Photo by Alexis Wyrick

Search Vacation Homes in Middlesboro

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Dec 12 - Dec 14
In two months
Jan 23 - Jan 25
In three months
Feb 20 - Feb 22
In four months
Mar 20 - Mar 22

Vacation Homes in Middlesboro

2 bedrooms, iron/ironing board, free WiFi, bed sheets
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,

Vacation Home in Middlesboro

10.0 out of 10, Exceptional, (22)
"Great property! Very clean and homey!"
United States
Lillian I.
The price is ￥18,585
￥35,812 total
includes taxes & fees
Dec 1 - Dec 2
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
3 bedrooms, desk, iron/ironing board, travel crib
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

Vacation Home in Middlesboro

9.2 out of 10, Wonderful, (5)
"We enjoyed our stay. "
United States
Emily S.
The price is ￥27,332
￥58,023 total
includes taxes & fees
Dec 7 - Dec 8
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

Vacation Home in Middlesboro

10.0 out of 10, Exceptional, (1)
"Clean"
United States
Phineas S.
The price is ￥30,767
￥58,366 total
includes taxes & fees
Dec 9 - Dec 10
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
Property grounds
Welcoming 3-bedroom house with AC in charming Middlesboro

Vacation Home in Middlesboro

The price is ￥20,944
￥41,166 total
includes taxes & fees
Dec 1 - Dec 2
Welcoming 3-bedroom house with AC in charming Middlesboro
Terrace/patio
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina

Vacation Home in Speedwell

9.4 out of 10, Exceptional, (19)
"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 ￥10,542
￥24,091 total
includes taxes & fees
Dec 10 - Dec 11
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
Terrace/patio
Peaceful & Private! Pet-Friendly Williamsburg Home

Vacation Home in Williamsburg

2.0 star property
The price is ￥13,744
￥47,637 total
includes taxes & fees
Dec 11 - Dec 12
Peaceful & Private! Pet-Friendly Williamsburg Home
Fridge, microwave, oven, stovetop
Harrogate Home Mountain View’s Dog Friendly

Vacation Home in Harrogate

10.0 out of 10, Exceptional, (22)
"Great location with friendly neighbors!"
United States
Evan C.
The price is ￥24,598
￥46,899 total
includes taxes & fees
Dec 1 - Dec 2
Harrogate Home Mountain View’s Dog Friendly
Property grounds
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky

Vacation Home in Pineville

10.0 out of 10, Exceptional, (2)
"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 ￥22,349
￥42,887 total
includes taxes & fees
Dec 1 - Dec 2
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Fridge, microwave, oven, stovetop
Tranquil Haven MTN Retreat, 3-bedroom, 2-bath, WIFI, AC in Beautiful Tazewell

Vacation Home in Tazewell

2.0 star property
10.0 out of 10, Exceptional, (6)
"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 ￥31,080
￥68,212 total
includes taxes & fees
Dec 14 - Dec 15
Tranquil Haven MTN Retreat, 3-bedroom, 2-bath, WIFI, AC in Beautiful Tazewell
Living area
Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville

Vacation Home in Pineville

10.0 out of 10, Exceptional, (1)
"Well cared for property with nice upgrades! Perfect for our stay, everything we needed, and accommodating. "
United States
Hope C.
The price is ￥23,896
￥34,608 total
includes taxes & fees
Dec 2 - Dec 3
Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville
Private kitchen
3-Bedroom Cottage, Peaceful setting, Close to Parks, 2 min. from Bell Theatre

Vacation Home in Pineville

4.8 out of 10, (3)
"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 ￥10,776
￥32,711 total
includes taxes & fees
Dec 1 - Dec 2
3-Bedroom Cottage, Peaceful setting, Close to Parks, 2 min. from Bell Theatre
Property grounds
Lake Front ★ No Wake w/ Dock ★ Gameroom ★ Carved FirePit ★ 2nd House Available

Vacation Home in LaFollette

10.0 out of 10, Exceptional, (46)
"Very nice house. Great location. Easy check in."
United States
Vicki R.
The price is ￥34,222
￥109,273 total
includes taxes & fees
Dec 1 - Dec 2
Lake Front ★ No Wake w/ Dock ★ Gameroom ★ Carved FirePit ★ 2nd House Available
Exterior
Jackson MTN Retreat 3-bedroom entire HOME in Harrogate-Near LMU & Bowling alley

Vacation Home in Harrogate

2.0 star property
The price is ￥31,080
￥71,173 total
includes taxes & fees
Dec 1 - Dec 2
Jackson MTN Retreat 3-bedroom entire HOME in Harrogate-Near LMU & Bowling alley
Comfort House | Private kitchen | Full-size fridge, microwave, oven, stovetop
The House on Park Avenue

Vacation Home in Pineville

3.5 star property
The price is ￥45,416
￥62,404 total
includes taxes & fees
Dec 1 - Dec 2
The House on Park Avenue
Fridge, microwave, oven, stovetop
Lakeview Home/Private Boat Dock/Hot tub/Golf Cart/Gameroom/Stunning Fall Views

Vacation Home in Lakeside Estates

9.0 out of 10, Wonderful, (22)
"The house was beautiful! The path to the dock was definitely steep but it didn’t bother us much, and the double decker dock was great! The kids as well as adults loved jumping and sliding!"
United States
jackie m.
The price is ￥105,422
￥251,894 total
includes taxes & fees
Dec 27 - Dec 28
Lakeview Home/Private Boat Dock/Hot tub/Golf Cart/Gameroom/Stunning Fall Views
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middlesboro Hotel Reviews

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

10/10 Excellent
"Clean environment, friendly staff "
Shannon 1-night trip
Posted 5 days ago
Sleep Inn & Suites Middlesboro

Find out more about Middlesboro

Middlesboro Vacation Homes information

Number of reviews
142
Accommodation
146 Vacation Homes
Lowest Price
￥24,091
Highest Price
￥251,894

Explore a world of travel with Expedia