC on Norris Lake at Straight Creek Marina

Cozy floating home, AC on Norris Lake at Straight Creek Marina

Top Middlesboro Hotel Reviews

9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock

Find out more about Middlesboro

Find out more about Middlesboro

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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Frequently asked questions