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

Middlesboro Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Middlesboro holiday rentals

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

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

Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Middlesboro
9.2 out of 10, Wonderful, (7 reviews)
"We enjoyed our stay. "
United States
Emily S.
The price is HK$1,602
HK$3,096 total
includes taxes & fees
12 Oct - 13 Oct
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
A living room with a stone fireplace, wooden walls, a sofa, a coffee table, and a TV mounted on the wall.

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

Gorgeous 4-bedroom house in Middlesboro KY with WiFi, AC. Minutes from LMU
Middlesboro
10.0 out of 10, Exceptional, (19 reviews)
"Lots of room. Clean. Good host."
United States
Konnie D.
The price is HK$1,059
HK$2,802 total
includes taxes & fees
28 Oct - 29 Oct
Gorgeous 4-bedroom house in Middlesboro KY with WiFi, AC. Minutes from LMU
A living room with a TV on a wooden stand, a white chair, a small table, and a sofa.

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

House close to ARH Hospital, Tackett Creek & LMU!
Middlesboro
7.4 out of 10, Good, (3 reviews)
"Advertised would sleep 12, yes it had beds for 12, but I guess we were to share towels , could be cleaner, food and trash under sofa cushions. Had to hunt for the WiFi password."
United States
Elita W.
The price is HK$1,958
HK$3,661 total
includes taxes & fees
29 Oct - 30 Oct
House close to ARH Hospital, Tackett Creek & LMU!
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

Welcoming 3-bedroom house with AC in charming Middlesboro
Middlesboro
8.0 out of 10, Very good, (3 reviews)
"Great area to stay in "
United States
Corinna E.
The price is HK$1,579
HK$3,070 total
includes taxes & fees
11 Oct - 12 Oct
Welcoming 3-bedroom house with AC in charming Middlesboro
A dining area with a table set for four, a ceiling fan, and a sign above reading 'BE OUR GUEST'.

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

Private bungalow close to LMU, ARH, Cumberland Gap
Middlesboro
The price is HK$1,229
HK$2,612 total
includes taxes & fees
12 Oct - 13 Oct
Private bungalow close to LMU, ARH, Cumberland Gap
Private kitchen

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

Harrogate Hideaway - 5 Min to LMU & Nat`l Park
Harrogate
9.8 out of 10, Exceptional, (20 reviews)
"Absolutely perfect!Plenty of space, beds were great and so comfortable. Well equipped and the best part so quiet!!! Perfect location for parents visiting LMU students, I highly recommend!"
United States
Amy C.
The price is HK$777
HK$1,527 total
includes taxes & fees
20 Oct - 21 Oct
Harrogate Hideaway - 5 Min to LMU & Nat`l Park
An aerial view of a campus with multiple buildings, a central tower, and a large open grassy area.

7. Blissful Bungalow across from LMU campus

Blissful Bungalow across from LMU campus
Harrogate
9.6 out of 10, Exceptional, (42 reviews)
"Very convenient to everything we needed to do, very clean and neat"
United States
Brandi L.
The price is HK$855
HK$1,764 total
includes taxes & fees
21 Oct - 22 Oct
Blissful Bungalow across from LMU campus
A rustic wooden building with a porch, stone pillars, and potted plants.

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

Luxury Brooklyn St APT - Near LMU & Nat’l Park
Cumberland Gap
9.8 out of 10, Exceptional, (30 reviews)
"Great location So close to so much hiking."
United States
Theresa l.
The price is HK$879
HK$1,692 total
includes taxes & fees
4 Oct - 5 Oct
Luxury Brooklyn St APT - Near LMU & Nat’l Park
A wooden deck with a railing, a brick building, and a door with a window.

