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

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Middlesboro holiday homes

A living room with a stone fireplace, wooden walls, a sofa, a coffee table, and a TV mounted on the wall.

1. 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, (19 reviews)
"Lots of room. Clean. Good host."
United States
Konnie D.
Gorgeous 4-bedroom house in Middlesboro KY with WiFi, AC. Minutes from LMU
A dining area with a table set for four, a ceiling fan, and a sign above reading 'BE OUR GUEST'.

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 NZ$571
includes taxes & fees
4 Nov - 5 Nov
Private bungalow close to LMU, ARH, Cumberland Gap
A living room with a TV on a wooden stand, a white chair, a small table, and a sofa.

3. 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 NZ$670
includes taxes & fees
19 Nov - 20 Nov
House close to ARH Hospital, Tackett Creek & LMU!
A bedroom with a bed, pillows, a nightstand, a lamp, a window with blinds, and a kitchen area with a refrigerator.

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
9.0 out of 10, Wonderful, (8 reviews)
"We enjoyed our stay. "
United States
Emily S.
The price is NZ$673
includes taxes & fees
27 Oct - 28 Oct
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 NZ$667
includes taxes & fees
27 Oct - 28 Oct
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, (43 reviews)
"Very convenient to everything we needed to do, very clean and neat"
United States
Brandi L.
The price is NZ$386
includes taxes & fees
5 Nov - 6 Nov
Blissful Bungalow across from LMU campus
A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a sign reading "EVERYDAY COOKING".

7. Harrogate Home Mountain View’s Dog Friendly

Harrogate Home Mountain View’s Dog Friendly
Harrogate
10.0 out of 10, Exceptional, (31 reviews)
"Great place to stay. "
United States
Jodi D.
The price is NZ$488
includes taxes & fees
27 Oct - 28 Oct
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 NZ$532
includes taxes & fees
27 Oct - 28 Oct
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
A covered outdoor deck with wooden flooring and metal chairs.

9. Peaceful & Private! Pet-Friendly Williamsburg Home

Peaceful & Private! Pet-Friendly Williamsburg Home
Williamsburg
10.0 out of 10, Exceptional, (5 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 NZ$544
includes taxes & fees
29 Oct - 30 Oct
Peaceful & Private! Pet-Friendly Williamsburg Home
A spacious living room with wooden beams, leather sofas, a wooden coffee table, and a mounted deer head.

10. 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 NZ$604
includes taxes & fees
27 Oct - 28 Oct
Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg
A covered outdoor seating area with a sofa, chairs, and planters.

11. 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 NZ$606
includes taxes & fees
5 Nov - 6 Nov
LMU Pine Mtn State Park Cumberland Gap Laurel Cove
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 NZ$654
includes taxes & fees
27 Oct - 28 Oct
Park Ave Laurel Cove, Bell Theatre & LMU
An outdoor patio with a fire pit, surrounded by chairs and a pergola with string lights.

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, (30 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 NZ$319
includes taxes & fees
27 Oct - 28 Oct
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
A modern kitchen with white cabinets, a stainless steel refrigerator, a wooden island with chairs, and a window providing natural light.

14. Norris Lake Cabin Getaway, Sleeps 6・View・Fire pit

Norris Lake Cabin Getaway, Sleeps 6・View・Fire pit
New Tazewell
8.0 out of 10, Very good, (1 review)
"It is a lovely dated home. We felt comfortable in our stay. It is situated between two curves so pulling in and out with a truck and trailer is a bit difficult as cars fly on that road. Other then that it had everything we needed for our short visit to town"
United States
Lauren W.
Norris Lake Cabin Getaway, Sleeps 6・View・Fire pit
A living room with a fireplace, a chandelier, and a large painting of flowers.

15. 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 NZ$959
includes taxes & fees
27 Oct - 28 Oct
Forget your worries in this spacious 5-Bedroom Home in Downtown Barbourville.
A spacious loft-style room with a high ceiling, large windows, a fireplace, and a cozy seating area.

16. 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 NZ$954
includes taxes & fees
3 Nov - 4 Nov
MOUNTAIN TOP CABIN WITH PARTNERING MARINA ON NORRIS LAKE
A wooden deck with wicker furniture, a view of a river, and a bridge in the distance.

17. 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, (50 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 NZ$1,296
includes taxes & fees
28 Oct - 29 Oct
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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Top Middlesboro Hotel Reviews

Pine Mountain State Resort Park

Pine Mountain State Resort Park

8/10 Good
"Beautiful scenery extremely helpful staff, coffee in dinning room was weak,food was just ok."
Charles 2-night trip
Posted 16 hours ago
Pine Mountain State Resort Park

Find out more about Middlesboro

Middlesboro Holiday Homes information

Number of reviews
247
Accommodation
173 Holiday Homes
Lowest Price
NZ$319
Highest Price
NZ$1,296