mountain view

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

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$607
includes taxes & fees
24 June - 25 June
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$512
includes taxes & fees
7 July - 8 July
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
Middlesboro
8.0 out of 10, Very good, (3 reviews)
"Great area to stay in "
United States
Corinna E.
The price is NZ$617
includes taxes & fees
23 July - 24 July
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
Middlesboro
7.4 out of 10, Good, (3 reviews)
"Advertised would sleep 12, yes it had beds for 12, but I guess we were to share towels , could be cleaner, food and trash under sofa cushions. Had to hunt for the WiFi password."
United States
Elita W.
The price is NZ$715
includes taxes & fees
23 July - 24 July
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
Speedwell
Modern 20’ Travel Trailer with bunks and a queen bed

The Nomad on Norris Lake

The Nomad on Norris Lake
New Tazewell
The price is NZ$658
includes taxes & fees
6 July - 7 July
The Nomad on Norris Lake

One Bedroom Rustic Cabin

One Bedroom Rustic Cabin
Speedwell
The price is NZ$171
includes taxes & fees
24 June - 25 June
One Bedroom Rustic Cabin

Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home
3.0 star property
Williamsburg
The price is NZ$537
includes taxes & fees
24 June - 25 June
Peaceful & Private! Pet-friendly Williamsburg Home

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$256
includes taxes & fees
25 June - 26 June
Robertson Ridge Hideaway Cottage

Blissful Bungalow across from LMU campus

Blissful Bungalow across from LMU campus
Harrogate
9.6 out of 10, Exceptional, (36 reviews)
"Very convenient to everything we needed to do, very clean and neat"
United States
Brandi L.
The price is NZ$452
includes taxes & fees
25 June - 26 June
Blissful Bungalow across from LMU campus

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$251
includes taxes & fees
8 July - 9 July
Quaint Studio APT Near ATV Trails & Norris Lake

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, (22 reviews)
"Was in a great location to be able to go to multiple riding locations. "
United States
Sara R.
The price is NZ$297
includes taxes & fees
25 June - 26 June
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina

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, (11 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$314
includes taxes & fees
6 July - 7 July
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!

Remodeled Western Country Getaway Near Lake & Trails

Remodeled Western Country Getaway Near Lake & Trails
LaFollette
10.0 out of 10, Exceptional, (1 review)
"Very clean and nice apartment. Just as advertised. Had everything we needed and we were very pleased. Great place! You will not be disappointed. We will definitely be going back!"
United States
Gregory T.
The price is NZ$311
includes taxes & fees
6 July - 7 July
Remodeled Western Country Getaway Near Lake & Trails

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)
"Property is great for access to trails for SxS and the property it beautiful. You can have a bomb fire or enjoy the water. We loved it."
United States
Colt L.
The price is NZ$485
includes taxes & fees
24 June - 25 June
Calm Country Oasis - Creek, ATV Trls & Norris Lake

Peaceful & Private! Pet-Friendly Williamsburg Home

Peaceful & Private! Pet-Friendly Williamsburg Home
Williamsburg
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful peaceful setting, great views! Host was very nice and helpful! Home was very clean and comfortable. Pet friendly, and kid friendly :)Highly recommend!"
United States
Alicia M.
The price is NZ$532
includes taxes & fees
24 June - 25 June
Peaceful & Private! Pet-Friendly Williamsburg Home

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$477
includes taxes & fees
29 June - 30 June
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

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)
"Such a cute little apartment! It had everything we needed for our stay. "
United States
Cindy
The price is NZ$388
includes taxes & fees
29 June - 30 June
Harrogate Hideaway - 5 Min to LMU & Nat`l Park

Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's

Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's
Sharps Chapel
10.0 out of 10, Exceptional, (6 reviews)
"This was definitely the most romantic VRBO we’ve stayed at!!! Very clean, and the view from all of the balconies was incredible!!! "
United States
Stan N.
The price is NZ$535
includes taxes & fees
24 June - 25 June
Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's

The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!

The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!
Pineville
9.6 out of 10, Exceptional, (5 reviews)
"The home was just perfect for what we needed. Looking forward to seeing how it comes out when all construction is finished! Host was very responsive. Will stay again"
United States
Kami L.
The price is NZ$646
includes taxes & fees
25 June - 26 June
The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!
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$395 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. 

Explore a world of travel with Expedia

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?

Lake Front 2-Bedroom Home W/ Privacy! Beautiful Views & Numerous Amenities...: This holiday home rental outside of Middlesboro is located on a lake, and has a patio, a private garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

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, Cumberland Gap National Historical Park and Middlesboro Country Club 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.