Photo by Alexis Wyrick

Holiday 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

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

Featured Holiday 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,
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
10.0 out of 10, Exceptional, (19)
"Our group had a wonderful time staying at Uncle Ernie's! Everything was neat, tidy, and felt like home. We definitely will be back next time we are in the area!"
United States
Savannah P.
The price is NZ$404
includes taxes & fees
10 Nov - 11 Nov
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
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.
9.2 out of 10, Wonderful, (5)
"We enjoyed our stay. "
United States
Emily S.
The price is NZ$630
includes taxes & fees
19 Nov - 20 Nov
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Exterior detail
Welcoming 3-bedroom house with AC in charming Middlesboro
Welcoming 3-bedroom house with AC in charming Middlesboro
The price is NZ$426
includes taxes & fees
2 Nov - 3 Nov
Welcoming 3-bedroom house with AC in charming Middlesboro
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
The price is NZ$945
includes taxes & fees
26 Oct - 27 Oct
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
Outdoor dining
Comfy A-frame cabin with deck, gas grill, Internet, close to marina
Comfy A-frame cabin with deck, gas grill, Internet, close to marina
2.0 star property
10.0 out of 10, Exceptional, (5)
"Perfect for a family getaway on the lake!"
United States
Angel S.
The price is NZ$595
includes taxes & fees
27 Oct - 28 Oct
Comfy A-frame cabin with deck, gas grill, Internet, close to marina
Outdoor dining
Cozy A-frame home with fire pit, deck, pickleball court, and covered boat slip
Cozy A-frame home with fire pit, deck, pickleball court, and covered boat slip
2.0 star property
9.8 out of 10, Exceptional, (8)
"This cabin is a perfect mixture of lake and privacy. Also there is plenty of room outside for the little ones to play in the giant concrete pad. With only very short ride down the hill to the marina it is a great spot to get away from the noise but be very close for convenience! Will definitely stay again thanks so much !!!"
United States
Joshua N.
The price is NZ$595
includes taxes & fees
27 Oct - 28 Oct
Cozy A-frame home with fire pit, deck, pickleball court, and covered boat slip
Fridge, microwave, oven, stovetop
Harrogate Home Mountain View’s Dog Friendly
Harrogate Home Mountain View’s Dog Friendly
9.8 out of 10, Exceptional, (20)
"Good space for me, my family, and my dogs to crash while we did a quick visit to the Gap."
United States
Lisa F.
The price is NZ$522
includes taxes & fees
27 Oct - 28 Oct
Harrogate Home Mountain View’s Dog Friendly
Terrace/patio
Peaceful & Private! Pet-Friendly Williamsburg Home
Peaceful & Private! Pet-Friendly Williamsburg Home
2.0 star property
The price is NZ$544
includes taxes & fees
26 Oct - 27 Oct
Peaceful & Private! Pet-Friendly Williamsburg Home
Property grounds
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
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 NZ$514
includes taxes & fees
26 Oct - 27 Oct
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Fridge, microwave, oven, stovetop
Lovely lakefront home with fire pit, fireplace, dock and gas grill
Lovely lakefront home with fire pit, fireplace, dock and gas grill
2.0 star property
10.0 out of 10, Exceptional, (17)
"Perfect lake get away"
United States
Rita W.
The price is NZ$1,162
includes taxes & fees
6 Nov - 7 Nov
Lovely lakefront home with fire pit, fireplace, dock and gas grill
Exterior
1928 Home in the heart of Cumberland Gap
1928 Home in the heart of Cumberland Gap
9.8 out of 10, Exceptional, (91)
"The host was easy to reach and the house was clean. Cumberland Gap has really nice trails to walk, and lots of antique stores. Shout out to the restaurant just down the street "1919" Great food We would definetly stay again."
United States
Edith G.
The price is NZ$400
includes taxes & fees
3 Nov - 4 Nov
1928 Home in the heart of Cumberland Gap
Terrace/patio
Located just a short 5-minute walk to springs dock and resort
Located just a short 5-minute walk to springs dock and resort
2.0 star property
