Middlesboro Vacation Rentals from CA $250: Short-Term Rentals for 2026

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Our top choices for Middlesboro vacation rentals

A living room with a stone fireplace, wooden walls, a sofa, a coffee table, and a TV mounted on the wall.

1. Gorgeous 4-bedroom house in Middlesboro KY with WiFi, AC. Minutes from LMU

Middlesboro

Konnie D.

CA $538 total

includes taxes & fees

Nov 19 - Nov 20

A bedroom with a bed, pillows, a nightstand, a lamp, a window with blinds, and a kitchen area with a refrigerator.

2. Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

Middlesboro

Emily S.

CA $428 total

includes taxes & fees

Nov 19 - Nov 20

A brick house with a covered porch, a front door, and a small garden area with potted plants.

3. Welcoming 3-bedroom house with AC in charming Middlesboro

Middlesboro

Corinna E.

CA $476 total

includes taxes & fees

Nov 16 - Nov 17

A dining area with a table set for four, a ceiling fan, and a sign above reading 'BE OUR GUEST'.

4. Private bungalow close to LMU, ARH, Cumberland Gap

Middlesboro

Leann L.

CA $440 total

includes taxes & fees

Nov 16 - Nov 17

A living room with a TV on a wooden stand, a white chair, a small table, and a sofa.

5. House close to ARH Hospital, Tackett Creek & LMU!

Middlesboro

Elita W.

CA $437 total

includes taxes & fees

Dec 15 - Dec 16

A single-story house with a porch, a mailbox, and a small garden.

6. Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cumberland Gap

JOHN H.

CA $290 total

includes taxes & fees

Nov 19 - Nov 20

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

Harrogate

Amy C.

CA $263 total

includes taxes & fees

Nov 16 - Nov 17

An aerial view of a campus with multiple buildings, a central tower, and a large open grassy area.

8. Blissful Bungalow across from LMU campus

Harrogate

Eva M.

CA $307 total

includes taxes & fees

Nov 19 - Nov 20

A rustic wooden building with a porch, stone pillars, and potted plants.

9. Luxury Brooklyn St APT - Near LMU & Nat’l Park

Cumberland Gap

Theresa l.

CA $275 total

includes taxes & fees

Nov 23 - Nov 24

A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a sign reading "EVERYDAY COOKING".

10. Harrogate Home Mountain View’s Dog Friendly

Harrogate

Jodi D.

CA $424 total

includes taxes & fees

Nov 17 - Nov 18

A wooden deck with a railing, a brick building, and a door with a window.

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

Pineville

seth r.

CA $419 total

includes taxes & fees

Nov 20 - Nov 21

A room with a large window offering a view of a well-maintained garden with trees and grass.

12. Calm Country Oasis - Creek, ATV Trls & Norris Lake

Speedwell

Sandra

CA $359 total

includes taxes & fees

Nov 16 - Nov 17

An outdoor patio with a wooden table and wicker chairs.

13. Park Ave Laurel Cove, Bell Theatre & LMU

Pineville

Cassie S.

CA $494 total

includes taxes & fees

Nov 16 - Nov 17

A covered outdoor deck with wooden flooring and metal chairs.

Barbourville

Jackson H.

CA $377 total

includes taxes & fees

Nov 16 - Nov 17

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Top Middlesboro Hotel Reviews

Pine Mountain State Resort Park

10/10 Excellent

"Great stay for nature lovers. Balcony nice feature."

Econo Lodge Middlesboro

10/10 Excellent

"Soon as we arrived, we were met by Susan who worked inside. ..so friendly ,helpful ,..such a warm welcoming and that’s the beginning of an awesome stay ..we made coffeees (delicious) and she gave us some snacks ..room was awesome and clean as a whistle ..breakfast was delicious ..just go you won’t be disappointed..Susan thanks for the directions to the mountain it was breathtaking .."

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

10/10 Excellent

"It was a very nice and beautiful place. We rented it because we got married on Saturday and we need a place for the family to stay and believe it or not. This once belonged to one of my really good friends. This place did back years ago"

Book your fall retreat today!!! Lake all day and fire at night.

10/10 Excellent

"Large family (19 people) vacation was wonderful, plenty of space for all the ages in our group. Spaces for everyone in the house for quiet time or gathering. House came with more than enough kitchen supplies to create meals for our group , games, puzzles, ping pong, cornhole. The walk to the dock was the only troublesome thing,one of our family members was not able to walk it, everyone else managed to the dock swam, kayaked, played on floating mat, fished, had an enjoyable experience. Luckily for October weather was fabulous only 1 rainy day and was warm enough temps and lake temp to swim. Definitely would recommend this home. Owner was easy to contact and answered promptly."

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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlesboro vacation rentals we have selected for you start as low as CA $250 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 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?

Brand New, Spacious 9 bedroom, 9 1/2 bath Waterfront house in Lakeside Estates: This vacation home rental near Middlesboro offers a patio, a hot tub, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 9 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Middlesboro?

With 6 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.

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Our top choices for Middlesboro vacation rentals

1. Gorgeous 4-bedroom house in Middlesboro KY with WiFi, AC. Minutes from LMU

2. Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

3. Welcoming 3-bedroom house with AC in charming Middlesboro

4. Private bungalow close to LMU, ARH, Cumberland Gap

5. House close to ARH Hospital, Tackett Creek & LMU!

6. Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

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

8. Blissful Bungalow across from LMU campus

9. Luxury Brooklyn St APT - Near LMU & Nat’l Park

10. Harrogate Home Mountain View’s Dog Friendly

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

12. Calm Country Oasis - Creek, ATV Trls & Norris Lake

13. Park Ave Laurel Cove, Bell Theatre & LMU

14. Peaceful & Private! Pet-friendly Williamsburg Home

15. 2-bedroom loft apartment in adorable Pineville close to Pine Mountain State Park

16. LMU Pine Mtn State Park Cumberland Gap Laurel Cove

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

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

19. Peaceful & Private! Pet-Friendly Williamsburg Home

20. Welcome to The Classic Corner—a freshly renovated unique apartment.

Find vacation rentals that suit your style

Top Middlesboro Hotel Reviews

Pine Mountain State Resort Park

Imperial Inn Tazewell

Sleep Inn & Suites Middlesboro

Suburban Studios Middlesboro

Econo Lodge Middlesboro

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

Serene cabin with dock/swim platform in charming Speedwell

Book your fall retreat today!!! Lake all day and fire at night.

Beautiful Lakefront Getaway - Sleeps 26 - Norris Lake’s Best Location

Find out more about Middlesboro

Frequently asked questions

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