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Middlesboro Vacation Rentals

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Check prices for these dates

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Jun 18 - Jun 19
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Jun 19 - Jun 20
This weekend
Jun 20 - Jun 22
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Jun 27 - Jun 29

Vacation Rentals in Middlesboro

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

8.4 out of 10, Very Good, (12)
"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
Fabulous view, walking distance from Flat Hollow Marina
Property grounds

Fabulous view, walking distance from Flat Hollow Marina

9.8 out of 10, Exceptional, (10)
"Perfect for all our needs, clean, close to the marina."
Fabulous view, walking distance from Flat Hollow Marina
9 bdrm covered dock, firepit and large bar on water, Baltic hot tub, sleeps 26,
Terrace/patio

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

10.0 out of 10, Exceptional, (1)
"This place was absolutely incredible! You can tell the owners have put lots of time and thought into making sure the stay is nothing short of amazing. The room themes are just so cool! The house was very clean, spacious, well maintained, and fully equipped with everything you may need. The host was very responsive and had great communication throughout the whole stay. The views of the lake from the house were absolutely stunning! We also rented a pontoon boat from them and the boat was in great...
9 bdrm covered dock, firepit and large bar on water, Baltic hot tub, sleeps 26,
Dog-friendly lake home with private floating dock - jetted tub, firepit, & decks
Dining

Dog-friendly lake home with private floating dock - jetted tub, firepit, & decks

7.6 out of 10, Good, (17)
"Overall, the cabin was decent. Enjoyed the rustic feel of it. All amenities worked well and there was sufficient room for multiple families. "
Dog-friendly lake home with private floating dock - jetted tub, firepit, & decks
Dog-friendly lakefront house with hot tub, central AC, & mountain view
Fridge, microwave, oven, stovetop

Dog-friendly lakefront house with hot tub, central AC, & mountain view

9.6 out of 10, Exceptional, (11)
"Loved the property, everything you need for a nice family lake vacation."
Dog-friendly lakefront house with hot tub, central AC, & mountain view
Beautiful Norris Lake Front A-Frame with Private Dock in Speedwell, Tn .
Property grounds

Beautiful Norris Lake Front A-Frame with Private Dock in Speedwell, Tn .

10.0 out of 10, Exceptional, (42)
"Wonderful vacation"
Beautiful Norris Lake Front A-Frame with Private Dock in Speedwell, Tn .
9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock
Smart TV, fireplace, DVD player, foosball

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

9.8 out of 10, Exceptional, (102)
"We went to ride the trails and enjoy the lake life. It was an awesome place. "
9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock
Waker's Paradise: Lakefront,9br/8.5ba, Private Dock,Hot Tub,Gameroom,Sleeps 32
Interior

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

9.6 out of 10, Exceptional, (43)
"Great experience- accurate listing that ensured space for all!"
Waker's Paradise: Lakefront,9br/8.5ba, Private Dock,Hot Tub,Gameroom,Sleeps 32
Lakefront House at Summer Breeze w/ Private Dock w/ Kayaks
Terrace/patio

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

10.0 out of 10, Exceptional, (19)
"Host was amazing with their information and house had everything we needed!"
Lakefront House at Summer Breeze w/ Private Dock w/ Kayaks
Lakefront home at Tumbling Run Estates w/ Kayaks
Fridge, microwave, oven, stovetop

Lakefront home at Tumbling Run Estates w/ Kayaks

9.8 out of 10, Exceptional, (15)
"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
Secluded No Wake Cove - Private Covered Dock-Screened Porch-Kayaks
Exterior

Secluded No Wake Cove - Private Covered Dock-Screened Porch-Kayaks

10.0 out of 10, Exceptional, (33)
"We had an amazing stay at Percy’s Cove. The home had everything we needed and was very clean. We would definitely stay here again!"
Secluded No Wake Cove - Private Covered Dock-Screened Porch-Kayaks
Paradise Cove on Norris Lake w/ Kayaks
TV, DVD player, table tennis

Paradise Cove on Norris Lake w/ Kayaks

9.8 out of 10, Exceptional, (30)
"Very enjoyable property."
Paradise Cove on Norris Lake w/ Kayaks
Slip-Away into Isolation & Relaxation w/ Covered Dock & Hot Tub.
Private kitchen

Slip-Away into Isolation & Relaxation w/ Covered Dock & Hot Tub.

10.0 out of 10, Exceptional, (1)
"Very good. Nice clean, spacious place with a good view of the river."
Slip-Away into Isolation & Relaxation w/ Covered Dock & Hot Tub.
Lakein' It Easy With Private Dock
Property grounds

Lakein' It Easy With Private Dock

9.8 out of 10, Exceptional, (30)
" Although we knew it was on a hill to the lake it is a very very sharp decent. While I understand winter pool our dock was completely out of the water. Luckily no one was staying next door and we could use theirs. Pictures of back yard are very deceiving"
Lakein' It Easy With Private Dock
Lake Front - Gorgeous views, 6 bedroom/ 6 1/2 baths, 2 refrigerators/dishwashers
Exterior

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

10.0 out of 10, Exceptional, (16)
"Amazing host and property, everything went perfect"
Lake Front - Gorgeous views, 6 bedroom/ 6 1/2 baths, 2 refrigerators/dishwashers
Charming Norris Lake Cabin with views and boat slip @ Marina!
2 bedrooms, free WiFi, bed sheets

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

2.0 star property
10.0 out of 10, Exceptional, (7)
"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!"
Charming Norris Lake Cabin with views and boat slip @ Marina!
Family Affair, room 4 30, 15 Beds, 2 FULL Kitchens!!! Huge dock w 2 boat slips
Property grounds

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

10.0 out of 10, Exceptional, (85)
"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
Lakefront home with private dock and boat launch - dog-friendly & central AC
Terrace/patio

Lakefront home with private dock and boat launch - dog-friendly & central AC

9.6 out of 10, Exceptional, (33)
"The house is very confortable , you will find everything you need for your vacations."
Lakefront home with private dock and boat launch - dog-friendly & central AC
Lakefront Cottage on Norris Lake
Fridge, microwave, oven, stovetop

Lakefront Cottage on Norris Lake

9.2 out of 10, Wonderful, (10)
"Short walk to boat and Marina. Great location. "
Lakefront Cottage on Norris Lake
Big Private Dock! 3 BRM, 2 Bath house 64 steps from the water, WIFI
Outdoor dining

Big Private Dock! 3 BRM, 2 Bath house 64 steps from the water, WIFI

9.8 out of 10, Exceptional, (6)
"Loved having dock for boat, Beautiful view of the lake from the porch"
Big Private Dock! 3 BRM, 2 Bath house 64 steps from the water, WIFI
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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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?

Fabulous view, walking distance from Flat Hollow Marina : This vacation home rental near Middlesboro is located on a lake and has a patio, a garden, 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.

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 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.