Middlesboro Vacation Rentals from AED 179: Search Short-Term Rentals

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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.

AED 1,239 total

includes taxes & fees

9 Nov - 10 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.

AED 1,174 total

includes taxes & fees

9 Nov - 10 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.

AED 1,389 total

includes taxes & fees

6 Nov - 7 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.

AED 1,372 total

includes taxes & fees

6 Nov - 7 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.

AED 1,363 total

includes taxes & fees

19 Nov - 20 Nov

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

Harrogate

Amy C.

AED 686 total

includes taxes & fees

7 Nov - 8 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.

AED 747 total

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.

AED 705 total

includes taxes & fees

19 Nov - 20 Nov

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.

AED 782 total

includes taxes & fees

29 Nov - 30 Nov

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.

AED 980 total

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

AED 329 total

includes taxes & fees

6 Nov - 7 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.

AED 1,047 total

includes taxes & fees

6 Nov - 7 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.

AED 1,077 total

includes taxes & fees

6 Nov - 7 Nov

A covered outdoor deck with wooden flooring and metal chairs.

14. Peaceful & Private! Pet-friendly Williamsburg Home

Williamsburg

AED 1,129 total

includes taxes & fees

6 Nov - 7 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.

AED 601 total

includes taxes & fees

8 Nov - 9 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

AED 920 total

includes taxes & fees

8 Nov - 9 Nov

17. Peaceful & Private! Pet-Friendly Williamsburg Home

Williamsburg

Alicia M.

AED 1,093 total

includes taxes & fees

6 Nov - 7 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.

AED 1,215 total

includes taxes & fees

6 Nov - 7 Nov

19. Outback Behind the Barn

Ewing

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

20. LMU Pine Mtn State Park Cumberland Gap Laurel Cove

Pineville

Hope C.

AED 1,213 total

includes taxes & fees

6 Dec - 7 Dec

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Find vacation rentals that suit your style

Top Middlesboro Hotel Reviews

A hotel entrance with a covered walkway, potted plants, and a reception area.

Holiday Inn Express Middlesboro by IHG

Middlesboro

10/10 Excellent

Anonymous traveler

A hotel room with a sofa, a coffee table, a bed with a canopy, a TV, and artwork on the walls.

Sleep Inn & Suites Middlesboro

Middlesboro

10/10 Excellent

Leonard

A Holiday Inn Express hotel with a parking lot and multiple vehicles.

Holiday Inn Express Williamsburg by IHG

Williamsburg

10/10 Excellent

The whole hotel was almost immaculately clean except for a few stray french fries I found in our room when I had to move one of our beds to get my kitten out from inside the frame. They are pet friendly as of recently because they haven't updated yet but you can't really tell they haven't updated yet as the hotel is so well taken care of. The staff was friendly and helpful. The beds were incredibly comfortable. Our bathroom door got stuck on the floor when opening and closing it but the shower...

Amanda

A hotel room with two single beds, a nightstand with a lamp, a small table, and a window with curtains.

Tazewell Motor Lodge

Tazewell

10/10 Excellent

happy traveler

A bedroom with a bed, a TV, a desk, and a chair.

Imperial Inn Tazewell

Tazewell

10/10 Excellent

Linda

A hotel room with a large bed, two bedside tables with lamps, a desk with a chair, a television, and a bathroom visible through an open door.

Suburban Studios Middlesboro

Middlesboro

10/10 Excellent

Kim

A hotel room with two beds, a desk, a chair, a lamp, and artwork on the walls.

Quality Inn

Barbourville

10/10 Excellent

Betsy

A white portable air conditioner mounted on a wall with a control panel, a power outlet, and a plastic bag hanging from the bottom.

Boone Trail Inn

Middlesboro

10/10 Excellent

Josh

A hotel room with two beds, a nightstand, a lamp, a phone, and a sunset mural on the wall.

Days Inn by Wyndham Jellico - Tennessee State Line

Jellico

10/10 Excellent

Denise

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.

Middlesboro Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Middlesboro vacation 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 vacation rentals that suit your style

Top Middlesboro Hotel Reviews

Holiday Inn Express Middlesboro by IHG

10/10 Excellent

Frequently Asked Questions

Are there vacation rentals in Middlesboro?

What's the top vacation rental that Middlesboro has to offer?

How many vacation rentals are there in Middlesboro?

What’s there to see and do in Middlesboro?

What’s a vacation rental in Middlesboro like?