Book Holiday Homes in Middlesboro

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Featured Holiday Homes in Middlesboro

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

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

Speedwell
With a stay at this vacation home in Speedwell (Flat Hollow Marina), you'll be 21.3 mi (34.3 km) from Norris Lake and 7.9 mi (12.7 km) from Kincaid Historical ...
Secluded No Wake Cove - Private Covered Dock - Screened Porch - Kayaks - Netflix
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

Middlesboro
With a stay at this vacation home in Middlesboro, you'll be within a 5-minute drive of Middlesboro ARH Hospital and Bell County Historical Society Museum.
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
LAKE DAZE--Lakefront/No Wake/9br/12ba/Private Dock/Hot Tub/Sleeps 32

LAKE DAZE--Lakefront/No Wake/9br/12ba/Private Dock/Hot Tub/Sleeps 32

LaFollette
When you stay at this vacation home in La Follette, you'll be on the waterfront and 11 minutes by car from Sugar Hollow Marina.
LAKE DAZE--Lakefront/No Wake/9br/12ba/Private Dock/Hot Tub/Sleeps 32
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Lakefront w/ Private Dock, 7 BR,  Free Kayaks, Firepit, Hot Tub

Lakefront w/ Private Dock, 7 BR, Free Kayaks, Firepit, Hot Tub

Speedwell
With a stay at this vacation home in Speedwell (Flat Hollow Marina), you'll be 21.3 mi (34.2 km) from Norris Lake and 7.9 mi (12.7 km) from Kincaid Historical ...
Lakefront w/ Private Dock, 7 BR, Free Kayaks, Firepit, Hot Tub
Norris Nook: Lakefront 9br/11ba, Private Dock,Private HotTub,Sleeps 32, Gameroom

Norris Nook: Lakefront 9br/11ba, Private Dock,Private HotTub,Sleeps 32, Gameroom

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.
Norris Nook: Lakefront 9br/11ba, Private Dock,Private HotTub,Sleeps 32, Gameroom
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
Located in Maynardville, this vacation home is on the waterfront, within a 15-minute drive of Norris Lake and Narrow Ridge Earth Literacy Center.
Spacious, lakefront home with private dock, hot tub, chic decor, & amazing views
Sleeps 25/PRIVATE DOCK CHEF KITCHEN WITH ICE MAKER! Great fire pit, game area

Sleeps 25/PRIVATE DOCK CHEF KITCHEN WITH ICE MAKER! Great fire pit, game area

LaFollette
With a stay at this vacation home in La Follette (Lakeside Estates), you'll be 12 minutes by car from Sugar Hollow Marina.
Sleeps 25/PRIVATE DOCK CHEF KITCHEN WITH ICE MAKER! Great fire pit, game area
BOOK NOW FOR YOUR INTIMATE WINTER RETREAT!

BOOK NOW FOR YOUR INTIMATE WINTER RETREAT!

LaFollette
With a stay at this vacation home in La Follette (Lakeside Estates), you'll be 12 minutes by car from Sugar Hollow Marina.
BOOK NOW FOR YOUR INTIMATE WINTER RETREAT!
Lakefront Pet friendly Private covered dock

Lakefront Pet friendly Private covered dock

New Tazewell
With a stay at this vacation home in New Tazewell, you'll be on the waterfront, within a 15-minute drive of Norris Lake and Lone Mountain Boat Dock.
Lakefront Pet friendly Private covered dock
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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
131 Holiday Homes
Lowest Price
AU$105
Highest Price
AU$159
Popular accommodation
Secluded No Wake Cove - Private Covered Dock - Screened Porch - Kayaks - Netflix, Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals., LAKE DAZE--Lakefront/No Wake/9br/12ba/Private Dock/Hot Tub/Sleeps 32, Lakefront w/ Private Dock, 7 BR, Free Kayaks, Firepit, Hot Tub, Norris Nook: Lakefront 9br/11ba, Private Dock,Private HotTub,Sleeps 32, Gameroom, Spacious, lakefront home with private dock, hot tub, chic decor, & amazing views, Sleeps 25/PRIVATE DOCK CHEF KITCHEN WITH ICE MAKER! Great fire pit, game area, BOOK NOW FOR YOUR INTIMATE WINTER RETREAT!, Lakefront Pet friendly Private covered dock

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$159 per night from 6 Jan to 7 Jan
AU$159
includes taxes & fees
6 Jan - 7 Jan 2025
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$148 per night from 12 Jan to 13 Jan
AU$148
includes taxes & fees
12 Jan - 13 Jan 2025
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
Boone Trail Inn

Boone Trail Inn

2 out of 5
2105 US HIGHWAY 25 E, Middlesboro, KY
Fully refundableReserve now, pay when you stay
The price is AU$138 per night from 24 Dec to 25 Dec
AU$138
includes taxes & fees
24 Dec - 25 Dec
Located in Middlesboro, Boone Trail Inn is within a 5-minute drive of Middlesboro Mall and Bell County Historical Society Museum.
Boone Trail Inn
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Days Inn by Wyndham Jellico - Tennessee State Line

Days Inn by Wyndham Jellico - Tennessee State Line

2 out of 5
1417 5th Street, Jellico, TN
Fully refundableReserve now, pay when you stay
The price is AU$105 per night from 29 Dec to 30 Dec
AU$105
includes taxes & fees
29 Dec - 30 Dec
Located in Jellico, Days Inn by Wyndham Jellico - Tennessee State Line is in a state park, within a 5-minute drive of Indian Mountain State Park and Memorial ...
Days Inn by Wyndham Jellico - Tennessee State Line
Don't see what you're looking for?
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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.