
Middlesboro Vacation Rentals
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Our top choices for Middlesboro vacation rentals

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.
Private bungalow close to LMU, ARH, Cumberland Gap
Private bungalow close to LMU, ARH, Cumberland Gap
Welcoming 3-bedroom house with AC in charming Middlesboro
Welcoming 3-bedroom house with AC in charming Middlesboro
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
Modern 20’ Travel Trailer with bunks and a queen bed
Modern 20’ Travel Trailer with bunks and a queen bed
Peaceful & Private! Pet-friendly Williamsburg Home
Peaceful & Private! Pet-friendly Williamsburg HomeFind vacation rentals that suit your style
Top Middlesboro Hotel Reviews

Super 8 by Wyndham Williamsburg
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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Middlesboro in high season.
Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $225 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.
Explore a world of travel with Expedia
- Hotels near Middlesboro Mall
- Hotels near The Pinnacle
- Hotels near Wasioto Winds Golf Course
- Hotels near Pine Mountain State Resort Park
- Calvin Hotels
- Motels in Calvin
- Laurel Lakes Hotels
- Pineville Hotels
- Cabin Rentals in Pineville
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- Williamsburg Hotels
- Grays Knob Hotels
- Loyall Hotels
- Cabin Rentals in Loyall
- Cabin Rentals in Williamsburg
- Pet-Friendly Hotels in Williamsburg
- Motels in Williamsburg
- Hotels with Restaurants in Williamsburg
- Bell County Historical Society Museum
- Middlesboro Mall
- Wasioto Winds Golf Course
- Pine Mountain State Resort Park
- Visit Calvin
- Visit Pineville
- Visit Frakes
- Visit Artemus
- Visit Bryants Store
- Visit Bimble
- Bimble Vacations
- Dr Thomas Walker State Park
- Visit Barbourville
- Visit Stoney Fork
- Visit Heidrick
- Visit Coldiron
- Visit Wallins Creek
- Wallins Creek Vacations
- Visit Girdler
- Visit Grays Knob
- Visit Loyall
- Visit Williamsburg
- Car rentals near Calvin
- Car rentals near Laurel Lakes
- Car rentals near Pineville
- Car rentals near Frakes
- Car rentals near Artemus
- Car rentals near Bryants Store
- Car rentals near Bimble
- Car rentals near Barbourville
- Hertz Rental Cars in Barbourville
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- Car rentals near Pleasant View
- Car rentals near Grays Knob
- Car rentals near Loyall
- Car rentals near Williamsburg

















































































