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Compare 135 Vacation Homes in Middlesboro with updated reviews, rates, and availability.

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

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

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
Secluded No Wake Cove - Private Covered Dock - Screened Porch - Kayaks - Netflix
The house has a beautiful view of the water year round

Secluded No Wake Cove - Private Covered Dock - Screened Porch - Kayaks - Netflix

10.0 out of 10, Exceptional, (33)
"Olga was an extremely responsive property owner & the house was very well-appointed overall! Definitely the most modernly decorated of any rental we've ever stayed at & the bedding was the coziest!! We would recommend this property to anyone! "
Secluded No Wake Cove - Private Covered Dock - Screened Porch - Kayaks - Netflix
Dock Holiday – Lakefront, Sleeps 19
Exterior

Dock Holiday – Lakefront, Sleeps 19

9.6 out of 10, Exceptional, (5)
"Overall this home accommodated a few more guests than I expected to go and had more than enough room! Would recommend if you like relaxing on the porch or great for family get togethers! Will be booking again in the near future."
Dock Holiday – Lakefront, Sleeps 19
Nauti & Nice @ Norris - a copious cozy cabin on the cove
Exterior

Nauti & Nice @ Norris - a copious cozy cabin on the cove

10.0 out of 10, Exceptional, (29)
"Such a perfect spot for a family vacation! The house was so much nicer than the photos depict. We loved the roominess, the accessibility to the dock and the screened in porch. Fran was fantastic to work with! We can’t wait to return next year!"
Nauti & Nice @ Norris - a copious cozy cabin on the cove
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Living area

Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

The price is SAR 372
SAR 1,030 total
includes taxes & fees
14 Jan - 15 Jan
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
LAKE DAZE--Lakefront/No Wake/9br/12ba/Private Dock/Hot Tub/Sleeps 32
Main Level

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

9.8 out of 10, Exceptional, (60)
"Second year at Lake Daze. Had a great time. No complaints. "
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.
Big, bright open concept floor plan

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

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

10.0 out of 10, Exceptional, (34)
"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
Main Living Room

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
BOOK NOW FOR YOUR INTIMATE WINTER RETREAT!
Decking facing the lake.

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

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 SAR 751
SAR 955 total
includes taxes & fees
13 Jan - 14 Jan
1928 Home in the heart of Cumberland Gap
Waker's Paradise: Lakefront,9br/8.5ba, Private Dock,Hot Tub,Gameroom,Sleeps 32
Living area

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
NEW LISTING! 5Bed 3Bath Lakefront Retreat, 2 slip dock, sun deck & slide!
Property grounds

NEW LISTING! 5Bed 3Bath Lakefront Retreat, 2 slip dock, sun deck & slide!

9.4 out of 10, Exceptional, (3)
"We've been coming to Norris Lake every summer for many years, so we've stayed in our fair share of houses. This house was great!! We had 4 teenage boys and 4 adults, and there were several beds we didn't even use - tons of room. The house has every possible game you can imagine - darts, ping pong, carpet ball, corn hole, foosball, and more! This was a lot of fun in the evenings once we came up from the lake. The interior of the house is very modern and clean, comfortable furniture/beds, etc. 2...
NEW LISTING! 5Bed 3Bath Lakefront Retreat, 2 slip dock, sun deck & slide!
Serenity Cove 3 Bedroom Home on Secluded Cove
Lake

Serenity Cove 3 Bedroom Home on Secluded Cove

9.8 out of 10, Exceptional, (16)
"Loved it"
Serenity Cove 3 Bedroom Home on Secluded Cove
Lakefront Cottage with Private Dock on Norris Lake
Breathtaking Lake and Mountain Views from deck

Lakefront Cottage with Private Dock on Norris Lake

9.6 out of 10, Exceptional, (5)
"I had a fantastic experience renting from JP. He was incredibly helpful and flexible, making sure that everything was just right for our stay. The house itself was exactly what we were hoping for. We were able to easily dock our jet skis and pontoon boat in the deep water dock, and the view from the house was absolutely stunning. The interior was immaculate and cozy, with a well-equipped kitchen and private bathrooms for each bedroom. Additionally, having a small boat ramp nearby saved us a lot...
Lakefront Cottage with Private Dock on Norris Lake
Best cove on Norris – no wake, near marina's & jumping bridge
Lakefront home with 3 decks overlooking a cove. Private 2-story dock w/ slide.

Best cove on Norris – no wake, near marina's & jumping bridge

9.8 out of 10, Exceptional, (40)
"Sara was very responsive and considerate of all necessary house information. The rental was clean, spacious, in a great location (close to jump bridge & marinas), and had access to the water. We very much enjoyed our stay!"
Best cove on Norris – no wake, near marina's & jumping bridge
Treasure Cove, Waterfront, 9 Bed/9 Bath, Double Decker Dock, arcade games
Open livingroom, kitchen and dining area with table for 12 and bar table for 4

Treasure Cove, Waterfront, 9 Bed/9 Bath, Double Decker Dock, arcade games

9.8 out of 10, Exceptional, (43)
"Our family, ages from 4 years to 78 years, have been coming to Lakeside Estates on Norris Lake for 10 years. This was the nicest location we've stayed at so far. Everyone was very happy to have their own bathroom. If you are thinking you'll need all of the bed spaces, it is worth reaching out to the owners to clarify the beds in a few of the bed+bunk+trundle. The house also has multiple fold-away twin bed cushions to help if you have lots of kids to shift around various rooms. The kitchen/dining...
Treasure Cove, Waterfront, 9 Bed/9 Bath, Double Decker Dock, arcade games
Trail Paradise: Garage Access, Prime Location!
Enjoy a refreshing getaway when you book a stay in our charming 2 Bedroom House in Tennessee!

Trail Paradise: Garage Access, Prime Location!

10.0 out of 10, Exceptional, (25)
"That was actually my 3rd time staying at that specific house. It’s conveniently located near town and the property offers plenty of space for multiple vehicles with the two car garage. My only complaint would be the internet. When you spend all day hunting in the woods, it would have been nice if the WiFi could have supported the use of phones and television."
Trail Paradise: Garage Access, Prime Location!
Tackett Creek Retreat A
Exterior

Tackett Creek Retreat A

10.0 out of 10, Exceptional, (5)
"We stayed here and rode Tackett Creek on SxS and ATVs. Perfect location! 4 days of riding and didn't run out of places to go, with around 100 miles each day of riding. This place was perfect to come back to each day. Owner was extremely responsive to messages and very helpful with all questions. The place was very clean and HUGE for our group of 6. We will definitely be back and i would recommend this place to anyone, whether riding or just looking to relax."
Tackett Creek Retreat A
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 property types in Middlesboro

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

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
1928 Home in the heart of Cumberland Gap

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 SAR 751
SAR 955 total
includes taxes & fees
13 Jan - 14 Jan
1928 Home in the heart of Cumberland Gap
Dog-friendly waterfront home with a firepit, grill, deck, board games, & dock

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
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.