Photo by Alexis Wyrick

Search Vacation Homes in Middlesboro

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 151 Vacation Homes in Middlesboro with updated reviews, rates, and availability.

1928 Home in the heart of Cumberland Gap

9.8 out of 10, Exceptional, (80)
"Nice spot that is conveniently located in Cumberland Gap. Highly recommend!!!"
The price is SAR 750
SAR 955 total
includes taxes & fees
19 Mar - 20 Mar
1928 Home in the heart of Cumberland Gap

Beautiful Norris Lake Front A-Frame with Private Dock in Speedwell, Tn .

9.8 out of 10, Exceptional, (40)
"Perfect location on Norris with lovely view and steps down to the lake. House was very nice and had everything you needed. Host was very responsive with any questions. Loved that there was a pontoon available to rent. We had a great stay! "
Beautiful Norris Lake Front A-Frame with Private Dock in Speedwell, Tn .

Entertainment in Abundance, Putting Green, Games, Kayaks, No-wake Covered Dock!

9.2 out of 10, Wonderful, (5)
"My family enjoyed our stay."
Entertainment in Abundance, Putting Green, Games, Kayaks, No-wake Covered Dock!

Beautiful lakefront house with full kitchen, private dock, & hot tub

9.8 out of 10, Exceptional, (78)
"The home was beautiful. On the water and awesome view of Lake Norris. Surrounding neighborhood (1 mile from lake) not as well off. We did contact management about a very bad smell (seemed like septic smell) coming from the first floor restroom. After a couple days maintenance person came out. Told us issue was fixed and smell would dissipate, but it didn’t. We just got used to it, but noticed it each time we left and came back inside. Hope they’re able to fix this for next renters. House could...
Beautiful lakefront house with full kitchen, private dock, & hot tub

Norris lakefront home with covered boat dock

10.0 out of 10, Exceptional, (54)
"This was one of the best houses I have stayed at. Best stocked house ever! Will definitely be back! "
Norris lakefront home with covered boat dock

Waker's Paradise: Lakefront,9br/8.5ba, Private Dock,Hot Tub,Gameroom,Sleeps 32

9.6 out of 10, Exceptional, (41)
"We visited this place with a large company and spent this time with a lot of emotions. Everyone had equal conditions for rest and everyone was satisfied! The only thing that upsets is the lack of a pier near the water. There was no opportunity to enjoy the quiet atmosphere of nature by dipping our feet in the water. But this did not prevent our company from spending this time unforgettable)))"
Waker's Paradise: Lakefront,9br/8.5ba, Private Dock,Hot Tub,Gameroom,Sleeps 32

Breathtaking Lake View with a Private Dock in Year Around Water

10.0 out of 10, Exceptional, (39)
"The property was beautiful. It was just as described. The view was wonderful. We had a great time. Hope to return."
Breathtaking Lake View with a Private Dock in Year Around Water

Quiet Cove on the Quiet Side of the Lake

9.8 out of 10, Exceptional, (17)
"Black Dog Lake House was exactly as advertised. A nice property located in a secluded cove on Norris Lake. Well appointed, with separate living spaces for the adults and our teen son (who had the downstairs 'man cave' to himself). We really enjoyed the visit!"
Quiet Cove on the Quiet Side of the Lake

Lake Front 2-Bedroom Home W/ Privacy! Beautiful Views & Numerous Amenities...

9.8 out of 10, Exceptional, (150)
"Great spot, highly recommend!"
Lake Front 2-Bedroom Home W/ Privacy! Beautiful Views & Numerous Amenities...

Lakefront Getaway at Swan Seymour w/ Kayaks

10.0 out of 10, Exceptional, (30)
"This was our second trip to Lake Norris for a family get together and we will definitely return to this property. The house and property have everything you need to have a great time from the time you get up to the time you go to bed. Due to the timing of our stay we were not able to rent a boat but er still utilized the great dock. We used the kayaks that are provided and did a lot of cove to cove exploring. The house is very well equipped with all the comforts of home. We enjoyed using the...
Lakefront Getaway at Swan Seymour w/ Kayaks

Breathtaking 6Bd/6 Bath/PRIVATE DOCK All The Bells and Whistles!

9.8 out of 10, Exceptional, (61)
"We came to SkyFall for our Thanksgiving family get away trip. It was a great house that was very clean. Only a few negative things. 1). I booked this house for use of the golf cart for my older parents so they could go see lake because I knew we were up high. However, apparently it’s not available during off season. Although it wasn’t listed as the on the VRBO sight. If I would have known this, we would have brought our own ATV for them. It changed our trip a lot unfortunately and our...
Breathtaking 6Bd/6 Bath/PRIVATE DOCK All The Bells and Whistles!

