Photo by Alexis Wyrick

Holiday Rentals in Middlesboro

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Holiday Rentals in Middlesboro

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

9.6 out of 10, Exceptional, (77)
"This was the perfect place for our group of families to get together for Thanksgiving. Plenty of bedrooms and awesome kitchen and gathering spaces. All was exactly as advertised and very clean."
Lakefront w/ Private Dock, 7 BR, Free Kayaks, Firepit, Hot Tub

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

Sleeps 25/PRIVATE DOCK CHEF KITCHEN WITH ICE MAKER! Great fire pit, game area

9.8 out of 10, Exceptional, (135)
"Family from Louisiana, Maryland, and Pennsylvania met at Comfort Life for a grand Thanksgiving celebration, Nice chilly weather, beautiful home, excellent amenities. Loved the kitchen. Bedrooms, bathrooms were very clean and comfortable. Had a little trouble finding the rental. NEED to follow directions carefully, Cabin had excellent WiFi, but phone service was spotty."
Sleeps 25/PRIVATE DOCK CHEF KITCHEN WITH ICE MAKER! Great fire pit, game area

"Our Happy Place", Floating Home, Sleeps 10; 4 bed/1.5 bath

10.0 out of 10, Exceptional, (13)
"Beautiful accommodations with everything we could need and more."
"Our Happy Place", Floating Home, Sleeps 10; 4 bed/1.5 bath

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

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

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

9.8 out of 10, Exceptional, (60)
"Love the place super relaxing "
LAKE DAZE--Lakefront/No Wake/9br/12ba/Private Dock/Hot Tub/Sleeps 32

Come Enjoy Fall at Norris Lake! Firepit. HotTub. Beautiful views! Quiet Cove.

9.6 out of 10, Exceptional, (97)
"We had a group of 16 ladies staying for a weekend. The house was perfect for us. We had a small problem with a toilet, and the owner answered quickly when we called. We would definitely stay here again!!"
Come Enjoy Fall at Norris Lake! Firepit. HotTub. Beautiful views! Quiet Cove.

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

10.0 out of 10, Exceptional, (33)
"Lightening was not adequate for game playing no overhead lights "
Waterfront home with game room, theater, deck, dock & fireplace

Norris Nook: Lakefront 9br/11ba, Private Dock,Private HotTub,Sleeps 32, Gameroom

10.0 out of 10, Exceptional, (47)
"I would highly recommend this home to friends we had more than enough room.The kitchen had me not wanting to be anywhere else.The kids never wanted to leave the games, it’s very quiet I would lease this home again, we were a group of 24 . Y Jackson"
Norris Nook: Lakefront 9br/11ba, Private Dock,Private HotTub,Sleeps 32, Gameroom

Three-story lake-view cabin with private hot tub, pool table, fireplace & AC

9.6 out of 10, Exceptional, (22)
"We rented this cabin for the weekend just to celebrate a birthday and a graduation. The cabin was great. It was extremely clean. The kitchen had everything we needed. We will definitely stay again."
Three-story lake-view cabin with private hot tub, pool table, fireplace & AC

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!

1928 Home in the heart of Cumberland Gap

9.8 out of 10, Exceptional, (76)
"Adorable house perfectly located in Cumberland Gap. "
The price is €254
includes taxes & fees
4 Jan - 5 Jan
1928 Home in the heart of Cumberland Gap

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

Dog-friendly lakefront house with hot tub, central AC, & mountain view

9.6 out of 10, Exceptional, (11)
"Property exactly as pictured. Lots of space and very well equipped. Nice decoration. Good communication for small hiccup. Don’t hesitate to book"
Dog-friendly lakefront house with hot tub, central AC, & mountain view

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

7.0 out of 10, Good, (12)
"Absolutely amazing property. The house is beautiful and well taken care of. Access to the lake was amazing as well really enjoyed our visit"
The price is €489
includes taxes & fees
8 Jan - 9 Jan
Dog-friendly lake home with private floating dock - jetted tub, firepit, & decks

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

Custom Norris Lake home in no-wake zone w/ hot tub & two kitchens - dog-friendly

8.6 out of 10, Excellent, (8)
"Overall good. Major problem with heating. Thermostats difficult to regulate.Some areas very cold others too hot. Property manager responded quickly. Tried to adjust room vents. This didn’t improve the temperature control much."
Custom Norris Lake home in no-wake zone w/ hot tub & two kitchens - dog-friendly

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, (76)
"This house is gorgeous and it has everything you need for the lake. We had a great time! I will sure book this house again. Lovely property and paradise view!! "
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.
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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, (666)
"Great view, clean and kind staff. Love they have posted quiet hours."
The price is €99
includes taxes & fees
23 Jan - 24 Jan
Sleep Inn & Suites

Econo Lodge Middlesboro

2.0 star property
7.0 out of 10, Good, (356)
"Elevator to upper floors was nice esp if you have lots of luggage or are unable to do stairs. Bed was very comfortable, hot water was hot and for a decent shower, room was very clean and updated. 2 places to eat-Mexican Food and Drive in that were easy to walk to. Continental breakfast was very accommodating. It was a very nice place to stay. Will definitely stay again if I am in the area. "
The price is €94
includes taxes & fees
26 Jan - 27 Jan
Econo Lodge Middlesboro

Boone Trail Inn

2.0 star property
7.0 out of 10, Good, (78)
"Very peaceful. Clean"
The price is €84
includes taxes & fees
3 Feb - 4 Feb
Boone Trail Inn
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?

Lakefront w/ Private Dock, 7 BR, Free Kayaks, Firepit, Hot Tub: This holiday home rental outside of Middlesboro is located on a lake, and has a balcony, a selection of games and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 Country Club and Middlesboro Mall 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.