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
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Middlesboro vacation 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
9.0 out of 10, Wonderful, (6 reviews)
"We enjoyed our stay. "
United States
Emily S.
The price is CA $243
CA $504 total
includes taxes & fees
Jul 13 - Jul 14
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
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)
The price is CA $236
CA $495 total
includes taxes & fees
Jul 28 - Jul 29
Welcoming 3-bedroom house with AC in charming Middlesboro
Dining

Private bungalow close to LMU, ARH, Cumberland Gap

Private bungalow close to LMU, ARH, Cumberland Gap
Middlesboro
The price is CA $170
CA $407 total
includes taxes & fees
Aug 10 - Aug 11
Private bungalow close to LMU, ARH, Cumberland Gap
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 CA $268
CA $554 total
includes taxes & fees
Aug 6 - Aug 7
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
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)
"clean house very beautiful, host was amazing, scenery stunning. "
United States
Evelyn B.
The price is CA $249
CA $446 total
includes taxes & fees
Jul 13 - Jul 14
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
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 CA $125
CA $445 total
includes taxes & fees
Jul 13 - Jul 14
Peaceful & Private! Pet-Friendly Williamsburg Home
Exterior

Blissful Bungalow across from LMU campus

Blissful Bungalow across from LMU campus
Harrogate
9.6 out of 10, Exceptional, (39 reviews)
"Very convenient to everything we needed to do, very clean and neat"
United States
Brandi L.
The price is CA $196
CA $370 total
includes taxes & fees
Jul 12 - Jul 13
Blissful Bungalow across from LMU campus
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
9.2 out of 10, Wonderful, (23 reviews)
"Was in a great location to be able to go to multiple riding locations. "
United States
Sara R.
The price is CA $128
CA $255 total
includes taxes & fees
Jul 23 - Jul 24
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
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, (2 reviews)
"It was a nice clean place. The communication with the host was great, had no problems with anything at all. Will definitely book it again!!"
United States
Junior S.
The price is CA $185
CA $321 total
includes taxes & fees
Jul 19 - Jul 20
The Lodge Cabin ~Norris Lake Views and Mountain Backdrops
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 CA $213
CA $482 total
includes taxes & fees
Aug 2 - Aug 3
LMU Pine Mtn State Park Cumberland Gap Laurel Cove
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 CA $250
CA $462 total
includes taxes & fees
Aug 9 - Aug 10
Harrogate Home Mountain View’s Dog Friendly
TV

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, (30 reviews)
The price is CA $344
CA $786 total
includes taxes & fees
Jul 15 - Jul 16
MOUNTAIN TOP CABIN WITH PARTNERING MARINA ON NORRIS LAKE
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 CA $151
CA $381 total
includes taxes & fees
Jul 21 - Jul 22
Min. to Laurel Cove, LMU & Union, & Bell Theater
Fridge, microwave, oven, stovetop

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 $140
CA $657 total
includes taxes & fees
Aug 3 - Aug 4
Norris Lake Cabin Getaway, Sleeps 6・View・Fire pit
Outdoor dining

Lone Mountain View at Norris Lake!

Lone Mountain View at Norris Lake!
New Tazewell
The price is CA $507
CA $1,368 total
includes taxes & fees
Jul 21 - Jul 22
Lone Mountain View at Norris Lake!
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 CA $1,221
CA $2,116 total
includes taxes & fees
Aug 5 - Aug 6
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
"Nice property. The lodge rooms need updated. The on-site restaurant food and service was terrible was terrible."
Nicole 2-night trip
Posted 1 hour ago
Pine Mountain State Resort Park

Find out more about Middlesboro

Middlesboro Vacation Homes information

Number of reviews
141
Accommodation
185 Vacation Homes
Lowest Price
CA $255
Highest Price
CA $2,116

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