Book Holiday Homes in Middlesboro

Start date: Check-in selected.
To Date
End date: Check-out

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Middlesboro

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

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

LaFollette TN
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.
Opens in a new window9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock
Lakefront w/ Private Dock, 7 BR,  Free Kayaks, Firepit, Hot Tub

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

Speedwell TN
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 ...
Opens in a new windowLakefront w/ Private Dock, 7 BR, Free Kayaks, Firepit, Hot Tub
Norris Lake Cabin – Game Room, Dock & Stunning Views

Norris Lake Cabin – Game Room, Dock & Stunning Views

New Tazewell TN
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.
Opens in a new windowNorris Lake Cabin – Game Room, Dock & Stunning Views
Save an average of 15% on thousands of hotels when you're signed in
Family Affair, room 4  30, 15 Beds, 2 FULL Kitchens!!! Huge dock w 2 boat slips

Family Affair, room 4 30, 15 Beds, 2 FULL Kitchens!!! Huge dock w 2 boat slips

La Follette TN
With a stay at this vacation home in La Follette (Lakeside Estates), you'll be 11 minutes by car from Sugar Hollow Marina.
Opens in a new windowFamily Affair, room 4 30, 15 Beds, 2 FULL Kitchens!!! Huge dock w 2 boat slips
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 TN
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.
Opens in a new windowWaker's Paradise: Lakefront,9br/8.5ba, Private Dock,Hot Tub,Gameroom,Sleeps 32
American Freedom; Theater Rm! Enjoy the Fall Colors! Flexible Chk-in & out times

American Freedom; Theater Rm! Enjoy the Fall Colors! Flexible Chk-in & out times

Lafollette TN
With a stay at this vacation home in La Follette, you'll be on the waterfront, and 5.6 mi (9 km) from Sugar Hollow Marina and 5.7 mi (9.1 km) from Kincaid Historical ...
Opens in a new windowAmerican Freedom; Theater Rm! Enjoy the Fall Colors! Flexible Chk-in & out times
   Lake front home, Hot tub, Boat dock near Flat Hollow Marina in Speedwell Tn.

Lake front home, Hot tub, Boat dock near Flat Hollow Marina in Speedwell Tn.

Speedwell TN
With a stay at this vacation home in Speedwell (Flat Hollow Marina), you'll be 22.6 mi (36.3 km) from Norris Lake and 9.2 mi (14.8 km) from Kincaid Historical ...
Opens in a new window Lake front home, Hot tub, Boat dock near Flat Hollow Marina in Speedwell Tn.
ATV Trail Access! Secluded Mountain Retreat

ATV Trail Access! Secluded Mountain Retreat

Duff TN
With a stay at this vacation home in Duff, you'll be within a 15-minute drive of Norris Lake and Campbell County Historical Society.
Opens in a new windowATV Trail Access! Secluded Mountain Retreat
Blissful Bungalow across from LMU campus

Blissful Bungalow across from LMU campus

Harrogate TN
The price is AU$336 per night from 19 Jan to 20 Jan
AU$336
19 Jan - 20 Jan
includes taxes & fees
With a stay at this vacation home in Harrogate, you'll be steps from Lincoln Memorial University and a 2-minute drive from Cumberland Gap National Historical ...
Opens in a new windowBlissful Bungalow across from LMU campus
Don't see what you're looking for?
See all available properties in Middlesboro
View all properties
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
173 Holiday Homes
Lowest Price
AU$125
Highest Price
AU$336
Popular accommodation
9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock, Lakefront w/ Private Dock, 7 BR, Free Kayaks, Firepit, Hot Tub, Norris Lake Cabin – Game Room, Dock & Stunning Views, Family Affair, room 4 30, 15 Beds, 2 FULL Kitchens!!! Huge dock w 2 boat slips, Waker's Paradise: Lakefront,9br/8.5ba, Private Dock,Hot Tub,Gameroom,Sleeps 32, American Freedom; Theater Rm! Enjoy the Fall Colors! Flexible Chk-in & out times, Lake front home, Hot tub, Boat dock near Flat Hollow Marina in Speedwell Tn., ATV Trail Access! Secluded Mountain Retreat, Blissful Bungalow across from LMU campus

Top trending hotels in Middlesboro

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

2.5 out of 5
1260 N, 12th Street Middlesboro KY
Fully refundable
The price is AU$154 per night from 8 Feb to 9 Feb
AU$154
8 Feb - 9 Feb
includes taxes & fees
With a stay at Sleep Inn & Suites Middlesboro in Middlesboro, you'll be 1.5 mi (2.4 km) from Cumberland Gap National Historical Park and 11.1 mi (17.9 km) from ...
Opens in a new windowSleep Inn & Suites 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$206 per night from 8 Feb to 9 Feb
AU$206
8 Feb - 9 Feb
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 ...
Opens in a new windowHoliday Inn Express Middlesboro by IHG
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$147 per night from 11 Feb to 12 Feb
AU$147
11 Feb - 12 Feb
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 ...
Opens in a new windowEcono Lodge Middlesboro
Save an average of 15% on thousands of hotels when you're signed in
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$125 per night from 10 Feb to 11 Feb
AU$125
10 Feb - 11 Feb
includes taxes & fees
Located in Middlesboro, Boone Trail Inn is within a 5-minute drive of Middlesboro Mall and Bell County Historical Society Museum.
Opens in a new windowBoone Trail Inn
Don't see what you're looking for?
See all available properties in Middlesboro
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.