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Middlesboro Vacation Rentals

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Oct 10 - Oct 12
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Dec 19 - Dec 21

Vacation Rentals in Middlesboro

Our top choices for Middlesboro vacation rentals

9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock
Smart TV, fireplace, DVD player, foosball

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

9.8 out of 10, Exceptional, (108)
"It was great! "
9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock
Family Affair, room 4 30, 15 Beds, 2 FULL Kitchens!!! Huge dock w 2 boat slips
Property grounds

Family Affair, room 4 30, 15 Beds, 2 FULL Kitchens!!! Huge dock w 2 boat slips

10.0 out of 10, Exceptional, (90)
"The home was great and we had plenty of room for 15 of us. The lake was great and the boat dock. Everyone loved the space, pool table and games. My only issue for me and my husband was, we are both 65 and the stairs gave us a challenge, but we did it. The owners were amazing and very accommodating. We really enjoyed the home and our stay. "
Family Affair, room 4 30, 15 Beds, 2 FULL Kitchens!!! Huge dock w 2 boat slips
LAKE DAZE--Lakefront/No Wake/9br/12ba/Private Dock/Hot Tub/Sleeps 32
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (69)
"We loved the property! We all had a great time! Thank you!"
LAKE DAZE--Lakefront/No Wake/9br/12ba/Private Dock/Hot Tub/Sleeps 32
Forget Me Not Haven – 6BR Lakefront Home for Unforgettable Family Memories
Terrace/patio

Forget Me Not Haven – 6BR Lakefront Home for Unforgettable Family Memories

Forget Me Not Haven – 6BR Lakefront Home for Unforgettable Family Memories
Dog-friendly waterfront home with a firepit, grill, deck, board games, & dock
Fridge, microwave, oven, stovetop

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

8.2 out of 10, Very Good, (17)
"Cozy and comfortable. I loved having 2 slips available for my boat and jet sky. I also liked the privacy and view to the lake."
Dog-friendly waterfront home with a firepit, grill, deck, board games, & dock
Slip-Away into Isolation & Relaxation w/ Covered Dock & Hot Tub.
Private kitchen

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

9.4 out of 10, Exceptional, (9)
"The house was clean and as stated in the listing. Hank was very quick to respond. Good location close to Powell valley Marina. "
Slip-Away into Isolation & Relaxation w/ Covered Dock & Hot Tub.
Book your fall retreat today!
Property grounds

Book your fall retreat today!

10.0 out of 10, Exceptional, (51)
"So perfect place"
Book your fall retreat today!
Waker's Paradise: Lakefront,9br/8.5ba, Private Dock,Hot Tub,Gameroom,Sleeps 32
Interior

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

9.8 out of 10, Exceptional, (49)
"We stayed at this property with 21 family members for a week. The house was absolutely beautiful and the dock was amazing! The property manager was amazing to communicate with. Definitely a great vacation!!!"
Waker's Paradise: Lakefront,9br/8.5ba, Private Dock,Hot Tub,Gameroom,Sleeps 32
9Bed/9Bath Private Dock Quiet Cove Near Marinas
Property grounds

9Bed/9Bath Private Dock Quiet Cove Near Marinas

9.8 out of 10, Exceptional, (185)
"Beautiful house! Everything exceptional except being on a hill with lots of steps! "
9Bed/9Bath Private Dock Quiet Cove Near Marinas
Mountain Lake Retreat w/ Concrete Walkway w/ Kayaks
Outdoor spa tub

Mountain Lake Retreat w/ Concrete Walkway w/ Kayaks

9.6 out of 10, Exceptional, (35)
"Everything was great. "
Mountain Lake Retreat w/ Concrete Walkway w/ Kayaks
Waterfront home with game room, theater, deck, dock & fireplace
Property grounds

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

10.0 out of 10, Exceptional, (47)
"The house and location was perfect, would definitely stay here again. Host was very responsive with any questions."
Waterfront home with game room, theater, deck, dock & fireplace
Beautiful lakefront house with full kitchen, private dock, & hot tub
Terrace/patio

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

9.8 out of 10, Exceptional, (87)
"Our family had a wonderful stay at this awesome lake house! Awesome views and would definitely come back! Thanks for sharing your home with our family!"
Beautiful lakefront house with full kitchen, private dock, & hot tub
Beautiful Norris Lake Front A-Frame with Private Dock in Speedwell, Tn .
Property grounds

