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Middlesboro Vacation Rentals

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Tonight
Aug 7 - Aug 8
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Aug 8 - Aug 9
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Vacation Rentals in Middlesboro

Waker's Paradise: Lakefront,9br/8.5ba, Private Dock,Hot Tub,Gameroom,Sleeps 32
Enjoy cooking and dining in this spacious kitchen with a large island, high ceiling, and dining area.

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

9.8 out of 10, Exceptional, (47)
"Great experience- accurate listing that ensured space for all!"
Waker's Paradise: Lakefront,9br/8.5ba, Private Dock,Hot Tub,Gameroom,Sleeps 32
Cozy floating home, AC on Norris Lake at Straight Creek Marina
Relax in this cabin with a high ceiling, ceiling fan, and comfortable seating area featuring a couch and small table.

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

10.0 out of 10, Exceptional, (1)
"Would definitely stay at Derrick’s floating cabin again, great location and hospitality! "
Cozy floating home, AC on Norris Lake at Straight Creek Marina
Dog-friendly waterfront home with a firepit, grill, deck, board games, & dock
Fully equipped kitchen with stainless steel appliances, including a dishwasher, microwave, and oven, and a convenient black mat at the entrance.

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

8.0 out of 10, Very Good, (16)
"We really liked the location of this home and the views were beautiful! There were plenty of amenities to meet our needs."
Dog-friendly waterfront home with a firepit, grill, deck, board games, & dock
LakeFront 7 bedroom Cottage. Private Cove, no Steps to Water, golf cart!
Stunning two-story home with a symmetrical design, featuring a covered porch and lush green surroundings.

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

10.0 out of 10, Exceptional, (30)
"Enjoyed the view and the property"
LakeFront 7 bedroom Cottage. Private Cove, no Steps to Water, golf cart!
9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock
Relax in this inviting living area with a high ceiling, stone fireplace, and comfortable sofa.

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

9.8 out of 10, Exceptional, (104)
"It was great! "
9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock
Calm Country Oasis - Creek, ATV Trls & Norris Lake
Relax by the fire pit in a serene natural setting surrounded by lush greenery and a small stream.

Calm Country Oasis - Creek, ATV Trls & Norris Lake

9.4 out of 10, Exceptional, (19)
"We had a wonderful weekend:)"
$265 nightly
The price is $293
Aug 19 - Aug 20
Total includes taxes and fees
Calm Country Oasis - Creek, ATV Trls & Norris Lake
Lakefront House at Summer Breeze w/ Private Dock w/ Kayaks
Relax in a hot tub overlooking a serene lake or pond, surrounded by lush greenery and a deck with barbecue facilities.

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

10.0 out of 10, Exceptional, (21)
"Host was amazing with their information and house had everything we needed!"
Lakefront House at Summer Breeze w/ Private Dock w/ Kayaks
Beautiful lakefront house with full kitchen, private dock, & hot tub
Terrace/patio

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

9.8 out of 10, Exceptional, (86)
"Five days of peace, quiet, birds signing and great views of the lake."
Beautiful lakefront house with full kitchen, private dock, & hot tub
9 bdrm covered dock, firepit and large bar on water, Baltic hot tub, sleeps 26,
Relax in a serene hot tub overlooking a tranquil lake, surrounded by lush greenery and a clear sky.

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

10.0 out of 10, Exceptional, (3)
"Awesome house!"
9 bdrm covered dock, firepit and large bar on water, Baltic hot tub, sleeps 26,
Lakefront home at Tumbling Run Estates w/ Kayaks
Enjoy cooking in this well-organized kitchen with a large island and stainless steel appliances.

Lakefront home at Tumbling Run Estates w/ Kayaks

9.8 out of 10, Exceptional, (17)
"Awesome house and location Gorgeous, convenient and lots of fun for all ages and big family.gatherings. We also rented a pontoon and it was great too! Planning our next trip! Highly recommend."
Lakefront home at Tumbling Run Estates w/ Kayaks
Family Affair, room 4 30, 15 Beds, 2 FULL Kitchens!!! Huge dock w 2 boat slips
Relax on the lakeside deck with a bench and chair, surrounded by lush greenery and a tranquil atmosphere.

