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Holiday Homes in Middlesboro

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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 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 €305
includes taxes & fees
15 Jun - 16 Jun
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 €242
includes taxes & fees
15 Jun - 16 Jun
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 €299
includes taxes & fees
16 Jun - 17 Jun
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)
"Clean"
United States
Phineas S.
The price is €356
includes taxes & fees
23 Jun - 24 Jun
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
TV, fireplace, books

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 €300
includes taxes & fees
15 Jun - 16 Jun
Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg
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 €151
includes taxes & fees
21 Jun - 22 Jun
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
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 €194
includes taxes & fees
15 Jun - 16 Jun
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 €266
includes taxes & fees
15 Jun - 16 Jun
Peaceful & Private! Pet-Friendly Williamsburg Home
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, (7 reviews)
"We stayed here for a wedding weekend in Pineville, KY, and it was absolutely perfect from start to finish. The home was spotless, cozy, and had everything we could possibly need. The beds were so comfortable, and we instantly felt at home the moment we walked in.What truly set this stay apart was the host’s kindness and above-and-beyond hospitality. We got lost in the middle of the night trying to find the property, and the host stayed on the phone with us, patiently guiding us right to the...
United States
Samantha P.
The price is €232
includes taxes & fees
15 Jun - 16 Jun
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 €258
includes taxes & fees
15 Jun - 16 Jun
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 €224
includes taxes & fees
6 Jul - 7 Jul
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 €306
includes taxes & fees
15 Jun - 16 Jun
LMU Pine Mtn State Park Cumberland Gap Laurel Cove
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, (26 reviews)
"Great location for family gathering near local relatives. Beautiful views and close to New Tazewell. "
United States
Pamela D.
The price is €496
includes taxes & fees
17 Jun - 18 Jun
MOUNTAIN TOP CABIN WITH PARTNERING MARINA ON 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 €1,389
includes taxes & fees
30 Jun - 1 Jul
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

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

8/10 Good
"Check in was easy, room was clean and spacious and breakfast was a typical hotel breakfast"
JOANNE 1-night trip
Posted 9 hours ago
Sleep Inn & Suites Middlesboro

Find out more about Middlesboro

Middlesboro Holiday Homes information

Number of reviews
132
Accommodation
178 Holiday Homes
Lowest Price
€151
Highest Price
€1,389