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

9.8 out of 10, Exceptional, (49)
"Had an absolute blast at this house. It was great and the hosts were super responsive"
Beautiful Norris Lake Front A-Frame with Private Dock in Speedwell, Tn .
Treasure Cove, Waterfront, 9 Bed/9 Bath, Double Decker Dock, arcade games
Property grounds

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

9.8 out of 10, Exceptional, (46)
"We had a great stay here! Everyone loved having their own bathrooms and the house had everything we needed! "
Treasure Cove, Waterfront, 9 Bed/9 Bath, Double Decker Dock, arcade games
Wakes N Shades-Brand New. Private Dock. Hot Tub. 9 Bed/12 Bath.Theater Room
Exterior

Wakes N Shades-Brand New. Private Dock. Hot Tub. 9 Bed/12 Bath.Theater Room

9.6 out of 10, Exceptional, (17)
"We had a great time! The house was perfect with plenty of room for everyone and the kitchen was well stocked for all our cooking needs. We loved the upper deck on the dock! "
Wakes N Shades-Brand New. Private Dock. Hot Tub. 9 Bed/12 Bath.Theater Room
Lakefront Paradise Island
Outdoor dining

Lakefront Paradise Island

9.6 out of 10, Exceptional, (9)
"This is an ideal lakefront property and well taken care of. We had a great time!"
Lakefront Paradise Island
American Freedom; Theater Rm! Enjoy the Fall Colors! Flexible Chk-in & out times
Exterior

American Freedom; Theater Rm! Enjoy the Fall Colors! Flexible Chk-in & out times

9.8 out of 10, Exceptional, (10)
"The house was much more then we expected. Clean, very equipped kitchen, easy access to the lake. Going back next year!!!! Need a great house for large family or alot of friends this is the house. "
American Freedom; Theater Rm! Enjoy the Fall Colors! Flexible Chk-in & out times
Dog-friendly lakefront house with hot tub, central AC, & mountain view
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (17)
"Loved the property, everything you need for a nice family lake vacation."
Dog-friendly lakefront house with hot tub, central AC, & mountain view
Lakefront home at Tumbling Run Estates w/ Kayaks
Fridge, microwave, oven, stovetop

Lakefront home at Tumbling Run Estates w/ Kayaks

9.6 out of 10, Exceptional, (19)
"Excellent location and great place to stay. "
Lakefront home at Tumbling Run Estates w/ Kayaks
Lakefront w/ Private Dock, 7 BR, Free Kayaks, Firepit, Hot Tub
Outdoor spa tub

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

9.6 out of 10, Exceptional, (86)
"A little tired but appropriate for the money. It had everything we needed. I’d rent it again. "
Lakefront w/ Private Dock, 7 BR, Free Kayaks, Firepit, 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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Top Middlesboro Hotel Reviews

Days Inn by Wyndham Jellico - Tennessee State Line

Days Inn by Wyndham Jellico - Tennessee State Line

10/10 Excellent
"Clean newly remodeled spacious room. Comfortable bed. Parked at our door. Quiet. Friendly staff. Comfortable tub. Hot water plentiful. Serene surroundings. Cute small town. Could use more lighting around mirror at the sink. Good value. Highly recommended."
Terri 1-night trip
Posted 3 days ago
Days Inn by Wyndham Jellico - Tennessee State Line

Find out more about Middlesboro

Find out more about Middlesboro

Search for holiday rentals in Middlesboro on Expedia! You can easily find your home rentals, villas, holiday apartments in Middlesboro using one of the methods below:

  • View our selection of featured holiday rentals in Middlesboro
  • Use the map to find apartments and other holiday homes in the Middlesboro neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middlesboro while they last

Look no further and take a look at our great range of rental properties in Middlesboro!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Middlesboro?

Yes, we offer vacation rentals close to the most popular sights in Middlesboro, or you can choose a secluded option if you'd like a relaxing place to 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's the top vacation rental that Middlesboro has to offer?

Beautiful Norris Lake Front A-Frame with Private Dock in Speedwell, Tn .: This vacation home rental near Middlesboro is located on a lake and has a balcony, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals are there in Middlesboro?

With 5 Expedia vacation rentals, you're sure to find just the right place for your Middlesboro stay.

What’s there to see and do in Middlesboro?

Cultural attractions include Bell County Historical Society Museum, whereas Kentucky Ridge State Forest is a spot to enjoy nature. While here, Middlesboro Country Club and Middlesboro Mall are other places worth a visit.

What’s a vacation rental in Middlesboro like?

Vacation rentals are private properties you can stay in for short or long periods in Middlesboro. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for small groups.