Middlesboro Holiday Rentals from AU$249: Search Short-Term Rentals

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Our top choices for Middlesboro holiday 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.

includes taxes & fees

4 Nov - 5 Nov

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

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

Middlesboro

Leann L.

includes taxes & fees

4 Nov - 5 Nov

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

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

Middlesboro

Emily S.

includes taxes & fees

4 Nov - 5 Nov

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

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

Middlesboro

Corinna E.

includes taxes & fees

4 Nov - 5 Nov

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.

includes taxes & fees

19 Nov - 20 Nov

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

Harrogate

Amy C.

includes taxes & fees

4 Nov - 5 Nov

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

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

Cumberland Gap

JOHN H.

includes taxes & fees

19 Nov - 20 Nov

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

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

Cumberland Gap

Theresa l.

includes taxes & fees

4 Dec - 5 Dec

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

9. Blissful Bungalow across from LMU campus

Harrogate

Brandi L.

includes taxes & fees

4 Dec - 5 Dec

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.

includes taxes & fees

9 Nov - 10 Nov

A long, narrow hallway with exposed wooden beams and a concrete floor. There is a door on the right and a window on the left.

11. One Bedroom Rustic Cabin

Speedwell

includes taxes & fees

15 Nov - 16 Nov

A dining area with a wooden table set for four, a lamp, and framed artwork on the walls.

12. 2-bedroom loft apartment in adorable Pineville close to Pine Mountain State Park

Pineville

jennifer w.

includes taxes & fees

15 Nov - 16 Nov

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

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

Pineville

seth r.

includes taxes & fees

15 Nov - 16 Nov

A covered outdoor deck with wooden flooring and metal chairs.

14. Peaceful & Private! Pet-friendly Williamsburg Home

Williamsburg

includes taxes & fees

15 Nov - 16 Nov

A wooden deck with a rocking chair and a wicker sofa.

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

Tazewell

Carla C.

includes taxes & fees

15 Nov - 16 Nov

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

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

Speedwell

Sandra

includes taxes & fees

15 Nov - 16 Nov

17. Peaceful & Private! Pet-Friendly Williamsburg Home

Williamsburg

Alicia M.

includes taxes & fees

4 Nov - 5 Nov

A spacious living room with wooden beams, leather sofas, a wooden coffee table, and a mounted deer head.

18. Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg

Williamsburg

Nancy A.

includes taxes & fees

4 Nov - 5 Nov

19. Outback Behind the Barn

Ewing

includes taxes & fees

15 Nov - 16 Nov

A covered outdoor seating area with a sofa, chairs, and planters.

20. LMU Pine Mtn State Park Cumberland Gap Laurel Cove

Pineville

Hope C.

includes taxes & fees

5 Nov - 6 Nov

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Top Middlesboro Hotel Reviews

Suburban Studios Middlesboro

10/10 Excellent

"Perfect for quick night’s stay. Clean, quiet, and convenient to LMU and Cumberland Gap Park. The continental breakfast was basic but good- I only eat light breakfast always. People were very nice."

Holiday Inn Express Williamsburg by IHG

8/10 Good

"The location of this property is very good and easy to access. Room was spacious and well-equipped except for a coffee maker. Our room happened to be just above the roof top for the front entrance leaving an unattractive view. Also, the darker shade on the window would not close leaving the room well-lit all night from bright lights outside. And cars turning at an intersection not far away had their headlights aimed directly at the window, which was a little annoying. The best part of our stay was the breakfast. It provided a very good variety and was being added to frequently."

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."

Floating Holiday #4 on Norris Lake at Springs Dock Marina. Front Row View!

10/10 Excellent

"We had a marvelous stay in Floating Holiday 4. The house was exactly as described in the listing. We were very happy with the selection of dishes, bowls, pots and pans and supplies. It had plenty of everything we could have wanted. The view from the front porch is outstanding. You could not have asked for a more wonderful lake vacation. Mary is a wonderful hostess. She provides all of the information you need ahead of time. She checked on us at arrival and during our stay just to make sure we didn’t need anything and that we were happy with everything. We loved our stay!!"

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 favourite 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 depend 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 AU$249 per night. Entering your travel dates in the search wizard might find you 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?

Brand New, Spacious 9 bedroom, 9 1/2 bath Waterfront house in Lakeside Estates: This holiday home rental outside of Middlesboro offers a patio, 1 hot tub and a BBQ 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 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.

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Check prices for these dates

Our top choices for Middlesboro holiday rentals

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

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

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

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

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

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

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

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

9. Blissful Bungalow across from LMU campus

10. Harrogate Home Mountain View’s Dog Friendly

11. One Bedroom Rustic Cabin

12. 2-bedroom loft apartment in adorable Pineville close to Pine Mountain State Park

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

14. Peaceful & Private! Pet-friendly Williamsburg Home

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

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

17. Peaceful & Private! Pet-Friendly Williamsburg Home

18. Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg

19. Outback Behind the Barn

20. LMU Pine Mtn State Park Cumberland Gap Laurel Cove

Find holiday rentals that suit your style

Top Middlesboro Hotel Reviews

Suburban Studios Middlesboro

Imperial Inn Tazewell

Pine Mountain State Resort Park

Sleep Inn & Suites Middlesboro

Holiday Inn Express Williamsburg by IHG

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

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

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

Floating Holiday #4 on Norris Lake at Springs Dock Marina. Front Row View!

Find out more about Middlesboro

Frequently asked questions

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