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
With a stay at this vacation home in Maynardville, you'll be on the waterfront, just steps from Norris Lake.
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
With a stay at this vacation home in Maynardville, you'll be on the waterfront, within a 15-minute drive of Norris Lake and Narrow Ridge Earth Literacy ...
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
With a stay at this vacation home in Maynardville, you'll be on the waterfront, within a 15-minute drive of Norris Lake and Narrow Ridge Earth Literacy ...
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
With a stay at this vacation home in Speedwell (Flat Hollow Marina), you'll be 23.1 mi (37.2 km) from Norris Lake and 9.8 mi (15.7 km) from Kincaid Historical ...
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 AU$411 per night from 4 Apr to 5 Apr
AU$411
includes taxes & fees
4 Apr - 5 Apr
A stay at this vacation home places you in the heart of Cumberland Gap, steps from Cumberland Gap National Historical Park and 3 minutes by foot from Lincoln ...
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
With a stay at this vacation home in Maynardville, you'll be on the waterfront, just steps from Norris Lake.
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
When you stay at this vacation home in New Tazewell, you'll be on the waterfront and 13 minutes by car from Norris Lake.
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
With a stay at this vacation home in Maynardville, you'll be on the waterfront, within a 15-minute drive of Norris Lake and Narrow Ridge Earth Literacy ...
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
With a stay at this vacation home in Maynardville, you'll be on the waterfront, just steps from Norris Lake.
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
183 Holiday Homes
Lowest Price
AU$151
Highest Price
AU$411
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 AU$164 per night from 20 Apr to 21 Apr
AU$164
includes taxes & fees
20 Apr - 21 Apr
With a stay at Sleep Inn & Suites in Middlesboro, you'll be 1.3 mi (2.1 km) from Cumberland Gap National Historical Park and 10.9 mi (17.6 km) from Pine Mountain ...
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 AU$151 per night from 20 Apr to 21 Apr
AU$151
includes taxes & fees
20 Apr - 21 Apr
When you stay at Econo Lodge Middlesboro in Middlesboro, you'll be in the mountains, within a 10-minute walk of Cumberland Gap National Historical Park and Bell ...
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 AU$335 per night from 13 Apr to 14 Apr
AU$335
includes taxes & fees
13 Apr - 14 Apr
With a stay at this vacation home in Middlesboro, you'll be within a 5-minute drive of Bell County Historical Society Museum and Middlesboro ARH Hospital.
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 AU$206 per night from 13 Apr to 14 Apr
AU$206
includes taxes & fees
13 Apr - 14 Apr
With a stay at Holiday Inn Express Middlesboro by IHG in Middlesboro, you'll be in a national park, a 4-minute walk from Middlesboro Mall and a 2-minute drive ...
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.