Middlesboro Holiday Rentals, Kentucky: Private House Rentals

An aerial view of a town surrounded by mountains, with a mix of residential and commercial buildings, and a highway running through the center.

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Our top choices for Middlesboro hotels

A hotel room with two beds, a sofa, a nightstand with a lamp, and a framed picture on the wall.

A reception area with a striped armchair, a counter, and a view of the parking lot through glass doors.

A hotel entrance with a covered lobby area, a clear sky, and a parking lot with cars.

A vending machine with snacks and a Scotsman branded water dispenser.

1. Econo Lodge Middlesboro

Middlesboro

Myung

2.316.600 ₫

2.553.820 ₫ total

includes taxes & fees

1 Oct - 2 Oct

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

A Sleep Inn & Suites building with a covered entrance, stone pillars, and a clear blue sky.

A hotel reception area with a counter, coffee machines, a fruit juice dispenser, and a refrigerator.

A reception area with a wooden reception desk, a glass partition, and a small round table with a decorative centerpiece.

2. Sleep Inn & Suites Middlesboro

Middlesboro

Joleen

2.850.900 ₫

3.197.952 ₫ total

includes taxes & fees

18 Oct - 19 Oct

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

A sign for Boone Trail Inn with a directional arrow.

A hotel room with a large bed, two bedside lamps, a nightstand, a chair, and a painting on the wall.

A motel with a two-story structure, a parking lot, and a stone wall.

3. Boone Trail Inn

Middlesboro

Nicola

2.111.850 ₫

2.786.700 ₫ total

includes taxes & fees

25 Sept - 26 Sept

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.

A modern kitchen with wooden cabinets, a white countertop, a built-in microwave, and a refrigerator.

A restaurant with striped chairs, a wooden counter, and a chandelier.

A vending machine with snacks and a water dispenser in a commercial setting.

4. Suburban Studios Middlesboro

Middlesboro

Clinton

1.990.560 ₫

2.194.394 ₫ total

includes taxes & fees

19 Oct - 20 Oct

A bed with white bedding and pillows against a wooden headboard.

A hotel with a gas station, a flag, and well-maintained landscaping.

A coffee station with two coffee machines and a variety of coffee pods and cups.

A hotel room with a blue sofa, a dark armchair, a small desk, and a dining table with chairs.

5. Holiday Inn Express Middlesboro by IHG

Middlesboro

"We had a wonderful stay at the Holiday Inn Express in Middlesboro, KY. The staff truly made our visit special—they were incredibly pleasant, helpful, and always made sure all of our needs were met. Every single day, we were greeted with warm smiles and friendly faces. They even went out of their way to give us excellent local recommendations for dinner. Their outstanding customer service made us feel right at home. We highly recommend this hotel to anyone visiting the area!"

Tolly

3.614.000 ₫

3.983.980 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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

A modern bathroom with a glass-enclosed shower, a toilet, a sink, and a small wooden stool.

A motel with a central staircase, multiple balconies, and a parking lot.

A covered outdoor area with a brick wall, benches, and a parking lot in the background.

6. Imperial Inn Tazewell

Tazewell

Karen

1.909.960 ₫

2.220.140 ₫ total

includes taxes & fees

8 Oct - 9 Oct

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

A modern living room with a blue sofa, a round coffee table, and a statue. There is a TV mounted on the wall and a window with a view of greenery outside.

A multi-story hotel with a brick facade, green balconies, and numbered doors.

A multi-story hotel with a swimming pool, outdoor seating, and a forested backdrop.

7. Days Inn by Wyndham Jellico - Tennessee State Line

Jellico

Surbhi

1.534.000 ₫

1.752.595 ₫ total

includes taxes & fees

27 Sept - 28 Sept

A hotel entrance with a covered parking area, stone pillars, and a blue-lit facade.

A hotel room with a coffee machine, a bed, and a window with a view.

8. Holiday Inn Express Williamsburg by IHG

Williamsburg

Christy

3.068.000 ₫

3.414.684 ₫ total

includes taxes & fees

20 Oct - 21 Oct

A park with green benches, a basketball hoop, and a paved area.

A room with a wooden dresser, a flat-screen TV mounted on the wall, a small black refrigerator, and a wall-mounted mirror.

