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

Middlesboro Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Middlesboro vacation homes

A dining area with a table set for four, a ceiling fan, and a sign above reading 'BE OUR GUEST'.

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

Private bungalow close to LMU, ARH, Cumberland Gap
Middlesboro
The price is CA $216
CA $466 total
includes taxes & fees
Sep 12 - Sep 13
Private bungalow close to LMU, ARH, Cumberland Gap
A bedroom with a bed, pillows, a nightstand, a lamp, a window with blinds, and a kitchen area with a refrigerator.

2. 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, (7 reviews)
"We enjoyed our stay. "
United States
Emily S.
The price is CA $282
CA $548 total
includes taxes & fees
Sep 22 - Sep 23
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.

3. 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 CA $278
CA $542 total
includes taxes & fees
Sep 21 - Sep 22
Welcoming 3-bedroom house with AC in charming Middlesboro
A living room with a TV on a wooden stand, a white chair, a small table, and a sofa.

4. 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 CA $299
CA $590 total
includes taxes & fees
Sep 15 - Sep 16
House close to ARH Hospital, Tackett Creek & LMU!
An aerial view of a campus with multiple buildings, a central tower, and a large open grassy area.

5. Blissful Bungalow across from LMU campus

Blissful Bungalow across from LMU campus
Harrogate
9.6 out of 10, Exceptional, (42 reviews)
"Very convenient to everything we needed to do, very clean and neat"
United States
Brandi L.
The price is CA $152
CA $309 total
includes taxes & fees
Sep 12 - Sep 13
Blissful Bungalow across from LMU campus
A wooden deck with a railing, a brick building, and a door with a window.

6. 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, (11 reviews)
"Beautiful house. Great stay"
United States
Kevin S.
The price is CA $220
CA $405 total
includes taxes & fees
Sep 12 - Sep 13
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
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, (28 reviews)
"Great place to stay. "
United States
Jodi D.
The price is CA $205
CA $400 total
includes taxes & fees
Sep 14 - Sep 15
Harrogate Home Mountain View’s Dog Friendly
A covered outdoor deck with wooden flooring and metal chairs.

8. 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 CA $121
CA $434 total
includes taxes & fees
Sep 12 - Sep 13
Peaceful & Private! Pet-Friendly Williamsburg Home
A two-story house with a front porch, a blue door, and a small garden area with potted plants.

9. 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 CA $148
CA $372 total
includes taxes & fees
Sep 15 - Sep 16
Min. to Laurel Cove, LMU & Union, & Bell Theater
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 CA $128
CA $482 total
includes taxes & fees
Sep 12 - Sep 13
Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg
An outdoor patio with a fire pit, surrounded by chairs and a pergola with string lights.

11. 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, (26 reviews)
"The property was ideal. It was affordable, not too remote and had everything we needed."
United States
Julie R.
The price is CA $112
CA $234 total
includes taxes & fees
Sep 20 - Sep 21
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.

12. 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.
The price is CA $137
CA $675 total
includes taxes & fees
Oct 6 - Oct 7
Norris Lake Cabin Getaway, Sleeps 6・View・Fire pit
A spacious loft-style room with a high ceiling, large windows, a fireplace, and a cozy seating area.

13. 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, (31 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 CA $371
CA $810 total
includes taxes & fees
Sep 16 - Sep 17
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.

14. 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, (49 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 CA $333
CA $1,004 total
includes taxes & fees
Sep 23 - Sep 24
Lake Front ★ No Wake w/ Dock ★ Gameroom ★ Carved FirePit ★ 2nd House Available
A wooden deck leading to a dock over a calm lake, surrounded by trees with autumn foliage.

15. Norris Lake Cabin – Game Room, Dock & Stunning Views

Norris Lake Cabin – Game Room, Dock & Stunning Views
New Tazewell
9.8 out of 10, Exceptional, (18 reviews)
"Awesome place to stay. Friendly owners. Lake is beautiful. Would stay here again "
United States
Taryn T.
The price is CA $567
CA $1,197 total
includes taxes & fees
Sep 21 - Sep 22
Norris Lake Cabin – Game Room, Dock & Stunning Views
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

10/10 Excellent
"Loved the whole place"
James 2-night trip
Posted 1 day ago
Pine Mountain State Resort Park

Find out more about Middlesboro

Middlesboro Vacation Homes information

Number of reviews
2,545
Accommodation
173 Vacation Homes
Lowest Price
CA $86
Highest Price
CA $471

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