Search Vacation Homes in Middlesboro

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Middlesboro vacation homes

10.0 out of 10, Exceptional, (23 reviews)
"Very nice and extra clean great time"
United States
Johnny C.
The price is ¥18,856
¥35,983 total
includes taxes & fees
Jan 20 - Jan 21
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
The price is ¥16,225
¥25,746 total
includes taxes & fees
Feb 1 - Feb 2
3-bedroom home away from home in Middesboro. A family friendly environment.
9.2 out of 10, Wonderful, (5 reviews)
"We enjoyed our stay. "
United States
Emily S.
The price is ¥27,729
¥58,866 total
includes taxes & fees
Jan 18 - Jan 19
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
The price is ¥21,248
¥42,637 total
includes taxes & fees
Jan 26 - Jan 27
Welcoming 3-bedroom house with AC in charming Middlesboro
10.0 out of 10, Exceptional, (1 review)
"Clean"
United States
Phineas S.
The price is ¥52,621
¥85,433 total
includes taxes & fees
Jan 16 - Jan 17
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
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 ¥11,408
¥25,255 total
includes taxes & fees
Jan 18 - Jan 19
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
9.6 out of 10, Exceptional, (30 reviews)
"visiting family at lmu, very close! We had a great weekend, would stay again! "
United States
Cherrish S.
The price is ¥17,271
¥35,144 total
includes taxes & fees
Jan 27 - Jan 28
Blissful Bungalow across from LMU campus
2.0 star property
The price is ¥13,944
¥48,854 total
includes taxes & fees
Jan 16 - Jan 17
Peaceful & Private! Pet-Friendly Williamsburg Home
10.0 out of 10, Exceptional, (22 reviews)
"Great location with friendly neighbors!"
United States
Evan C.
The price is ¥24,956
¥47,581 total
includes taxes & fees
Jan 18 - Jan 19
Harrogate Home Mountain View’s Dog Friendly
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 ¥25,241
¥46,516 total
includes taxes & fees
Jan 16 - Jan 17
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
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 ¥31,532
¥69,203 total
includes taxes & fees
Jan 16 - Jan 17
Tranquil Haven MTN Retreat, 3-bedroom, 2-bath, WIFI, AC in Beautiful Tazewell
2.0 star property
The price is ¥19,014
¥73,240 total
includes taxes & fees
Jan 18 - Jan 19
Waterfront Retreat, Sleeps 14・Theater・Games・Grill
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 ¥26,952
¥45,608 total
includes taxes & fees
Jan 16 - Jan 17
Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville
2.0 star property
The price is ¥22,025
¥81,981 total
includes taxes & fees
Jan 18 - Jan 19
Lakefront Escape, Sleeps 10・Private Dock・Hot Tub
2.0 star property
The price is ¥23,768
¥112,102 total
includes taxes & fees
Jan 18 - Jan 19
Cozy Home, Sleeps 21・Views・Hot Tub・Large Yard
2.0 star property
Lakefront Retreat, Sleeps 16・Dock・Boat Slips・Grill
The price is ¥31,532
¥71,415 total
includes taxes & fees
Jan 19 - Jan 20
Jackson MTN Retreat 3-bedroom entire HOME in Harrogate-Near LMU & Bowling alley
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 ¥36,298
¥112,823 total
includes taxes & fees
Jan 21 - Jan 22
Lake Front ★ No Wake w/ Dock ★ Gameroom ★ Carved FirePit ★ 2nd House Available
2.0 star property
The price is ¥48,327
¥116,210 total
includes taxes & fees
Jan 19 - Jan 20
Cozy Lakefront Home, Sleep 12・Private Dock・Hot Tub
The price is ¥71,303
¥198,326 total
includes taxes & fees
Jan 18 - Jan 19
Stunning Lakeview Home・Game Room・Dock・Hot Tub
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Middlesboro Hotel Reviews

Find out more about Middlesboro

Middlesboro Vacation Homes information

Number of reviews
153
Accommodation
173 Vacation Homes
Lowest Price
¥25,255
Highest Price
¥112,823