Title: Middlesboro Vacation Rentals from CA $727: Short-Term Rentals for 2026 | Expedia.ca

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![mountain view](https://images.trvl-media.com/place/8853/4dcad675-90c8-4311-844e-cc929dfd2557.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/8853/4dcad675-90c8-4311-844e-cc929dfd2557.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 17 - Jul 19](https://www.expedia.ca/Hotel-Search?regionId=8853&startDate=2026-07-17&endDate=2026-07-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Middlesboro vacation rentals

![House (2 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/122000000/121200000/121199100/121199061/7b8fb7b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121200000/121199100/121199061/2fd54d29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121200000/121199100/121199061/3ebc65a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121200000/121199100/121199061/e44cf9e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peaceful & Private! Pet-friendly Williamsburg Home

[](https://www.expedia.ca/Williamsburg-Hotels-Peaceful-Private-Pet-Friendly-Williamsburg-Home.h121199061.Hotel-Information)

Williamsburg

CA $135

CA $424 total

includes taxes & fees

Apr 18 - Apr 19

[](https://www.expedia.ca/Williamsburg-Hotels-Peaceful-Private-Pet-Friendly-Williamsburg-Home.h121199061.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-04-10&endDate=2026-04-11&regionId=8853&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Middlesboro%2C+Kentucky%2C+United+States+of+America&regionId=8853&latLong=36.608416%2C-83.716582&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=CABIN)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Middlesboro%2C+Kentucky%2C+United+States+of+America&regionId=8853&latLong=36.608416%2C-83.716582&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Middlesboro%2C+Kentucky%2C+United+States+of+America&regionId=8853&latLong=36.608416%2C-83.716582&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=COTTAGE)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Middlesboro%2C+Kentucky%2C+United+States+of+America&regionId=8853&latLong=36.608416%2C-83.716582&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=APARTMENT)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Middlesboro%2C+Kentucky%2C+United+States+of+America&regionId=8853&latLong=36.608416%2C-83.716582&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=HOUSE_BOAT)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Middlesboro%2C+Kentucky%2C+United+States+of+America&regionId=8853&latLong=36.608416%2C-83.716582&adults=2&startDate=2026-06-25&d1=2026-06-25&endDate=2026-06-28&d2=2026-06-28&lodging=VILLA)

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## Top Middlesboro Hotel Reviews

![Days Inn by Wyndham Jellico - Tennessee State Line](https://images.trvl-media.com/lodging/1000000/10000/300/279/ad47702e_y.jpg)

### Days Inn by Wyndham Jellico - Tennessee State Line

4/10 Poor

"Waited half an hour outside the hotel at 1:30am after driving 10 hours to wait for someone to unlock the lobby door and check us in. Then had to wait for the staff to find us a pet-free room even though we had pre-booked a pet-free room. It was noisy and we maybe got 2 hours of sleep. The breakfast was pretty scarce as well, even though we went at 6am as soon as it started. "

[](https://expedia.ca/Caryville-Hotels-Days-Inn-By-Wyndham-Jellico-Tennessee-State-Line.h279.Hotel-Information)

![Sleep Inn & Suites Middlesboro](https://images.trvl-media.com/lodging/4000000/3930000/3929600/3929546/86beaca2_y.jpg)

### Sleep Inn & Suites Middlesboro

10/10 Excellent

"The place was spotless.. nice rooms, the STAFF WAS AWESOME 😎.. when we arrived this older lady was at check-in, she was super helpful in knowing what is around the area and attractions.. we stayed all weekend.. would recommend.."

[](https://expedia.ca/Middlesboro-Hotels-Sleep-Inn-Suites.h3929546.Hotel-Information)

![Pine Mountain State Resort Park](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109434/75b8d155_y.jpg)

### Pine Mountain State Resort Park

10/10 Excellent

"This was an amazing experience !! Everything from the room to the staff and grounds were superb!!! We will definitely be returning to stay here it was so beautiful and relaxing !!!! "

[](https://expedia.ca/Corbin-Hotels-Pine-Mountain-State-Resort-Park.h1109434.Hotel-Information)

![Econo Lodge Middlesboro](https://images.trvl-media.com/lodging/1000000/20000/15200/15146/79102e17_y.jpg)

### Econo Lodge Middlesboro

8/10 Good

"There was plenty of parking and the beds were very comfortable."

