Photo by Alexis Wyrick

Middlesboro Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

This weekend
Next weekend

Our top choices for Middlesboro vacation rentals

10.0 out of 10, Exceptional, (23)
"Very nice and extra clean great time"
United States
Johnny C.
$210 nightly
The price is $232
Jan 2 - Jan 3, 2026
Total with taxes and fees
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
9.2 out of 10, Wonderful, (5)
"We enjoyed our stay. "
United States
Emily S.
$337 nightly
The price is $372
Jan 1 - Jan 2, 2026
Total with taxes and fees
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
10.0 out of 10, Exceptional, (1)
"Clean"
United States
Phineas S.
$302 nightly
The price is $333
Jan 21 - Jan 22, 2026
Total with taxes and fees
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
$255 nightly
The price is $281
Jan 25 - Jan 26, 2026
Total with taxes and fees
Welcoming 3-bedroom house with AC in charming Middlesboro
2.0 star property
$115 nightly
The price is $127
Jan 1 - Jan 2, 2026
Total with taxes and fees
Modern 20’ Travel Trailer with bunks and a queen bed

Camping in Speedwell

RV/Camper Sites. No Electric
2.0 star property
$65 nightly
The price is $71
Jan 5 - Jan 6, 2026
Total with taxes and fees
RV/Camper Sites. No Electric
10.0 out of 10, Exceptional, (4)
"Everything was clean and felt like home.host was really nice and I will definitely be staying again."
United States
Nicholas H.
$146 nightly
The price is $161
Jan 4 - Jan 5, 2026
Total with taxes and fees
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!

Apartment in Harlan

Beautiful Loft in the Woods
10.0 out of 10, Exceptional, (3)
"Beautiful setting. Incredible space well laid out. Owner was very engaging. "
United States
Fred
$211 nightly
The price is $233
Jan 1 - Jan 2, 2026
Total with taxes and fees
Beautiful Loft in the Woods
9.2 out of 10, Wonderful, (42)
"Great location. Easy walk to town and close to hiking areas. Highly recommend. "
United States
Linda O.
$189 nightly
The price is $211
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
3.0 star property
$278 nightly
The price is $307
Jan 1 - Jan 2, 2026
Total with taxes and fees
Peaceful & Private! Pet-friendly Williamsburg Home
2.0 star property
10.0 out of 10, Exceptional, (2)
"The cabin was clean, cozy, and overall amazing! "
United States
Fannie
$186 nightly
The price is $206
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Highlands Cabin Retreat at Norris Lake

Cabin in Speedwell

One Bedroom Rustic Cabin
2.0 star property
$79 nightly
The price is $86
Jan 1 - Jan 2, 2026
Total with taxes and fees
One Bedroom Rustic Cabin
9.6 out of 10, Exceptional, (25)
"This place was just as described and perfect for our stay!"
United States
Melissa M.
$178 nightly
The price is $199
Jan 4 - Jan 5, 2026
Total with taxes and fees
Luxury Brooklyn St APT - Near LMU & Nat’l Park
10.0 out of 10, Exceptional, (22)
"Great location with friendly neighbors!"
United States
Evan C.
$263 nightly
The price is $300
Jan 3 - Jan 4, 2026
Total with taxes and fees
Harrogate Home Mountain View’s Dog Friendly
9.4 out of 10, Exceptional, (19)
"It was exceptional "
United States
Dennis W.
$124 nightly
The price is $139
Jan 5 - Jan 6, 2026
Total with taxes and fees
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
9.0 out of 10, Wonderful, (2)
"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.
$294 nightly
The price is $325
Jan 21 - Jan 22, 2026
Total with taxes and fees
The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!
2.0 star property
$276 nightly
The price is $302
Jan 1 - Jan 2, 2026
Total with taxes and fees
Peaceful & Private! Pet-Friendly Williamsburg Home
10.0 out of 10, Exceptional, (2)
"We stayed here for a wedding weekend in Pineville, KY, and it was absolutely perfect from start to finish. The home was spotless, cozy, and had everything we could possibly need. The beds were so comfortable, and we instantly felt at home the moment we walked in.What truly set this stay apart was the host’s kindness and above-and-beyond hospitality. We got lost in the middle of the night trying to find the property, and the host stayed on the phone with us, patiently guiding us right to the...
United States
Samantha P.
$268 nightly
The price is $296
Jan 1 - Jan 2, 2026
Total with taxes and fees
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
10.0 out of 10, Exceptional, (5)
"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.
$263 nightly
The price is $296
Jan 19 - Jan 20, 2026
Total with taxes and fees
Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's
$166 nightly
The price is $183
Jan 27 - Jan 28, 2026
Total with taxes and fees
2-bedroom apartment in adorable Pineville with AC for relaxing stays
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 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 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.

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?

8BR Lakefront Lux Retreat: Private Dock, Sleeps 28: This vacation home near Middlesboro is located on a lake and has a fireplace, an arcade game room, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a hot tub.

How many vacation rentals are there in Middlesboro?

With 5 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?

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 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.