Book Holiday Homes in Middlesboro

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Featured Holiday Homes in Middlesboro

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

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

LaFollette
When you stay at this vacation home in La Follette, you'll be on the waterfront and 12 minutes by car from Sugar Hollow Marina.
Waker's Paradise: Lakefront,9br/8.5ba, Private Dock,Hot Tub,Gameroom,Sleeps 32
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$324 per night from 21 Aug to 22 Aug
AU$324
21 Aug - 22 Aug
includes taxes & fees
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,
9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock

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

LaFollette
When you stay at this vacation home in La Follette, you'll be on the waterfront and 12 minutes by car from Sugar Hollow Marina.
9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock
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Lakefront House at Summer Breeze w/ Private Dock w/ Kayaks

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

New Tazewell
With a stay at this vacation home in New Tazewell, you'll be on the waterfront, within a 10-minute drive of Norris Lake and Straight Creek Boat Dock.
Lakefront House at Summer Breeze w/ Private Dock w/ Kayaks
Cabin on water with Covered Boat Dock -Gentle Slope to Lake!

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

LaFollette
With a stay at this vacation home in La Follette, you'll be on the waterfront, and 14.5 mi (23.3 km) from Norris Lake and 7.2 mi (11.5 km) from Sugar Hollow ...
Cabin on water with Covered Boat Dock -Gentle Slope to Lake!
Be the family hero - The Great Escape is Waterfrnt, 9 bdrms, with water slide

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

La Follette
With a stay at this vacation home in La Follette (Lakeside Estates), you'll be 12 minutes by car from Sugar Hollow Marina.
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

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

LaFollette
With a stay at this vacation home in La Follette, you'll be on the waterfront, and 5.4 mi (8.7 km) from Sugar Hollow Marina and 5.6 mi (9.1 km) from Kincaid ...
Lake Front - Gorgeous views, 6 bedroom/ 6 1/2 baths, 2 refrigerators/dishwashers
NEW LISTING! 5Bed 3Bath Lakefront Retreat, 2 slip dock, sun deck & slide!

NEW LISTING! 5Bed 3Bath Lakefront Retreat, 2 slip dock, sun deck & slide!

LaFollette
With a stay at this vacation home in La Follette, you'll be 28.6 mi (46 km) from Norris Lake and 5 mi (8 km) from Kincaid Historical Monument.
NEW LISTING! 5Bed 3Bath Lakefront Retreat, 2 slip dock, sun deck & slide!
Lakefront Getaway at Swan Seymour w/ Kayaks

Lakefront Getaway at Swan Seymour w/ Kayaks

Maynardville
With a stay at this vacation home in Maynardville, you'll be on the waterfront, just steps from Norris Lake.
Lakefront Getaway at Swan Seymour w/ Kayaks
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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
179 Holiday Homes
Lowest Price
AU$149
Highest Price
AU$324
Popular accommodation
Waker's Paradise: Lakefront,9br/8.5ba, Private Dock,Hot Tub,Gameroom,Sleeps 32, 4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky, , 9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock, Lakefront House at Summer Breeze w/ Private Dock w/ Kayaks, Cabin on water with Covered Boat Dock -Gentle Slope to Lake!, 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, NEW LISTING! 5Bed 3Bath Lakefront Retreat, 2 slip dock, sun deck & slide!, Lakefront Getaway at Swan Seymour w/ Kayaks

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$161 per night from 31 Aug to 1 Sept
AU$161
31 Aug - 1 Sept
includes taxes & fees
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$149 per night from 17 Aug to 18 Aug
AU$149
17 Aug - 18 Aug
includes taxes & fees
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
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$215 per night from 24 Aug to 25 Aug
AU$215
24 Aug - 25 Aug
includes taxes & fees
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
Save an average of 15% on thousands of hotels when you're signed in
Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG

2.5 out of 5
56 West Highway 92, Williamsburg, KY
Fully refundable
The price is AU$217 per night from 7 Sept to 8 Sept
AU$217
7 Sept - 8 Sept
includes taxes & fees
Located in Williamsburg, Holiday Inn Express Williamsburg by IHG is in the mountains, a 2-minute drive from Kentucky Splash Water Park and 14 minutes from Memorial ...
Holiday Inn Express Williamsburg 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.