Slip-Away into Isolation & Relaxation w/ Covered Dock & Hot Tub.

10.0 out of 10, Exceptional, (1)
"Very good. Nice clean, spacious place with a good view of the river."
Slip-Away into Isolation & Relaxation w/ Covered Dock & Hot Tub.

Lakefront Escape on Norris Lake w/ Kayaks

9.8 out of 10, Exceptional, (26)
"We absolutely loved the lake house—it was majestic! This home exceeded our expectations in every way. It was impeccably clean, and everything was top-notch. As you drive up to the property, the massive lake unfolds before you—so beautiful and calm. After parking in front of the one-car garage, entering the house is a delightful experience. From the stunning granite countertops to the real canoe hanging over the kitchen island, every detail is amazing. The kitchen is spacious, with five bar...
Lakefront Escape on Norris Lake w/ Kayaks

Old Southern - Lakefront - Dog friendly

10.0 out of 10, Exceptional, (8)
"My family and I enjoyed our 5 nights stay, Norris Lake has been one of the best lakes we've been to and really enjoyed the location. Thank you for the hospitality! The Dillera Family (Fort Worth, TX)"
Old Southern - Lakefront - Dog friendly

Blissful Bungalow across from LMU campus

9.6 out of 10, Exceptional, (21)
"visiting family at lmu, very close! We had a great weekend, would stay again! "
Blissful Bungalow across from LMU campus

Waterfront home with game room, theater, deck, dock & fireplace

10.0 out of 10, Exceptional, (34)
"everyone had a great time, they think this is the best one for all of our families, plenty games to play since we went for our family Christmas and didn't use the lake access to keep busy. simple love this home!"
Waterfront home with game room, theater, deck, dock & fireplace

BOOK NOW FOR YOUR INTIMATE WINTER RETREAT!

9.8 out of 10, Exceptional, (39)
"Beautiful home and setting. We did not notice that sheets weren't on the bed and everybody was having to make beds after midnight. One of the King beds had Queen sheets. We had to make do for the night and it was suckling resolved the next day"
BOOK NOW FOR YOUR INTIMATE WINTER RETREAT!

Spacious, lakefront home with private dock, hot tub, chic decor, & amazing views

9.8 out of 10, Exceptional, (65)
"One of the cleanest rentals we have stayed in. Great spaces and excellent seating options both inside and out!"
Spacious, lakefront home with private dock, hot tub, chic decor, & amazing views

Newly Renovated Norris Lake Home with Private Dock

9.6 out of 10, Exceptional, (24)
"Stayed with three generations of family for New Years Eve. The house was wonderful for both the youngest and the oldest. We were 5 adults, 5 children and 2 teenagers and there was plenty of room. The bedrooms are super spacious with so much closet space, which really helped keeping the kids organized. The kitchen was amazing for big family meal preparations! They had everything we needed to cook for 12!I also have to say after staying at several Norris lake vacation homes that the road to this...
Newly Renovated Norris Lake Home with Private Dock

9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock

9.8 out of 10, Exceptional, (101)
"So wonderful! Gate and lock codes ahead of time and perfect. And the property is amazing! Super clean and prepared. Great views of the lake. Super stocked kitchen with crock pots and utensils. Enough room for the whole family to gather to eat and swap presents, but space to spread out and let teens hang out, the preteens play ideo games, and adults talk and catch up. Excellent stay! "
9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock
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.
Don't see what you're looking for?
See all available properties in Middlesboro
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Middlesboro

Cozy 2-bedroom Lustron home located in Middlesboro, Ky, Easy walk to downtown!

The price is SAR 446
SAR 790 total
includes taxes & fees
19 Mar - 20 Mar
Cozy 2-bedroom Lustron home located in Middlesboro, Ky, Easy walk to downtown!

Lakefront home with private dock and boat launch - dog-friendly & central AC

9.6 out of 10, Exceptional, (28)
"Lovely home overlooking beautiful view of the inlet and lake. Two porches to enjoy -- one is screened. Very clean and didn't smell like dog! Super quiet and remote neighborhood."
Lakefront home with private dock and boat launch - dog-friendly & central AC

Dog-friendly lake home with private floating dock - jetted tub, firepit, & decks

6.8 out of 10, (13)
"To begin with the oven wasn’t working and after many calls and a few hours we were able to get into the electric box to flip it on. The rental company does not provide cleaning supplies due to their policy because it is poison. That’s what the proper manager told us. So the kitchen cabinets were filled with house feces and all we had to clean it with was dish soap. Also, the coffee pot had mold and old coffee grinds. Again nothing to clean with. They knew this on Wednesday night and we stayed...
Dog-friendly lake home with private floating dock - jetted tub, firepit, & decks
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.