Book Holiday Homes in Middlesboro

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Featured Holiday Homes in Middlesboro

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

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

Maynardville
Stay at this vacation home in Maynardville. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Basketball Court and Narrow ...
Beautiful lakefront house with full kitchen, private dock, & hot tub
Spacious, lakefront home with private dock, hot tub, chic decor, & amazing views

Spacious, lakefront home with private dock, hot tub, chic decor, & amazing views

Maynardville
Stay at this vacation home in Maynardville. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Narrow Ridge Earth Literacy Center and ...
Spacious, lakefront home with private dock, hot tub, chic decor, & amazing views
Brand New Lake House on Norris Lake ~ Includes Paddle Boards and Kayaks!

Brand New Lake House on Norris Lake ~ Includes Paddle Boards and Kayaks!

Maynardville
Stay at this vacation home in Maynardville. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Narrow Ridge Earth Literacy Center and ...
Brand New Lake House on Norris Lake ~ Includes Paddle Boards and Kayaks!
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Beautiful Norris Lake Front A-Frame with Private Dock in Speedwell, Tn .

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

Speedwell
Stay at this vacation home in Speedwell. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Kincaid Historical Monument and Chuck Swan ...
Beautiful Norris Lake Front A-Frame with Private Dock in Speedwell, Tn .
1928 Home in the heart of Cumberland Gap

1928 Home in the heart of Cumberland Gap

Cumberland Gap
The price is NZ$448 per night from 3 Apr to 4 Apr
NZ$448
includes taxes & fees
3 Apr - 4 Apr
Stay at this vacation home in Cumberland Gap. Enjoy a garden, an in-room coffeemaker, and air conditioning. Popular attractions Cumberland Gap National Historical ...
1928 Home in the heart of Cumberland Gap
Waterfront home with game room, theater, deck, dock & fireplace

Waterfront home with game room, theater, deck, dock & fireplace

Maynardville
Book a stay at this family-friendly vacation home in Maynardville. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions ...
Waterfront home with game room, theater, deck, dock & fireplace
Dog-friendly lakefront house with hot tub, central AC, & mountain view

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

New Tazewell
Stay at this vacation home in New Tazewell. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Lone Mountain Boat Dock and Narrow ...
Dog-friendly lakefront house with hot tub, central AC, & mountain view
Norris lakefront home with covered boat dock

Norris lakefront home with covered boat dock

Maynardville
Stay at this vacation home in Maynardville. Enjoy free WiFi, a garden, and patios. Popular attractions Narrow Ridge Earth Literacy Center and Basketball Court ...
Norris lakefront home with covered boat dock
Lovely lakefront home with fire pit, fireplace, dock and gas grill

Lovely lakefront home with fire pit, fireplace, dock and gas grill

2 out of 5
Maynardville
Stay at this vacation home in Maynardville. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Norris Lake and Rabbit Island are located ...
Lovely lakefront home with fire pit, fireplace, dock and gas grill
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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.

Middlesboro Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Middlesboro vacation homes are the perfect way for you to wing it.

Holiday houses in Middlesboro let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Middlesboro in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Middlesboro adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Middlesboro with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Middlesboro vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Middlesboro Holiday Homes essential information

Accommodation
165 Holiday Homes
Lowest Price
NZ$166
Highest Price
NZ$448
Popular accommodation
Beautiful lakefront house with full kitchen, private dock, & hot tub, Spacious, lakefront home with private dock, hot tub, chic decor, & amazing views, Brand New Lake House on Norris Lake ~ Includes Paddle Boards and Kayaks!, Beautiful Norris Lake Front A-Frame with Private Dock in Speedwell, Tn ., 1928 Home in the heart of Cumberland Gap, Waterfront home with game room, theater, deck, dock & fireplace, Dog-friendly lakefront house with hot tub, central AC, & mountain view, Norris lakefront home with covered boat dock, Lovely lakefront home with fire pit, fireplace, dock and gas grill

Top trending hotels in Middlesboro

Sleep Inn & Suites

Sleep Inn & Suites

2.5 out of 5
1260 N, 12th Street, Middlesboro, KY
Fully refundableReserve now, pay when you stay
The price is NZ$182 per night from 20 Apr to 21 Apr
NZ$182
includes taxes & fees
20 Apr - 21 Apr
Book a stay at this business-friendly hotel in Middlesboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Sleep Inn & Suites
Econo Lodge Middlesboro

Econo Lodge Middlesboro

2 out of 5
1623 Cumberland Avenue, Middlesboro, KY
Fully refundableReserve now, pay when you stay
The price is NZ$166 per night from 13 Apr to 14 Apr
NZ$166
includes taxes & fees
13 Apr - 14 Apr
Stay at this motel in Middlesboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Econo Lodge Middlesboro
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,

4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,

Middlesboro
The price is NZ$373 per night from 5 Apr to 6 Apr
NZ$373
includes taxes & fees
5 Apr - 6 Apr
Stay at this vacation home in Middlesboro. Enjoy free WiFi, a garden, and patios. Popular attractions Bell County Historical Society Museum and Middlesboro Country ...
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
Save an average of 15% on thousands of hotels when you're signed in
Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG

2.5 out of 5
1252 N 12th St, Middlesboro, KY
Fully refundable
The price is NZ$226 per night from 13 Apr to 14 Apr
NZ$226
includes taxes & fees
13 Apr - 14 Apr
Book a stay at this business-friendly hotel in Middlesboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Holiday Inn Express Middlesboro by IHG
Don't see what you're looking for?
See all available properties in Middlesboro
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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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^Subject to availability and chosen travel dates.