[](https://expedia.ca/Middlesboro-Hotels-Econo-Lodge.h15146.Hotel-Information)

![Holiday Inn Express Middlesboro by IHG](https://images.trvl-media.com/lodging/1000000/70000/60900/60850/fba51913_y.jpg)

### Holiday Inn Express Middlesboro by IHG

10/10 Excellent

"There was a National Park close by And a lot of restaurants and Walmart"

[](https://expedia.ca/Middlesboro-Hotels-Holiday-Inn-Express-Middlesboro.h60850.Hotel-Information)

![Super 8 by Wyndham Williamsburg](https://images.trvl-media.com/lodging/1000000/10000/7000/6940/a5cd488f_y.jpg)

### Super 8 by Wyndham Williamsburg

2/10 Terrible

"Parking was, great nobody would go there"

[](https://expedia.ca/Corbin-Hotels-Super-8-By-Wyndham-Williamsburg.h6940.Hotel-Information)

![Quality Inn Harlan](https://images.trvl-media.com/lodging/1000000/20000/17000/16941/b003bff0_y.jpg)

### Quality Inn Harlan

10/10 Excellent

"Yes"

[](https://expedia.ca/Harlan-Hotels-Quality-Inn.h16941.Hotel-Information)

![Suburban Studios Middlesboro](https://images.trvl-media.com/lodging/70000000/69400000/69390100/69390006/4f60a168_y.jpg)

### Suburban Studios Middlesboro

10/10 Excellent

"This was one of the best rooms and hotels I have stayed at over the years. And for the price , you can't beat it. Appliances are all up to date, clean and perfect. They even supplied dish liquid to wash my own dishes if I needed to reuse them . Towels, cups and coffee we easily accessible. Staff was really nice and made my staff feel so wonderful on my Birthday weekend. Thanka to all the staff I interacted with who helped me in anyway, thanks for taking pride in your job and rooms and thanks for having me"

[](https://expedia.ca/Middlesboro-Hotels-Suburban-Extended-Stay-Hotel.h69390006.Hotel-Information)

![8BR Lakefront Lux Retreat: Private Dock, Sleeps 28](https://images.trvl-media.com/lodging/123000000/122380000/122378700/122378686/eb0930cb_y.jpg)

### 8BR Lakefront Lux Retreat: Private Dock, Sleeps 28

10/10 Excellent

"Great host very accommodating and responsive when needing info. The house with amazing and great viewsWill definitely be back here"

[](https://expedia.ca/Speedwell-Hotels-8BR-Lakefront-Lux-Retreat-Private-Dock.h122378686.Hotel-Information)

## Find out more about Middlesboro

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Middlesboro. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Vacation Homes in Middlesboro ](https://expedia.ca/Middlesboro-Private-Vacation-Homes.d8853-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cabin Rentals in Middlesboro ](https://expedia.ca/Middlesboro-Cabins.d8853-aaCabins.Travel-Guide-Accommodation)
- [Apartments in Middlesboro ](https://expedia.ca/Middlesboro-Apartments.d8853-aaApartments.Travel-Guide-Accommodation)
- [Houseboats in Middlesboro ](https://expedia.ca/Middlesboro-Houseboats.d8853-aaHouseboats.Travel-Guide-Accommodation)
- [Cottages in Middlesboro ](https://expedia.ca/Middlesboro-Cottages.d8853-aaCottages.Travel-Guide-Accommodation)
- [Motels in Middlesboro ](https://expedia.ca/Middlesboro-Motels.d8853-aaMotels.Travel-Guide-Accommodation)
- [Lodges in Middlesboro ](https://expedia.ca/Middlesboro-Lodges.d8853-aaLodges.Travel-Guide-Accommodation)
- [B&B in Middlesboro ](https://expedia.ca/Middlesboro-Bed-And-Breakfast.d8853-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Condo Rentals in Middlesboro ](https://expedia.ca/Middlesboro-Condos.d8853-aaCondos.Travel-Guide-Accommodation)

## Frequently asked questions

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