A hotel with a signboard reading "Dixie Plaza Hotel Office".

A hotel room with two beds, a desk, a TV, and a bathroom.

9. Dixie Plaza hotel

Tazewell

Timothy

1.642.680 ₫

1.909.615 ₫ total

includes taxes & fees

25 Sept - 26 Sept

A home office with a desk, computer, and chair. There are two framed pictures on the wall, a window with an American flag, and a view of a pool outside.

A room with a wooden cabinet, a flat-screen TV, and a coffee machine.

A hotel room with a bed, desk, TV, microwave, refrigerator, chair, and a painting on the wall.

A modern dining area with tables and chairs, a kitchen counter, and a large window offering a view of the outdoors.

10. Quality Inn

Barbourville

"Over all it wasn’t a horrible stay if you’re just passing through. We got there alittle after midnight and were checked out by 930. Rooms were pretty clean all though there was a weird smell. Beds were kind of small but decent. The only complaint we have is the car alarm going off multiple times in the night then the kids running around outside yelling setting off the alarms again at 630 in the morning right outside our room.."

Dustina

2.652.000 ₫

3.007.898 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A natural setting with a clear pond surrounded by rocks and trees, and rows of blue chairs arranged for an event.

A picnic table and stone wall in a forested area with a view of distant mountains.

A rustic interior with wooden beams, a fireplace, and a bar area.

A rustic interior with wooden beams, leather sofas, rocking chairs, and a bar area.

11. Pine Mountain State Resort Park

Pineville

marie and steve

3.118.700 ₫

3.438.240 ₫ total

includes taxes & fees

12 Oct - 13 Oct

A row of white planters with red and purple flowers along a brick wall.

A hotel room with a large bed, two bedside tables, a nightstand, a sofa, a window with curtains, and a wall-mounted picture.

A modern living room with a fireplace, two sofas, a coffee table, and a flat-screen TV mounted on the wall.

A restaurant with a counter displaying various food items and a seating area with tables and chairs.

12. Quality Inn Harlan

Harlan

Rhett

2.267.200 ₫

2.571.458 ₫ total

includes taxes & fees

18 Oct - 19 Oct

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

A corridor with benches, doors, and an exit sign.

A motel with a red roof, a parking lot, and a signboard.

A bathroom with a bathtub, a shower curtain, and a toilet.

13. Tazewell Motor Lodge

Tazewell

laura

1.635.140 ₫

2.203.240 ₫ total

includes taxes & fees

14 Oct - 15 Oct

An aerial view of a golf course with multiple ponds, a clubhouse, and surrounding wooded areas.

A building with a covered entrance, stone pillars, and a clear sky.

A hotel room with a large bed, two bedside tables with lamps, a small desk, and a red armchair.

A golf course with a clubhouse, a flag, and a parking area with cars.

14. Woodlake Lodge Golf and Country Club

Tazewell

James

4.160.000 ₫

4.669.600 ₫ total

includes taxes & fees

1 Oct - 2 Oct

A covered outdoor deck with wooden flooring and metal chairs.

A living room with two leather sofas, a wooden coffee table, a fireplace, and a TV on a stand.

A living room with two grey leather sofas, wooden flooring, a wooden coffee table, and a blue wall.

A bedroom with a bed, a dresser, a ceiling fan, and a large window.

15. Peaceful & Private! Pet-friendly Williamsburg Home

Williamsburg

3.276.000 ₫

7.994.220 ₫ total

includes taxes & fees

25 Sept - 26 Sept

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

A wooden cabin with a covered porch, furnished with wicker chairs and a glass table.

A rustic cabin interior with exposed wooden beams, a fireplace, a sofa, a wooden table, and a mounted deer head.

A rustic kitchen with wooden beams, a dining table with chairs, a blue door, and a staircase leading to another level.

16. Peaceful Mountain Cabin w/ Views in Williamsburg

Williamsburg

Chandler

3.276.000 ₫

8.870.680 ₫ total

includes taxes & fees

25 Sept - 26 Sept

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Stay near popular Middlesboro attractions

Middlesboro Mall

7.6/10 (62 reviews)

This regional shopping centre serves as a retail hub for Middlesboro with a mix of national and local stores. Browse fashion, home goods, and dining options in a straightforward, welcoming indoor environment.

