Photo by Alexis Wyrick

Middlesboro Holiday Rentals

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Holiday Rentals in Middlesboro

Lake front home, Hot tub, Boat dock near Flat Hollow Marina in Speedwell Tn.

9.6 out of 10, Exceptional, (50)
"We had a group of 8 adults using the 4 bedrooms. All the beds were reported as very comfortable. The home is very well stocked for larger groups with the main dining table able to seat up to 10 people comfortably. The decks are great - particularly enjoyed the swing and the hot tub on the lower level. The steps are certainly a challenge, however with some planning to limit the trips up and down, you can enjoy boating and swimming off the nice dock as we did. Very nice home with an accommodating...
Lake front home, Hot tub, Boat dock near Flat Hollow Marina 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

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

BOOK NOW FOR YOUR INTIMATE WINTER RETREAT!

10.0 out of 10, Exceptional, (38)
"Our multigenerational family had great stay at Seas the Day. Everyone had plenty of space, and the multiple refrigerators, dishwashers and ovens were especially helpful. The hosts were easy to communicate with and we were very happy that we chose to spend our Thanksgiving holiday at this location."
BOOK NOW FOR YOUR INTIMATE WINTER RETREAT!

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

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

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

Scenic 6BR lakefront home in cove with private dock, boat slips, hot tub-Dogs ok

9.4 out of 10, Exceptional, (13)
"Property was extremely nice and comfortable. Perfect location. Steps from water…as described. And they have a commercial ice maker!!! Saved money on cooler ice!"
Scenic 6BR lakefront home in cove with private dock, boat slips, hot tub-Dogs ok

Dog-friendly waterfront home with a firepit, grill, deck, board games, & dock

8.6 out of 10, Excellent, (10)
"Excellent accommodations. Loved the view, and the birds! Saw a bald Eagle!!"
Dog-friendly waterfront home with a firepit, grill, deck, board games, & dock

LAKE DAZE--Lakefront/No Wake/9br/12ba/Private Dock/Hot Tub/Sleeps 32

9.6 out of 10, Exceptional, (63)
"The only problem we had was the lake was dry and there was no dock or slide like in the picture. Other than that great property "
LAKE DAZE--Lakefront/No Wake/9br/12ba/Private Dock/Hot Tub/Sleeps 32

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...
The price is AU$736
includes taxes & fees
21 Feb - 22 Feb
Dog-friendly lake home with private floating dock - jetted tub, firepit, & decks

9Bed/9Bath Private Dock Quiet Cove Near Marinas

9.8 out of 10, Exceptional, (174)
"My family stayed at this gorgeous property for our New Years reunion. The house is very spacious and VERY well-equipped. MaryBeth was super helpful with all questions. I would recommend this beautiful place and will definitely be coming back. "
9Bed/9Bath Private Dock Quiet Cove Near Marinas

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

What a Life - Norris Lake Front House w/ dock, hot tub and NO-steps to lake

9.4 out of 10, Exceptional, (17)
"Grateful for family thanksgiving"
What a Life - Norris Lake Front House w/ dock, hot tub and NO-steps to lake

LakeFront 7 bedroom Cottage. Private Cove, no Steps to Water, golf cart!

10.0 out of 10, Exceptional, (21)
"We stay at a lot of VRBO's and AriBnB's and this was by far one of the nicest, cleanest, well stocked places we have ever been. They have thought of everything as the kitchen is very well stocked with everything you need. The pictures don't do justice. We went for Thanksgiving and also celebrated Christmas as well with our 6 kids and grandchildren. They went over and above and put up a Christmas tree for us so we could celebrate with our kids. The communication was excellent throughout the...
LakeFront 7 bedroom Cottage. Private Cove, no Steps to Water, golf cart!

Fabulous view, walking distance from Flat Hollow Marina

9.8 out of 10, Exceptional, (8)
"The location of the property was great as it was just a short walk to the marina. The porch was a wonderful retreat, too. We however, felt the property needed a good sweeping and mop job. After our 7 month old baby dropped something on the floor and it rolled under the couch, we found trash, cups, wrappers, and dust bunnies galore. We didn't realize that the floors were so dirty until we gave our 2 year old a bath, then put her in footed pj's.....Her feet were filthy. The cold air return in...
Fabulous view, walking distance from Flat Hollow Marina

Lakefront w/ Private Dock, 7 BR, Free Kayaks, Firepit, Hot Tub

9.6 out of 10, Exceptional, (79)
"far away, but it was worth it..."
Lakefront w/ Private Dock, 7 BR, Free Kayaks, Firepit, Hot Tub

Norris lakefront home with covered boat dock

10.0 out of 10, Exceptional, (53)
"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

Spring Lily Retreat - Spacious, Lakefront, Hot Tub, Private Dock, Peaceful Cove!

9.8 out of 10, Exceptional, (63)
"GREAT PLACE - PARKING IS A LITTLE HARD"
Spring Lily Retreat - Spacious, Lakefront, Hot Tub, Private Dock, Peaceful Cove!
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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Other types of properties in Middlesboro you may be interested in

Sleep Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (688)
"Clean and affordable."
The price is AU$156
includes taxes & fees
5 Mar - 6 Mar
Sleep Inn & Suites

Econo Lodge Middlesboro

2.0 star property
7.0 out of 10, Good, (364)
"I was disappointed that it said breakfast included but it was only a continental breakfast. Other than that our room was clean and the beds were so comfortable. Staff very friendly "
The price is AU$155
includes taxes & fees
9 Mar - 10 Mar
Econo Lodge Middlesboro

Holiday Inn Express Williamsburg by IHG

2.5 star property
9.0 out of 10, Wonderful, (898)
"The staff was very friendly. The beds were comfortable. Everything was clean. "
The price is AU$206
includes taxes & fees
23 Mar - 24 Mar
Holiday Inn Express Williamsburg by IHG
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.

Frequently asked questions

Are there holiday rentals in Middlesboro?

Yes, there are holiday rentals close to the most popular sights in Middlesboro, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the mountain landscape in Middlesboro. Make sure you have time to check out the churches while you're in the area.

What are some of the best holiday rentals that Middlesboro has to offer?

Waker's Paradise: Lakefront,9br/8.5ba, Private Dock,Hot Tub,Gameroom,Sleeps 32: This holiday home rental outside of Middlesboro is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 9 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with an arcade/games room and 1 hot tub.

How many holiday rentals are there in Middlesboro?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Middlesboro stay.

What’s there to see and do in Middlesboro?

Cumberland Gap National Historical Park and Kentucky Ridge State Forest are a couple of scenic spots to enjoy the outdoors, whereas Bell County Historical Society Museum is one of the cultural attractions. While here, Middlesboro Mall and Middlesboro Country Club are other places worth a visit.

What’s a holiday rental in Middlesboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middlesboro. Holiday rentals feature amenities such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for families.