Holiday Homes in Middlesboro

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Apartments
Apartments
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Cabins
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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Middlesboro holiday homes

A kitchen with light blue cabinets, a black microwave, a sink, and a stove.

1. House close to ARH Hospital, Tackett Creek & LMU!

House close to ARH Hospital, Tackett Creek & 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$462
includes taxes & fees
9 Dec - 10 Dec
House close to ARH Hospital, Tackett Creek & LMU!
A neatly made bed with patterned bedding, a bedside table with a lamp, and a curtain.

2. Private bungalow close to LMU, ARH, Cumberland Gap

Private bungalow close to LMU, ARH, Cumberland Gap
Middlesboro
8.0 out of 10, Very good, (1 review)
"This house was conveniently located. Upstairs bedroom was hot but everything else was nice."
United States
Leann L.
The price is AU$447
includes taxes & fees
17 Nov - 18 Nov
Private bungalow close to LMU, ARH, Cumberland Gap
A portable barbecue grill with a black and green design, mounted on a metal stand with adjustable legs.

3. Gorgeous 4-bedroom house in Middlesboro KY with WiFi, AC. Minutes from LMU

Gorgeous 4-bedroom house in Middlesboro KY with WiFi, AC. Minutes from LMU
Middlesboro
10.0 out of 10, Exceptional, (20 reviews)
"Lots of room. Clean. Good host."
United States
Konnie D.
The price is AU$541
includes taxes & fees
16 Nov - 17 Nov
Gorgeous 4-bedroom house in Middlesboro KY with WiFi, AC. Minutes from LMU
An outdoor patio with a wooden ceiling, string lights, a sofa, chairs, and a table.

4. 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, (9 reviews)
"We enjoyed our stay. "
United States
Emily S.
The price is AU$436
includes taxes & fees
13 Dec - 14 Dec
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
A brick house with a covered porch, a front door, and a small garden area with potted plants.

5. 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$479
includes taxes & fees
13 Nov - 14 Nov
Welcoming 3-bedroom house with AC in charming Middlesboro
An aerial view of a campus with multiple buildings, a central tower, and a large open grassy area.

6. Blissful Bungalow across from LMU campus

Blissful Bungalow across from LMU campus
Harrogate
9.6 out of 10, Exceptional, (46 reviews)
"Very convenient to everything we needed to do, very clean and neat"
United States
Brandi L.
The price is AU$316
includes taxes & fees
19 Nov - 20 Nov
Blissful Bungalow across from LMU campus
A wooden deck with two chairs and a small table, overlooking a green landscape.

7. Harrogate Home Mountain View’s Dog Friendly

Harrogate Home Mountain View’s Dog Friendly
Harrogate
10.0 out of 10, Exceptional, (32 reviews)
"Great place to stay. "
United States
Jodi D.
The price is AU$429
includes taxes & fees
17 Nov - 18 Nov
Harrogate Home Mountain View’s Dog Friendly
A wooden deck with a railing, a brick building, and a door with a window.

8. 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, (13 reviews)
"Clean and quiet place to stay when visiting the area. Will definitely consider this place again when we visit Pineville again! "
United States
seth r.
The price is AU$421
includes taxes & fees
17 Nov - 18 Nov
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
A covered deck with wicker furniture and a glass table.

9. Peaceful & Private! Pet-Friendly Williamsburg Home

Peaceful & Private! Pet-Friendly Williamsburg Home
Williamsburg
10.0 out of 10, Exceptional, (6 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$427
includes taxes & fees
17 Nov - 18 Nov
Peaceful & Private! Pet-Friendly Williamsburg Home
A covered outdoor seating area with a sofa, chairs, and planters.

10. 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$477
includes taxes & fees
6 Dec - 7 Dec
LMU Pine Mtn State Park Cumberland Gap Laurel Cove
An outdoor covered patio with a table and chairs, a barbecue grill, and a view of a wooden house.

11. Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg

Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg
Williamsburg
10.0 out of 10, Exceptional, (1 review)
"Had a wonderful stay at this cabin. It was very beautiful and the location was very peaceful and quiet but not too far from other things. Would definitely need a 4 wheel drive vehicle to get to the cabin. The host was very nice and had great communication. Definitely recommend this cabin for anyone looking to relax and enjoy nature."
United States
Nancy A.
The price is AU$474
includes taxes & fees
17 Nov - 18 Nov
Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg
An outdoor patio with a wooden table and wicker chairs.

12. Park Ave Laurel Cove, Bell Theatre & LMU

Park Ave Laurel Cove, Bell Theatre & LMU
Pineville
9.4 out of 10, Exceptional, (6 reviews)
"Such a cute little place we have stayed twice already"
United States
Cassie S.
The price is AU$516
includes taxes & fees
14 Nov - 15 Nov
Park Ave Laurel Cove, Bell Theatre & LMU
An outdoor patio with a pergola, four wicker chairs, a round table, and a view of a green landscape.

13. 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
9.2 out of 10, Wonderful, (31 reviews)
"Our stay was great! Great location and enough bedrooms for our 5 guests at an amazing price point. The host was very responsive as well! Will be staying again."
United States
Rachel W.
The price is AU$255
includes taxes & fees
13 Nov - 14 Nov
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
A wooden deck with outdoor furniture, including a table and a sofa, surrounded by a wooden railing.

14. Forget your worries in this spacious 5-Bedroom Home in Downtown Barbourville.

Forget your worries in this spacious 5-Bedroom Home in Downtown Barbourville.
Barbourville
10.0 out of 10, Exceptional, (11 reviews)
"Our group had a wonderful stay! The house is gorgeous from top to bottom and had literally everything we needed! "
United States
Jessica S.
The price is AU$755
includes taxes & fees
15 Nov - 16 Nov
Forget your worries in this spacious 5-Bedroom Home in Downtown Barbourville.
A wooden deck with two chairs facing a scenic view of green hills and a lake.

15. MOUNTAIN TOP CABIN WITH PARTNERING MARINA ON NORRIS LAKE

MOUNTAIN TOP CABIN WITH PARTNERING MARINA ON NORRIS LAKE
Rock Harbor
9.6 out of 10, Exceptional, (32 reviews)
"The cabin is awesome. The marina is right down the road. Everything was great, I would definitely stay here again"
United States
Robert R.
The price is AU$827
includes taxes & fees
24 Nov - 25 Nov
MOUNTAIN TOP CABIN WITH PARTNERING MARINA ON NORRIS LAKE
A covered outdoor area with a table and chairs, overlooking a body of water and a town.

16. 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, (51 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$1,022
includes taxes & fees
15 Nov - 16 Nov
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.
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Learn more about Middlesboro

Nestled in the Appalachian Mountains, Middlesboro invites you to explore the historic Cumberland Gap National Historical Park. Tee off at the scenic Middlesboro Country Club or delve into local heritage at the Bell County Historical Society Museum.

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

Top reviews in Middlesboro

A natural setting with a clear pond surrounded by rocks and trees, and rows of blue chairs arranged for an event.
Pine Mountain State Resort Park

Pine Mountain State Resort Park

Pine Mountain State Resort Park
Pineville

10/10 Excellent

To get the most of this lovely venue try and stay several days. The staff in all departments are enthusiastic, welcoming and friendly and went out of their way to make sure we enjoyed our brief stay. Our room overlooked the valley and had all the comforts we needed. The restaurant is not expensive nor overpriced (as many specialty venues tend to be), with a talented chef producing yummy meals. Highly recommended.
Australia
Richard
Reviewed July 13, 2017
Pine Mountain State Resort Park