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

10.0 out of 10, Exceptional, (89)
"The house have space for everyone the kitchens have a lots things to use."
Family Affair, room 4 30, 15 Beds, 2 FULL Kitchens!!! Huge dock w 2 boat slips
Cabin on water with Covered Boat Dock -Gentle Slope to Lake!
Step outside to a serene covered area with a wooden deck and porch, offering a view of the surrounding forest.

Cabin on water with Covered Boat Dock -Gentle Slope to Lake!

10.0 out of 10, Exceptional, (32)
"Great location, clean house, met all our needs! Hosts were always very responsive and made sure we had a great stay. We will be back!"
Cabin on water with Covered Boat Dock -Gentle Slope to Lake!
Lakeside Lodge- Dock, Hot Tub, Fire Pit+ 8 Kayaks
Relax in a spacious room with a comfortable seating area, dining space, and exposed wooden beams.

Lakeside Lodge- Dock, Hot Tub, Fire Pit+ 8 Kayaks

9.6 out of 10, Exceptional, (47)
"Very spacious and fun house with tons to do!"
Lakeside Lodge- Dock, Hot Tub, Fire Pit+ 8 Kayaks
Be the family hero - The Great Escape is Waterfrnt, 9 bdrms, with water slide
Relax on the patio with a metal table and chairs, surrounded by a brick wall and a rustic ceiling.

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

9.8 out of 10, Exceptional, (74)
"We had a wonderful time. The place had everything we needed, was clean, and provided the perfect setting for our family vacation. "
Be the family hero - The Great Escape is Waterfrnt, 9 bdrms, with water slide
Lake Front - Gorgeous views, 6 bedroom/ 6 1/2 baths, 2 refrigerators/dishwashers
Enjoy expansive views of the surrounding area from the upper-floor balcony, overlooking a serene natural landscape and a dock with a covered seating area.

Lake Front - Gorgeous views, 6 bedroom/ 6 1/2 baths, 2 refrigerators/dishwashers

10.0 out of 10, Exceptional, (18)
"The home had plenty of space to spread out and easy access to the lake! We had a great time!"
Lake Front - Gorgeous views, 6 bedroom/ 6 1/2 baths, 2 refrigerators/dishwashers
Treasure Cove, Waterfront, 9 Bed/9 Bath, Double Decker Dock, arcade games
Escape to a serene riverside retreat, where a tranquil river flows through a wooded area and a deck offers scenic views.

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

9.8 out of 10, Exceptional, (45)
"Loved the lake and the view."
Treasure Cove, Waterfront, 9 Bed/9 Bath, Double Decker Dock, arcade games
LAKE DAZE--Lakefront/No Wake/9br/12ba/Private Dock/Hot Tub/Sleeps 32
Enjoy cooking in this well-lit kitchen with a large window offering a view of the surrounding landscape.

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

9.6 out of 10, Exceptional, (65)
"Love the place super relaxing "
LAKE DAZE--Lakefront/No Wake/9br/12ba/Private Dock/Hot Tub/Sleeps 32
Book your fall retreat today!
Relax on the deck overlooking the serene water, surrounded by lush greenery and comfortable seating areas.

Book your fall retreat today!

10.0 out of 10, Exceptional, (46)
"So perfect place"
Book your fall retreat today!
Houseboat Retreat on Norris Lake
Relax on the rooftop terrace with a sofa and bench, taking in the breathtaking views of the surrounding landscape.

Houseboat Retreat on Norris Lake

10.0 out of 10, Exceptional, (1)
"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...
Houseboat Retreat on Norris Lake
Book now for Summer! We still have some prime dates available.
Situated by a serene lake, this gazebo offers a tranquil retreat with a flat roof and open sides, elevated for a scenic view.

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

9.6 out of 10, Exceptional, (25)
"We really enjoyed our stay! The property was beautiful!"
Book now for Summer! We still have some prime dates available.
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.
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Top Middlesboro Hotel Reviews

Econo Lodge Middlesboro

Econo Lodge Middlesboro

10/10 Excellent
"Staff was very friendly. "
Melissa 1-night trip
Posted 1 day ago
Econo Lodge Middlesboro

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?

9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock: 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 a selection of games 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.