Middlesboro Vacation Rentals : Short-Term Rentals for 2025

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Vacation Rentals in Middlesboro

"The house have space for everyone the kitchens have a lots things to use."

"Great experience- accurate listing that ensured space for all!"

"Wonderful vacation"

"We had a wonderful time. The place had everything we needed, was clean, and provided the perfect setting for our family vacation. "

"We really liked the location of this home and the views were beautiful! There were plenty of amenities to meet our needs."

Smart TV, fireplace, DVD player, foosball

"It was great! "

"Enjoyed the view and the property"

"We really enjoyed our stay! The property was beautiful!"

"So perfect place"

"The weather was chilly but overall we had a great stay and it was a great property"

"Loved the lake and the view."

"Awesome house!"

"Excellent location and great place to stay. "

"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!"

"Host was amazing with their information and house had everything we needed!"

"Love the place super relaxing "

"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. "

"Awesome house!! Great views and plenty of room. I would stay here again."

"Wonderful play to stay."

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Top Middlesboro Hotel Reviews

Pine Mountain State Resort Park

10/10 Excellent

"I started out in one of the original cabins. My toilet didn’t work so the staff put me up in a room at the lodge. The room was clean and had a beautiful view. The staff went above and beyond to see that my stay was enough to rank a return visit in the future. I can say that I will definitely be back again. "

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

10/10 Excellent

"It was a quick visit (and we had one great weather day and the rest overcast and/or rainy), but were very comfortable at the house. It was impeccably clean and we had a great time out on the water - we used the pontoon, what a huge convenience, and well-maintained. Carmen was very responsive and we had no problems. We forgot our roku stick so were a little limited in what we could watch, but that's on us, and we managed fine. The wifi worked great and there were tons of games for us to play! Thanks for the fun! "

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

10/10 Excellent

"Our family of 25, ranging in age from 1 to 60, spent 7 nights at Lake Daze and could not have asked for a better experience. The home was spacious enough for all of us to be under one roof while still allowing everyone to have their own space when needed.From early morning coffee with a view to late-night laughter around the table, Lake Daze gave us the perfect backdrop to share old family stories and create new ones. The property was clean, well-stocked, and thoughtfully set up for large groups—everything from the kitchen essentials to the gathering spaces made our stay comfortable and stress-free.The location made it easy to enjoy both relaxing downtime and fun family activities, and the owners clearly take pride in making sure guests feel welcome.If you’re looking for a place to bring the whole family together, Lake Daze is it. We left with full hearts, a lot of laughs, and memories we’ll treasure forever. We can’t wait to come back!"

Find out more about Middlesboro

Everything you need to know about Middlesboro vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middlesboro vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middlesboro vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middlesboro vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middlesboro. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middlesboro vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlesboro vacation rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middlesboro rentals

At Expedia, we put the best Middlesboro vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middlesboro rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middlesboro vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middlesboro. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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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.

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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

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

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 .

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

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

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

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

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

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

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

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

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

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

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

Book your fall retreat today!

Book your fall retreat today!

9Bed/9Bath Private Dock Quiet Cove Near Marinas

9Bed/9Bath Private Dock Quiet Cove Near Marinas

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

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,

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

Lakefront home at Tumbling Run Estates w/ Kayaks

Lakefront home at Tumbling Run Estates w/ Kayaks

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

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

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

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

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

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

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

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

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

Top Middlesboro Hotel Reviews

Pine Mountain State Resort Park

Find out more about Middlesboro

Find out more about Middlesboro

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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Frequently asked questions