Holiday Homes in Middlesboro

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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

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, (23 reviews)
"Very nice and extra clean great time"
United States
Johnny C.
The price is NZ$380
includes taxes & fees
23 Feb - 24 Feb
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
Exterior

3-bedroom home away from home in Middesboro. A family friendly environment.

3-bedroom home away from home in Middesboro. A family friendly environment.
2.0 star property
Middlesboro
The price is NZ$275
includes taxes & fees
23 Feb - 24 Feb
3-bedroom home away from home in Middesboro. A family friendly environment.
Exterior detail

Welcoming 3-bedroom house with AC in charming Middlesboro

Welcoming 3-bedroom house with AC in charming Middlesboro
Middlesboro
The price is NZ$453
includes taxes & fees
26 Jan - 27 Jan
Welcoming 3-bedroom house with AC in charming Middlesboro
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
2.0 star property
Middlesboro
The price is NZ$466
includes taxes & fees
23 Feb - 24 Feb
3-bedroom bungalow in the heart of Crater City, near airport LMU & hiking trails
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 NZ$619
includes taxes & fees
23 Feb - 24 Feb
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 NZ$914
includes taxes & fees
5 Feb - 6 Feb
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, (31 reviews)
"visiting family at lmu, very close! We had a great weekend, would stay again! "
United States
Cherrish S.
The price is NZ$382
includes taxes & fees
28 Jan - 29 Jan
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 NZ$269
includes taxes & fees
28 Jan - 29 Jan
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
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 NZ$497
includes taxes & fees
24 Jan - 25 Jan
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Property grounds

Waterfront Retreat, Sleeps 14・Theater・Games・Grill

Waterfront Retreat, Sleeps 14・Theater・Games・Grill
2.0 star property
Maynardville
The price is NZ$787
includes taxes & fees
26 Jan - 27 Jan
Waterfront Retreat, Sleeps 14・Theater・Games・Grill
Property grounds

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

Tranquil Haven MTN Retreat, 3-bedroom, 2-bath, WIFI, AC in Beautiful Tazewell
2.0 star property
Tazewell
10.0 out of 10, Exceptional, (7 reviews)
"Great place that is well stocked and close to amenities as well. Spacious house with an awesome porch with a view!"
United States
Brendan W.
The price is NZ$735
includes taxes & fees
21 Feb - 22 Feb
Tranquil Haven MTN Retreat, 3-bedroom, 2-bath, WIFI, AC in Beautiful Tazewell
Terrace/patio

Lakefront Escape, Sleeps 10・Private Dock・Hot Tub

Lakefront Escape, Sleeps 10・Private Dock・Hot Tub
2.0 star property
Maynardville
The price is NZ$878
includes taxes & fees
26 Jan - 27 Jan
Lakefront Escape, Sleeps 10・Private Dock・Hot Tub
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 NZ$487
includes taxes & fees
24 Jan - 25 Jan
Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville
TV, DVD player, offices

Cozy Home, Sleeps 21・Views・Hot Tub・Large Yard

Cozy Home, Sleeps 21・Views・Hot Tub・Large Yard
New Tazewell
The price is NZ$1,183
includes taxes & fees
25 Jan - 26 Jan
Cozy Home, Sleeps 21・Views・Hot Tub・Large Yard
Property grounds

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

Lakefront Retreat, Sleeps 16・Dock・Boat Slips・Grill
2.0 star property
Rock Harbor
The price is NZ$1,123
includes taxes & fees
2 Feb - 3 Feb
Lakefront Retreat, Sleeps 16・Dock・Boat Slips・Grill
Outdoor dining

Jackson MTN Retreat 3-bedroom entire HOME in Harrogate-Near LMU & Bowling alley

Jackson MTN Retreat 3-bedroom entire HOME in Harrogate-Near LMU & Bowling alley
2.0 star property
Harrogate
The price is NZ$764
includes taxes & fees
26 Jan - 27 Jan
Jackson MTN Retreat 3-bedroom entire HOME in Harrogate-Near LMU & Bowling alley
Property grounds

Stunning Lakeview Home・Game Room・Dock・Hot Tub

Stunning Lakeview Home・Game Room・Dock・Hot Tub
Lakeside Estates
The price is NZ$2,081
includes taxes & fees
26 Jan - 27 Jan
Stunning Lakeview Home・Game Room・Dock・Hot Tub
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 NZ$355
includes taxes & fees
1 Feb - 2 Feb
3-Bedroom Cottage, Peaceful setting, Close to Parks, 2 min. from Bell Theatre
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
"The staff was excellent. They are wonderful people. They made sure everything was perfect. We enjoyed having breakfast with the other guests. They addressed any allergy concerns and tailored your breakfast for all. I would recommend this bed and breakfast it is the best one we have ever stayed at"
Paul 3-night trip
Posted 4 days ago
The Olde Mill Inn Bed & Breakfast

Find out more about Middlesboro

Middlesboro Holiday Homes information

Number of reviews
135
Accommodation
173 Holiday Homes
Lowest Price
NZ$269
Highest Price
NZ$1,191