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Middlesboro Vacation Rentals

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Vacation Rentals in Middlesboro

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

10.0 out of 10, Exceptional, (89)
"The house have space for everyone the kitchens have a lots things to use."
Family Affair, room 4 30, 15 Beds, 2 FULL Kitchens!!! Huge dock w 2 boat slips

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

9.8 out of 10, Exceptional, (48)
"Great experience- accurate listing that ensured space for all!"
Waker's Paradise: Lakefront,9br/8.5ba, Private Dock,Hot Tub,Gameroom,Sleeps 32

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

10.0 out of 10, Exceptional, (48)
"Wonderful vacation"
Beautiful Norris Lake Front A-Frame with Private Dock in Speedwell, Tn .

Great Escape is Waterfrnt, 9 bdrms, perfect for family vacations and holidays

9.8 out of 10, Exceptional, (75)
"We had a wonderful time. The place had everything we needed, was clean, and provided the perfect setting for our family vacation. "
Great Escape is Waterfrnt, 9 bdrms, perfect for family vacations and holidays

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

8.2 out of 10, Very good, (17)
"We really liked the location of this home and the views were beautiful! There were plenty of amenities to meet our needs."
Dog-friendly waterfront home with a firepit, grill, deck, board games, & dock

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

9.8 out of 10, Exceptional, (107)
"It was great! "
9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock

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

10.0 out of 10, Exceptional, (31)
"Enjoyed the view and the property"
LakeFront 7 bedroom Cottage. Private Cove, no Steps to Water, golf cart!

Book now for Summer! We still have some prime dates available.

9.6 out of 10, Exceptional, (25)
"We really enjoyed our stay! The property was beautiful!"
Book now for Summer! We still have some prime dates available.

Book your fall retreat today!

10.0 out of 10, Exceptional, (50)
"So perfect place"
Book your fall retreat today!

9Bed/9Bath Private Dock Quiet Cove Near Marinas

9.8 out of 10, Exceptional, (184)
"The weather was chilly but overall we had a great stay and it was a great property"
9Bed/9Bath Private Dock Quiet Cove Near Marinas

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

9.8 out of 10, Exceptional, (45)
"Loved the lake and the view."
Treasure Cove, Waterfront, 9 Bed/9 Bath, Double Decker Dock, arcade games

9 bdrm covered dock, firepit and large bar on water, Baltic hot tub, sleeps 26,

10.0 out of 10, Exceptional, (3)
"Awesome house!"
9 bdrm covered dock, firepit and large bar on water, Baltic hot tub, sleeps 26,

Lakefront home at Tumbling Run Estates w/ Kayaks

9.6 out of 10, Exceptional, (18)
"Excellent location and great place to stay. "
Lakefront home at Tumbling Run Estates w/ Kayaks

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

10.0 out of 10, Exceptional, (43)
"We had an amazing stay at Percy’s Cove. The home had everything we needed and was very clean. We would definitely stay here again!"
Secluded No Wake Cove - Private Covered Dock-Screened Porch-Kayaks

Lakefront House at Summer Breeze w/ Private Dock w/ Kayaks

10.0 out of 10, Exceptional, (25)
"Host was amazing with their information and house had everything we needed!"
Lakefront House at Summer Breeze w/ Private Dock w/ Kayaks

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

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

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

9.8 out of 10, Exceptional, (66)
"Love the place super relaxing "
LAKE DAZE--Lakefront/No Wake/9br/12ba/Private Dock/Hot Tub/Sleeps 32

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

9.6 out of 10, Exceptional, (17)
"This was our 2nd year staying & it was amazing! Plenty of sleeping space & we could all enjoy meals together because the tables are big enough. "
Wakes N Shades-Brand New. Private Dock. Hot Tub. 9 Bed/12 Bath.Theater Room

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

10.0 out of 10, Exceptional, (45)
"Awesome house!! Great views and plenty of room. I would stay here again."
Waterfront home with game room, theater, deck, dock & fireplace

Rock of Ages: 2 Covered Slips, dble decker dock w/slide in deep water quiet cove

9.4 out of 10, Exceptional, (51)
"Wonderful play to stay."
Rock of Ages: 2 Covered Slips, dble decker dock w/slide in deep water quiet 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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Top Middlesboro Hotel Reviews

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?

Waker's Paradise: Lakefront,9br/8.5ba, Private Dock,Hot Tub,Gameroom,Sleeps 32: This vacation home rental near Middlesboro is located on a lake and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with an arcade game room and a hot tub.

How many vacation rentals are there in Middlesboro?

With 4 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?

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 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.