9.4 out of 10, Exceptional, (6)
"We really enjoyed our stay. House is laid out nice and has a well equipped kitchen. The driveway is steep which is typical for the area. We walked down to the marina to our boat daily. We would stay again."
United States
Holli Y.
The price is NZ$877
includes taxes & fees
27 Oct - 28 Oct
Located just a short 5-minute walk to springs dock and resort
Dining
Rustic lakeside home with private dock, firepit, grill, smoker, and mtn views
Rustic lakeside home with private dock, firepit, grill, smoker, and mtn views
9.8 out of 10, Exceptional, (8)
"We had such a wonderful week at this gorgeous lake house in a beautiful location."
United States
Ashley R.
Rustic lakeside home with private dock, firepit, grill, smoker, and mtn views
Fridge, microwave, oven, stovetop
Dog-friendly lakefront house with hot tub, central AC, & mountain view
Dog-friendly lakefront house with hot tub, central AC, & mountain view
9.6 out of 10, Exceptional, (17)
"Lovely view and beautiful lake."
United States
Lisa M.
Dog-friendly lakefront house with hot tub, central AC, & mountain view
Interior
Waterfront living with private dock, private boat launch, kayaks & firepit
Waterfront living with private dock, private boat launch, kayaks & firepit
10.0 out of 10, Exceptional, (10)
"The house was perfect and literally steps down the driveway to its own private dock. Will stay here again!"
United States
Aubree F.
The price is NZ$1,132
includes taxes & fees
26 Oct - 27 Oct
Waterfront living with private dock, private boat launch, kayaks & firepit
Fridge, microwave, oven, stovetop
Lake Escape at Powell Valley Marina
Lake Escape at Powell Valley Marina
9.8 out of 10, Exceptional, (7)
"We were looking for easy access to Powell Valley Marina for our family. Very clean, really decorated nicely, just a little smaller than we expected but it worked for our 4 family members. I would definitely stay there again! We took our golf cart and could access the marina quickly!! "
United States
Cathy Y.
Lake Escape at Powell Valley Marina
Property grounds
Lake Front ★ No Wake w/ Dock ★ Gameroom ★ Carved FirePit ★ 2nd House Available
Lake Front ★ No Wake w/ Dock ★ Gameroom ★ Carved FirePit ★ 2nd House Available
10.0 out of 10, Exceptional, (45)
"The house was beautiful and had everything we needed. The owner was very responsive to all my questions. The kids loved the game room and ping pong table."
United States
Jamie W.
The price is NZ$1,217
includes taxes & fees
26 Oct - 27 Oct
Lake Front ★ No Wake w/ Dock ★ Gameroom ★ Carved FirePit ★ 2nd House Available
Dining
Cozy home with stunning views, fire pit, and large fenced in yard
Cozy home with stunning views, fire pit, and large fenced in yard
2.0 star property
10.0 out of 10, Exceptional, (4)
"Beautiful property, well maintained"
United States
Jesus V.
The price is NZ$1,260
includes taxes & fees
26 Oct - 27 Oct
Cozy home with stunning views, fire pit, and large fenced in yard
Property grounds
Waterfront home with game room, theater, deck, dock & fireplace
Waterfront home with game room, theater, deck, dock & fireplace
10.0 out of 10, Exceptional, (49)
"Family trip to Norris Lake...great house had everything we needed."
United States
Suzanne K.
The price is NZ$1,157
includes taxes & fees
27 Oct - 28 Oct
Waterfront home with game room, theater, deck, dock & fireplace
Terrace/patio
Beautiful lakefront house with full kitchen, private dock, & hot tub
Beautiful lakefront house with full kitchen, private dock, & hot tub
9.8 out of 10, Exceptional, (89)
"House was lovely and well appointed. Great location. Can tell homeowner thought of many details to ensure a positive guest experience. Thank you!"
United States
Danielle G.
The price is NZ$951
includes taxes & fees
26 Oct - 27 Oct
Beautiful lakefront house with full kitchen, private 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.
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

Rodeway Inn

Rodeway Inn

10/10 Excellent
"pretty safe "
Taylor 1-night trip
Posted 2 days ago
Rodeway Inn

Find out more about Middlesboro

Middlesboro Holiday Homes information

Number of reviews
271
Accommodation
174 Holiday Homes
Lowest Price
NZ$400
Highest Price
NZ$1,260

Explore a world of travel with Expedia