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Middlesboro Country Club

Established in 1889, Middlesboro Country Club is America's oldest continuously played nine-hole golf course. Challenge yourself on undulating greens while surrounded by breathtaking Appalachian Mountain vistas.

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Bell County Historical Society Museum

8.2/10 (13 reviews)

Housed in the historic 1915 Dr. J.D. Cawood House, the Bell County Museum preserves Kentucky's regional heritage. Explore artefacts and photographs telling local cultural stories within this National Register landmark.

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Learn more about Middlesboro

Nestled in the Appalachian Mountains, Middlesboro invites you to explore the historic Cumberland Gap National Historical Park. Tee off at the scenic Middlesboro Country Club or delve into local heritage at the Bell County Historical Society Museum.

See all hotels in Middlesboro

Top Middlesboro Hotel Reviews

Pine Mountain State Resort Park

10/10 Excellent

"Delicious food too"

Quality Inn

10/10 Excellent

"Very helpful staff and clean, well kept rooms."

Suburban Studios Middlesboro

8/10 Good

"Bed was a little hard, but not too bad."

Quality Inn Harlan

10/10 Excellent

"Rooms nice and clean staff was wonderful as always. Enjoyed our stay. Will come back again"

More cheap stays in Middlesboro

Days Inn by Wyndham Jellico - Tennessee State Line

1417 5th Street Jellico TN

1.534.000 ₫

1.752.595 ₫ total

27 Sept - 28 Sept

includes taxes & fees

Quality Inn Harlan

2608 South Highway 421 Harlan KY

2.267.200 ₫

2.571.458 ₫ total

18 Oct - 19 Oct

includes taxes & fees

8.6/10 Excellent! (382 reviews)

Sleep Inn & Suites Middlesboro

1260 N, 12th Street Middlesboro KY

2.850.900 ₫

3.197.952 ₫ total

18 Oct - 19 Oct

includes taxes & fees

Holiday Inn Express Williamsburg by IHG

56 West Highway 92 Williamsburg KY

3.068.000 ₫

3.414.684 ₫ total

20 Oct - 21 Oct

includes taxes & fees

Holiday Inn Express Middlesboro by IHG

1252 N 12th St Middlesboro KY

3.614.000 ₫

3.983.980 ₫ total

27 Sept - 28 Sept

includes taxes & fees

Cumberland Gap Inn

630 Brooklyn Street Cumberland Gap TN

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Hotels in Middlesboro with star rating

Frequently asked questions

What's the seasonal weather in Middlesboro?

The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 5°C. Average annual precipitation for Middlesboro is 1581 mm.

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Find hotels in Middlesboro, KY from 1.752.595 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Middlesboro

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Middlesboro hotels

1. Econo Lodge Middlesboro

2. Sleep Inn & Suites Middlesboro

3. Boone Trail Inn

4. Suburban Studios Middlesboro

5. Holiday Inn Express Middlesboro by IHG

6. Imperial Inn Tazewell

7. Days Inn by Wyndham Jellico - Tennessee State Line

8. Holiday Inn Express Williamsburg by IHG

9. Dixie Plaza hotel

10. Quality Inn

11. Pine Mountain State Resort Park

12. Quality Inn Harlan

13. Tazewell Motor Lodge

14. Woodlake Lodge Golf and Country Club

15. Peaceful & Private! Pet-friendly Williamsburg Home

16. Peaceful Mountain Cabin w/ Views in Williamsburg

Stay near popular Middlesboro attractions

Middlesboro Mall

Middlesboro Country Club

Bell County Historical Society Museum

Learn more about Middlesboro

Top Middlesboro Hotel Reviews

Pine Mountain State Resort Park

Quality Inn

Suburban Studios Middlesboro

Quality Inn Harlan

More cheap stays in Middlesboro

Days Inn by Wyndham Jellico - Tennessee State Line

Quality Inn Harlan

Sleep Inn & Suites Middlesboro

Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Middlesboro by IHG

Cumberland Gap Inn

Hotels in Middlesboro with star rating

Frequently asked questions

Explore a world of travel with Expedia

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