Middlesboro Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Middlesboro holiday rentals

4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,

4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
Middlesboro
10.0 out of 10, Exceptional, (33 reviews)
"Very nice and extra clean great time"
United States
Johnny C.
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,

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.
Middlesboro
9.2 out of 10, Wonderful, (5 reviews)
"We enjoyed our stay. "
United States
Emily S.
The price is NZ$582
includes taxes & fees
12 May - 13 May
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
Middlesboro
The price is NZ$473
includes taxes & fees
11 May - 12 May
Private bungalow close to LMU, ARH, Cumberland Gap

Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU

Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
Middlesboro
10.0 out of 10, Exceptional, (1 review)
"Clean"
United States
Phineas S.
The price is NZ$621
includes taxes & fees
28 May - 29 May
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU

Welcoming 3-bedroom house with AC in charming Middlesboro

Welcoming 3-bedroom house with AC in charming Middlesboro
Middlesboro
7.0 out of 10, Good, (2 reviews)
"Great area to stay in "
United States
Corinna E.
The price is NZ$576
includes taxes & fees
27 May - 28 May
Welcoming 3-bedroom house with AC in charming Middlesboro

Outback Behind the Barn

Outback Behind the Barn
Ewing
The price is NZ$229
includes taxes & fees
20 May - 21 May
Outback Behind the Barn

RV/Camper Sites. No Electric

RV/Camper Sites. No Electric
Speedwell
The price is NZ$107
includes taxes & fees
10 May - 11 May
RV/Camper Sites. No Electric

Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!

Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
Tazewell
9.2 out of 10, Wonderful, (9 reviews)
"We had a great stay. Everything was perfect. Would recommend this place to anyone visiting the area. "
United States
Tim D.
The price is NZ$291
includes taxes & fees
11 May - 12 May
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!

Robertson Ridge Hideaway Cottage

Robertson Ridge Hideaway Cottage
Hinkle
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful place "
United States
Isaac L.
The price is NZ$245
includes taxes & fees
10 May - 11 May
Robertson Ridge Hideaway Cottage

Harrogate Hideaway - 5 Min to LMU & Nat`l Park

Harrogate Hideaway - 5 Min to LMU & Nat`l Park
Harrogate
9.8 out of 10, Exceptional, (16 reviews)
"Harrogate Hideaway was a very clean and cute place to stay. We really enjoyed our time here. Our host Ciara was great!"
United States
Carla P.
The price is NZ$323
includes taxes & fees
12 May - 13 May
Harrogate Hideaway - 5 Min to LMU & Nat`l Park

Calm Country Oasis - Creek, ATV Trls & Norris Lake

Calm Country Oasis - Creek, ATV Trls & Norris Lake
Speedwell
9.6 out of 10, Exceptional, (24 reviews)
"We had a wonderful weekend:)"
United States
Bobbi F.
The price is NZ$433
includes taxes & fees
13 May - 14 May
Calm Country Oasis - Creek, ATV Trls & Norris Lake

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Cumberland Gap
9.2 out of 10, Wonderful, (46 reviews)
"Cozy place perfect for what we needed. "
United States
Emily N.
The price is NZ$360
includes taxes & fees
20 May - 21 May
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Beautiful Loft in the Woods

Beautiful Loft in the Woods
Harlan
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful setting. Incredible space well laid out. Owner was very engaging. "
United States
Fred
The price is NZ$427
includes taxes & fees
10 May - 11 May
Beautiful Loft in the Woods

Blissful Bungalow across from LMU campus

Blissful Bungalow across from LMU campus
Harrogate
9.6 out of 10, Exceptional, (34 reviews)
"Very convenient to everything we needed to do, very clean and neat"
United States
Brandi L.
The price is NZ$370
includes taxes & fees
17 May - 18 May
Blissful Bungalow across from LMU campus

Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina

Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
Speedwell
9.4 out of 10, Exceptional, (20 reviews)
"Cute and cozy! Perfect place for us to use as a home base while in town visiting family. Lots of attention to the details, kitchen facilities are up to date and super clean. Already looking forward to booking again!"
United States
Lynette M.
The price is NZ$303
includes taxes & fees
21 May - 22 May
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina

Harrogate Home Mountain View’s Dog Friendly

Harrogate Home Mountain View’s Dog Friendly
Harrogate
10.0 out of 10, Exceptional, (25 reviews)
"Great location with friendly neighbors!"
United States
Evan C.
The price is NZ$453
includes taxes & fees
10 May - 11 May
Harrogate Home Mountain View’s Dog Friendly

Quaint Studio APT Near ATV Trails & Norris Lake

Quaint Studio APT Near ATV Trails & Norris Lake
LaFollette
9.6 out of 10, Exceptional, (11 reviews)
"Check in was very easy amazing little place. Loved the mornings going out to the porch and hearing the birds chirping. Definitely coming back and staying again "
United States
Melisza
The price is NZ$228
includes taxes & fees
31 May - 1 June
Quaint Studio APT Near ATV Trails & Norris Lake

Charming 3-bedroom house with WiFi, AC in Pineville Kentucky

Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Pineville
10.0 out of 10, Exceptional, (4 reviews)
"clean house very beautiful, host was amazing, scenery stunning. "
United States
Evelyn B.
The price is NZ$469
includes taxes & fees
11 May - 12 May
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Middlesboro Hotel Reviews

Find out more about Middlesboro

Everything you need to know about Middlesboro holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middlesboro holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Middlesboro holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlesboro holiday rentals we have selected for you start as low as NZ$286 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 holiday 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 holiday.

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. 

Frequently asked questions

Are there holiday rentals in Middlesboro?

Yes, there are holiday rentals close to the most popular sights in Middlesboro, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that Middlesboro has to offer?

Beautiful Norris Lake Front A-Frame with Private Dock in Speedwell, TN: This holiday home rental outside of Middlesboro is located on a lake, and has a balcony, a selection of games and a BBQ 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 that you can cook with friends or family.

How many holiday rentals are there in Middlesboro?

With 6 Expedia holiday rentals, you're guaranteed 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 Mall and Cumberland Gap National Historical Park are other places worth a visit.

What’s a holiday rental in Middlesboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middlesboro. Holiday rentals feature amenities such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for families.