Holiday Homes in Middlesboro

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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 June - 28 June

Our top choices for Middlesboro holiday homes

2 bedrooms, iron/ironing board, free WiFi, bed sheets

4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,

4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
Middlesboro
10.0 out of 10, Exceptional, (26 reviews)
"Very nice and extra clean great time"
United States
Johnny C.
The price is AU$325
includes taxes & fees
9 Mar - 10 Mar
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
Exterior

3-bedroom bungalow in the heart of Crater City, near airport LMU & hiking trails

3-bedroom bungalow in the heart of Crater City, near airport LMU & hiking trails
Middlesboro
The price is AU$402
includes taxes & fees
6 Mar - 7 Mar
3-bedroom bungalow in the heart of Crater City, near airport LMU & hiking trails
Exterior detail

Welcoming 3-bedroom house with AC in charming Middlesboro

Welcoming 3-bedroom house with AC in charming Middlesboro
Middlesboro
The price is AU$592
includes taxes & fees
2 Apr - 3 Apr
Welcoming 3-bedroom house with AC in charming Middlesboro
3 bedrooms, desk, iron/ironing board, travel cot

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 AU$521
includes taxes & fees
9 Mar - 10 Mar
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Microwave, oven, stovetop

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 AU$533
includes taxes & fees
2 Apr - 3 Apr
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
Exterior

Blissful Bungalow across from LMU campus

Blissful Bungalow across from LMU campus
Harrogate
9.6 out of 10, Exceptional, (33 reviews)
"Cozy feel and relaxing. "
United States
Cynthia
The price is AU$317
includes taxes & fees
8 Mar - 9 Mar
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
9.4 out of 10, Exceptional, (19 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 AU$227
includes taxes & fees
5 Mar - 6 Mar
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
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, (23 reviews)
"Great location with friendly neighbors!"
United States
Evan C.
The price is AU$424
includes taxes & fees
8 Mar - 9 Mar
Harrogate Home Mountain View’s Dog Friendly
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, (2 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 AU$362
includes taxes & fees
10 Mar - 11 Mar
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Property grounds

Lakefront, minimal steps to water. Large private dock, Chef's kitchen

Lakefront, minimal steps to water. Large private dock, Chef's kitchen
Speedwell
10.0 out of 10, Exceptional, (16 reviews)
"Lovely home, great location in a quiet cove. Definitely intend to come back."
United States
Jeri M.
The price is AU$1,497
includes taxes & fees
5 Mar - 6 Mar
Lakefront, minimal steps to water. Large private dock, Chef's kitchen
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 AU$727
includes taxes & fees
12 Mar - 13 Mar
Lakefront Escape, Sleeps 10・Private Dock・Hot Tub
Property grounds

Waterfront Retreat, Sleeps 14・Theater・Games・Grill

Waterfront Retreat, Sleeps 14・Theater・Games・Grill
Maynardville
The price is AU$661
includes taxes & fees
5 Mar - 6 Mar
Waterfront Retreat, Sleeps 14・Theater・Games・Grill
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, (7 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 AU$561
includes taxes & fees
5 Mar - 6 Mar
Entire Home -Tranquil Haven MTN Retreat, 3-bedroom, 2-bath, WIFI, AC in Tazewell
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 AU$915
includes taxes & fees
20 Mar - 21 Mar
MOUNTAIN TOP CABIN WITH PARTNERING MARINA ON NORRIS LAKE
Exterior

Cozy A Frame Cabin, Sleep 8・Near Marina・Deck・Grill

Cozy A Frame Cabin, Sleep 8・Near Marina・Deck・Grill
Flat Hollow Marina
The price is AU$475
includes taxes & fees
31 Mar - 1 Apr
Cozy A Frame Cabin, Sleep 8・Near Marina・Deck・Grill
Terrace/patio

Peaceful & Private! Pet-Friendly Williamsburg Home

Peaceful & Private! Pet-Friendly Williamsburg Home
Williamsburg
The price is AU$428
includes taxes & fees
13 Mar - 14 Mar
Peaceful & Private! Pet-Friendly Williamsburg Home
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 AU$989
includes taxes & fees
15 Mar - 16 Mar
Lake Front ★ No Wake w/ Dock ★ Gameroom ★ Carved FirePit ★ 2nd House Available
Private kitchen

Luxury Group and Family Cabin w/ Lake Views

Luxury Group and Family Cabin w/ Lake Views
New Tazewell
The price is AU$901
includes taxes & fees
5 Mar - 6 Mar
Luxury Group and Family Cabin w/ Lake Views
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
The price is AU$570
includes taxes & fees
9 Mar - 10 Mar
Entire Home - Jackson MTN Retreat 3-bedroom 2 Bath -Near LMU & Bowling alley
Living area

Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville

Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville
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 AU$458
includes taxes & fees
5 Mar - 6 Mar
Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville
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

The Olde Mill Inn Bed & Breakfast

The Olde Mill Inn Bed & Breakfast

10/10 Excellent
"We enjoyed this cozy bed and breakfast. It's a great location - so beautiful! The staff was amazing - we had a meeting at LMU and were missing breakfast. So they packed us a breakfast and put it in the common area refrigerator for us to grab in the morning. It was also handy to fill our cups with ice water. "
Kim 2-night trip
Posted 2 days ago
The Olde Mill Inn Bed & Breakfast

Find out more about Middlesboro

Middlesboro Holiday Homes information

Number of reviews
205
Accommodation
166 Holiday Homes
Lowest Price
AU$227
Highest Price
AU$1,497