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Compare 131 Vacation Homes in Middlesboro with updated reviews, rates, and availability.

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
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.

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, (59)
"Love the place super relaxing "
LAKE DAZE--Lakefront/No Wake/9br/12ba/Private Dock/Hot Tub/Sleeps 32
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
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
Spacious, lakefront home with private dock, hot tub, chic decor, & amazing views

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
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, (134)
"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
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!
Lakefront Paradise Island
Firepit overlooking the lake

Lakefront Paradise Island

10.0 out of 10, Exceptional, (9)
"This was probably the best rental that we ever stayed at. Although we only stayed a few days everything was beyond expectations. We only utilized the main floor and not the lower level of the house. We explored the whole house and everything looked to be very comfortable. The bedroom in the main floor was extremely comfortable, the living room had plenty of seating with great view out the windows of the lake. The kitchen had everything you would need. I think the kitchen was nicer than the one I...
Lakefront Paradise Island
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
American Freedom Sleeps 38; Theater Rm.; Dbl Decker Dock w/slide&2 Covered slips
American Freedom Lakefront 10 Bedrooms

American Freedom Sleeps 38; Theater Rm.; Dbl Decker Dock w/slide&2 Covered slips

9.6 out of 10, Exceptional, (5)
"The property was amazing. Well stocked for anything you may need. Manager was quick with answers and helpful.. we looked to see if availability was open in the summer because we all want to come back!!! Thank you for a great family Christmas!!"
American Freedom Sleeps 38; Theater Rm.; Dbl Decker Dock w/slide&2 Covered slips
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, (39)
"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
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!
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
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
Tranquil Cove on Norris Lake w/ Kayaks
Front view

Tranquil Cove on Norris Lake w/ Kayaks

10.0 out of 10, Exceptional, (23)
"Easy with the boat rental brought to the house."
Tranquil Cove on Norris Lake w/ Kayaks
Checkout this beautiful lakefront home on Norris Lake! Open Christmas/New Years!
Exterior

Checkout this beautiful lakefront home on Norris Lake! Open Christmas/New Years!

9.6 out of 10, Exceptional, (29)
"The property was terrific. Great floor plan. We had a great time."
Checkout this beautiful lakefront home on Norris Lake! Open Christmas/New Years!
Harlan, KY Modern Private Guesthouse 302 Historic Downtown (Vela's Villas)
Exterior

Harlan, KY Modern Private Guesthouse 302 Historic Downtown (Vela's Villas)

10.0 out of 10, Exceptional, (2)
"I was very pleased with the hospitality, having a wash room to use, and great kitchen, too. Could relax a little watching streaming channels, too."
Harlan, KY Modern Private Guesthouse 302 Historic Downtown (Vela's Villas)
Harlan, KY GuestHouse 300 Vacation/Weddings/Events (Cole Mansion)
Exterior

Harlan, KY GuestHouse 300 Vacation/Weddings/Events (Cole Mansion)

10.0 out of 10, Exceptional, (1)
"Had a few issues but they were resolved."
Harlan, KY GuestHouse 300 Vacation/Weddings/Events (Cole Mansion)
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
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
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 AED 735
AED 935 total
includes taxes & fees
3 Jan - 4 January 2025
1928 Home in the heart of Cumberland Gap
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.