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Check prices for these dates

In two weeks
May 8 - May 10
In two months
Jun 19 - Jun 21
In three months
Jul 17 - Jul 19
In four months
Aug 14 - Aug 16

Our top choices for Middlesboro vacation homes

3 bedrooms, desk, iron/ironing board, travel crib

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 ￥27,242
￥52,139 total
includes taxes & fees
May 12 - May 13
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 ￥18,675
￥42,890 total
includes taxes & fees
May 4 - May 5
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
10.0 out of 10, Exceptional, (1 review)
"Clean"
United States
Phineas S.
The price is ￥30,522
￥59,436 total
includes taxes & fees
May 21 - May 22
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
Exterior

Welcoming 3-bedroom house with AC in charming Middlesboro

Welcoming 3-bedroom house with AC in charming Middlesboro
Middlesboro
The price is ￥26,453
￥52,321 total
includes taxes & fees
May 19 - May 20
Welcoming 3-bedroom house with AC in charming Middlesboro
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, (20 reviews)
"Cute and cozy! Perfect place for us to use as a home base while in town visiting family. Lots of attention to the details, kitchen facilities are up to date and super clean. Already looking forward to booking again!"
United States
Lynette M.
The price is ￥12,850
￥26,917 total
includes taxes & fees
Apr 22 - Apr 23
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, (34 reviews)
"Very convenient to everything we needed to do, very clean and neat"
United States
Brandi L.
The price is ￥17,292
￥34,869 total
includes taxes & fees
Apr 22 - Apr 23
Blissful Bungalow across from LMU campus
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, (3 reviews)
"clean house very beautiful, host was amazing, scenery stunning. "
United States
Evelyn B.
The price is ￥20,560
￥40,680 total
includes taxes & fees
Apr 23 - Apr 24
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Private kitchen

3-Bedroom Cottage, Peaceful setting, Close to Parks, 2 min. from Bell Theatre

3-Bedroom Cottage, Peaceful setting, Close to Parks, 2 min. from Bell Theatre
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 ￥16,962
￥40,939 total
includes taxes & fees
Apr 22 - Apr 23
3-Bedroom Cottage, Peaceful setting, Close to Parks, 2 min. from Bell Theatre
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, (25 reviews)
"Great location for family gathering near local relatives. Beautiful views and close to New Tazewell. "
United States
Pamela D.
The price is ￥40,136
￥89,930 total
includes taxes & fees
May 19 - May 20
MOUNTAIN TOP CABIN WITH PARTNERING MARINA ON NORRIS LAKE
Terrace/patio

Peaceful & Private! Pet-Friendly Williamsburg Home

Peaceful & Private! Pet-Friendly Williamsburg Home
Williamsburg
10.0 out of 10, Exceptional, (1 review)
"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 ￥13,960
￥48,036 total
includes taxes & fees
Apr 22 - Apr 23
Peaceful & Private! Pet-Friendly Williamsburg Home
TV, fireplace, books

Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg

Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg
Williamsburg
The price is ￥14,766
￥54,203 total
includes taxes & fees
Apr 22 - Apr 23
Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg
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 ￥25,700
￥52,363 total
includes taxes & fees
Apr 22 - Apr 23
LMU Pine Mtn State Park Cumberland Gap Laurel Cove
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, (46 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 ￥36,341
￥112,006 total
includes taxes & fees
Apr 22 - Apr 23
Lake Front ★ No Wake w/ Dock ★ Gameroom ★ Carved FirePit ★ 2nd House Available
Property grounds

Entire Home -Tranquil Haven MTN Retreat, 3-bedroom, 2-bath, WIFI, AC in Tazewell

Entire Home -Tranquil Haven MTN Retreat, 3-bedroom, 2-bath, WIFI, AC in Tazewell
Tazewell
10.0 out of 10, Exceptional, (8 reviews)
"Perfect location!! House was immaculate. Good job with the hostess book it helped a lot with the details of the surrounding area. Beautiful Home. Would stay again if we travel into the area."
United States
Jim A.
The price is ￥26,652
￥63,609 total
includes taxes & fees
Apr 27 - Apr 28
Entire Home -Tranquil Haven MTN Retreat, 3-bedroom, 2-bath, WIFI, AC in Tazewell
Outdoor dining

Entire Home - Jackson MTN Retreat 3-bedroom 2 Bath -Near LMU & Bowling alley

Entire Home - Jackson MTN Retreat 3-bedroom 2 Bath -Near LMU & Bowling alley
Harrogate
10.0 out of 10, Exceptional, (3 reviews)
"Clean. Good location for our purposes, quiet neighborhood with a nice view and dark sky. Very strange layout, with the twin trundle and king in the same converted garage, and other 2 bedrooms separated by a set of glass doors and a curtain. The house was missing trash bags and extra toilet paper upon arrival but Dollar General was a hop and skip away. Otherwise equipped fine. Easy in and out. "
United States
William D.
The price is ￥26,673
￥65,997 total
includes taxes & fees
Apr 27 - Apr 28
Entire Home - Jackson MTN Retreat 3-bedroom 2 Bath -Near LMU & Bowling alley
Property grounds

Waterfront Retreat, Sleeps 14, Theater, Games, Grill

Waterfront Retreat, Sleeps 14, Theater, Games, Grill
Maynardville
The price is ￥22,368
￥78,761 total
includes taxes & fees
Apr 29 - Apr 30
Waterfront Retreat, Sleeps 14, Theater, Games, Grill
Interior

Mountain-View Suite Near I-75 EV Charging

Mountain-View Suite Near I-75 EV Charging
Jellico
The price is ￥19,037
￥42,459 total
includes taxes & fees
Apr 29 - Apr 30
Mountain-View Suite Near I-75 EV Charging
Outdoor dining

Lakefront Home w/Private Dock, Hot Tub & Sleeps 22

Lakefront Home w/Private Dock, Hot Tub & Sleeps 22
Lakeside Estates
The price is ￥72,657
￥212,143 total
includes taxes & fees
May 3 - May 4
Lakefront Home w/Private Dock, Hot Tub & Sleeps 22
Terrace/patio

Lakefront Escape, Sleeps 10, Private Dock, Hot Tub

Lakefront Escape, Sleeps 10, Private Dock, Hot Tub
Maynardville
10.0 out of 10, Exceptional, (1 review)
"Cabin was really nice"
United States
RYAN M.
The price is ￥25,700
￥86,310 total
includes taxes & fees
May 6 - May 7
Lakefront Escape, Sleeps 10, Private Dock, Hot Tub
Property grounds

Lakefront Retreat, Sleeps 16, Dock, Boat Slips, Grill

Lakefront Retreat, Sleeps 16, Dock, Boat Slips, Grill
Rock Harbor
The price is ￥45,212
￥131,249 total
includes taxes & fees
Apr 29 - Apr 30
Lakefront Retreat, Sleeps 16, Dock, Boat Slips, Grill
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

10/10 Excellent
"Super clean and everyone was super nice. The view out the front door was so gorgeous."
Karen 2-night trip
Posted 4 hours ago
Sleep Inn & Suites Middlesboro

Find out more about Middlesboro

Middlesboro Vacation Homes information

Number of reviews
109
Accommodation
179 Vacation Homes
Lowest Price
￥26,917
Highest Price
￥212,143