Book Holiday Homes in Middlesboro
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Featured Holiday Homes in Middlesboro

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
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 |
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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 |
More accommodations in Middlesboro
Top trending hotels in Middlesboro

Sleep Inn & Suites

Econo Lodge Middlesboro

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

Holiday Inn Express Middlesboro by IHG
More ways to explore Middlesboro
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^Subject to availability and chosen travel dates.