An aerial view of a town surrounded by mountains, with a mix of residential and commercial buildings, and a highway running through the center.

Holiday Homes in Middlesboro

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
10 July - 12 July
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Middlesboro holiday homes

Desk, iron/ironing board, WiFi, bed sheets

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
9.2 out of 10, Wonderful, (5 reviews)
"We enjoyed our stay. "
United States
Emily S.
The price is AU$513
includes taxes & fees
28 June - 29 June
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Dining

Private bungalow close to LMU, ARH, Cumberland Gap

Private bungalow close to LMU, ARH, Cumberland Gap
Middlesboro
The price is AU$428
includes taxes & fees
8 July - 9 July
Private bungalow close to LMU, ARH, Cumberland Gap
Exterior

Welcoming 3-bedroom house with AC in charming Middlesboro

Welcoming 3-bedroom house with AC in charming Middlesboro
Middlesboro
8.0 out of 10, Very good, (3 reviews)
"Great area to stay in "
United States
Corinna E.
The price is AU$494
includes taxes & fees
28 July - 29 July
Welcoming 3-bedroom house with AC in charming Middlesboro
Interior

Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU

Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
Middlesboro
7.4 out of 10, Good, (3 reviews)
"Advertised would sleep 12, yes it had beds for 12, but I guess we were to share towels , could be cleaner, food and trash under sofa cushions. Had to hunt for the WiFi password."
United States
Elita W.
The price is AU$577
includes taxes & fees
28 July - 29 July
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
Exterior

Blissful Bungalow across from LMU campus

Blissful Bungalow across from LMU campus
Harrogate
9.6 out of 10, Exceptional, (36 reviews)
"Very convenient to everything we needed to do, very clean and neat"
United States
Brandi L.
The price is AU$349
includes taxes & fees
1 July - 2 July
Blissful Bungalow across from LMU campus
Terrace/patio

Peaceful & Private! Pet-Friendly Williamsburg Home

Peaceful & Private! Pet-Friendly Williamsburg Home
Williamsburg
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful peaceful setting, great views! Host was very nice and helpful! Home was very clean and comfortable. Pet friendly, and kid friendly :)Highly recommend!"
United States
Alicia M.
The price is AU$447
includes taxes & fees
2 July - 3 July
Peaceful & Private! Pet-Friendly Williamsburg Home
Interior

The Lodge Cabin ~Norris Lake Views and Mountain Backdrops

The Lodge Cabin ~Norris Lake Views and Mountain Backdrops
New Tazewell
10.0 out of 10, Exceptional, (1 review)
"It was a lovely little home! Very clean and perfect for my family!"
United States
Lauren W.
The price is AU$326
includes taxes & fees
28 June - 29 June
The Lodge Cabin ~Norris Lake Views and Mountain Backdrops
Terrace/patio

Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina

Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
Speedwell
9.4 out of 10, Exceptional, (22 reviews)
"Was in a great location to be able to go to multiple riding locations. "
United States
Sara R.
The price is AU$282
includes taxes & fees
13 July - 14 July
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
Property grounds

Charming 3-bedroom house with WiFi, AC in Pineville Kentucky

Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Pineville
10.0 out of 10, Exceptional, (8 reviews)
"Property was very, very comfortable, clean and convenient. Well equipped. Extremely comfortable beds. We all slept like babies. Pretty yard and surrounding area. Highly recommend."
United States
Lee
The price is AU$447
includes taxes & fees
30 June - 1 July
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Fridge, microwave, oven, stovetop

Harrogate Home Mountain View’s Dog Friendly

Harrogate Home Mountain View’s Dog Friendly
Harrogate
10.0 out of 10, Exceptional, (25 reviews)
"Great place to stay. "
United States
Jodi D.
The price is AU$446
includes taxes & fees
1 July - 2 July
Harrogate Home Mountain View’s Dog Friendly
Interior

Mountain-View Suite Near I-75 EV Charging

Mountain-View Suite Near I-75 EV Charging
Jellico
The price is AU$369
includes taxes & fees
13 July - 14 July
Mountain-View Suite Near I-75 EV Charging
Terrace/patio

LMU Pine Mtn State Park Cumberland Gap Laurel Cove

LMU Pine Mtn State Park Cumberland Gap Laurel Cove
Pineville
10.0 out of 10, Exceptional, (1 review)
"Well cared for property with nice upgrades! Perfect for our stay, everything we needed, and accommodating. "
United States
Hope C.
The price is AU$509
includes taxes & fees
19 July - 20 July
LMU Pine Mtn State Park Cumberland Gap Laurel Cove
Exterior detail

Min. to Laurel Cove, LMU & Union, & Bell Theater

Min. to Laurel Cove, LMU & Union, & Bell Theater
Pineville
4.8 out of 10, (3 reviews)
"I did not stay at this property due to a double booking. I stayed at a nearby house that needs to be cleaned better, specially the floors, a shower curtain needs to be added to the beautiful update in bathroom, some plates woukd be nice. House rules and check in, check out procedures, places to visit and eat nearby would have been helpful to have posted at the house. Overall was a decent place to stay, quiet neighborhood. I would at least consider staying again."
United States
Stephanie F.
The price is AU$391
includes taxes & fees
19 July - 20 July
Min. to Laurel Cove, LMU & Union, & Bell Theater
TV

MOUNTAIN TOP CABIN WITH PARTNERING MARINA ON NORRIS LAKE

MOUNTAIN TOP CABIN WITH PARTNERING MARINA ON NORRIS LAKE
Rock Harbor
9.8 out of 10, Exceptional, (27 reviews)
"Great location for family gathering near local relatives. Beautiful views and close to New Tazewell. "
United States
Pamela D.
The price is AU$918
includes taxes & fees
9 July - 10 July
MOUNTAIN TOP CABIN WITH PARTNERING MARINA ON NORRIS LAKE
Property grounds

Norris Lake Cabin – Game Room, Dock & Stunning Views

Norris Lake Cabin – Game Room, Dock & Stunning Views
New Tazewell
9.8 out of 10, Exceptional, (13 reviews)
"Awesome place to stay. Friendly owners. Lake is beautiful. Would stay here again "
United States
Taryn T.
The price is AU$1,074
includes taxes & fees
30 June - 1 July
Norris Lake Cabin – Game Room, Dock & Stunning Views
Terrace/patio

Lake Front ★ No Wake w/ Dock ★ Gameroom ★ Carved FirePit ★ 2nd House Available

Lake Front ★ No Wake w/ Dock ★ Gameroom ★ Carved FirePit ★ 2nd House Available
LaFollette
10.0 out of 10, Exceptional, (47 reviews)
"House was spectacular, beds were very comfortable, plenty to do in the area and the lake was just beautiful. Would definitely stay here again!"
United States
Brooke R.
The price is AU$1,949
includes taxes & fees
30 June - 1 July
Lake Front ★ No Wake w/ Dock ★ Gameroom ★ Carved FirePit ★ 2nd House Available
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middlesboro Hotel Reviews

Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG

10/10 Excellent
"We checked in around 8pm and were greeted by the front desk staff was fantastic. They interacted with my 11-year-old great-niece in the best way. Sharing jokes and talking to her directly on her level. Of course, the adults felt comfortable and welcome as well. The pool was very nice and clean. The room was nice as well. We had no issues."
Donna 1-night trip
Posted 16 hours ago
Holiday Inn Express Middlesboro by IHG

Find out more about Middlesboro

Middlesboro Holiday Homes information

Number of reviews
150
Accommodation
178 Holiday Homes
Lowest Price
AU$282
Highest Price
AU$1,949