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

Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Pineville
10.0 out of 10, Exceptional, (12 reviews)
"Clean and quiet place to stay when visiting the area. Will definitely consider this place again when we visit Pineville again! "
United States
seth r.
The price is HK$1,250
HK$2,321 total
includes taxes & fees
2 Oct - 3 Oct
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
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 Home Mountain View’s Dog Friendly
Harrogate
10.0 out of 10, Exceptional, (29 reviews)
"Great place to stay. "
United States
Jodi D.
The price is HK$1,059
HK$2,127 total
includes taxes & fees
4 Oct - 5 Oct
Harrogate Home Mountain View’s Dog Friendly
An outdoor patio with a wooden table and wicker chairs.

11. The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!

The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!
Pineville
9.4 out of 10, Exceptional, (6 reviews)
"Such a cute little place we have stayed twice already"
United States
Cassie S.
The price is HK$1,483
HK$2,941 total
includes taxes & fees
11 Oct - 12 Oct
The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!
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

Calm Country Oasis - Creek, ATV Trls & Norris Lake
Speedwell
9.6 out of 10, Exceptional, (26 reviews)
"Clean home, responsive host, beautiful location, family friendly."
United States
Anna S.
The price is HK$855
HK$2,060 total
includes taxes & fees
3 Oct - 4 Oct
Calm Country Oasis - Creek, ATV Trls & Norris Lake
A dining area with a wooden table set for four, a lamp, and framed artwork on the walls.

13. 2-bedroom loft apartment in adorable Pineville close to Pine Mountain State Park

2-bedroom loft apartment in adorable Pineville close to Pine Mountain State Park
Pineville
10.0 out of 10, Exceptional, (1 review)
"We stayed for the 95th Mountain Laurel Festival and LOVED the location, access to all festival activities, and how easy it was to communicate with the renter. We hope to make this a tradition and will stay here again!"
United States
jennifer w.
The price is HK$1,017
HK$2,340 total
includes taxes & fees
4 Oct - 5 Oct
2-bedroom loft apartment in adorable Pineville close to Pine Mountain State Park
A covered outdoor deck with wooden flooring and metal chairs.

14. Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home
3.0 star property
Williamsburg
The price is HK$989
HK$2,412 total
includes taxes & fees
13 Oct - 14 Oct
Peaceful & Private! Pet-friendly Williamsburg Home
An outdoor patio with a fire pit, surrounded by chairs and a pergola with string lights.

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

Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
Speedwell
9.2 out of 10, Wonderful, (28 reviews)
"The property was ideal. It was affordable, not too remote and had everything we needed."
United States
Julie R.
The price is HK$671
HK$1,372 total
includes taxes & fees
14 Oct - 15 Oct
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
A wooden interior with a kitchen, bar area, and a ceiling-mounted projector.

16. The Lodge Cabin ~Norris Lake Views and Mountain Backdrops

The Lodge Cabin ~Norris Lake Views and Mountain Backdrops
New Tazewell
10.0 out of 10, Exceptional, (7 reviews)
"It was a lovely little home! Very clean and perfect for my family!"
United States
Lauren W.
The price is HK$1,024
HK$1,770 total
includes taxes & fees
4 Oct - 5 Oct
The Lodge Cabin ~Norris Lake Views and Mountain Backdrops
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.

17. One Bedroom Rustic Cabin

One Bedroom Rustic Cabin
Speedwell
The price is HK$384
HK$765 total
includes taxes & fees
13 Oct - 14 Oct
One Bedroom Rustic Cabin
A wooden deck with a rocking chair and a wicker sofa.

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

Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
Tazewell
9.2 out of 10, Wonderful, (12 reviews)
"Very nice cabin, comfortable and homey."
United States
Carla C.
The price is HK$745
HK$1,346 total
includes taxes & fees
6 Oct - 7 Oct
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
A cozy cabin interior with a kitchen area, two bar stools, a refrigerator, a sink, and a small stove.

19. The Highlands Cabin ~ Norris Lake Views & Modern Comfort

The Highlands Cabin ~ Norris Lake Views & Modern Comfort
New Tazewell
10.0 out of 10, Exceptional, (9 reviews)
"The cabin was clean, cozy, and overall amazing! "
United States
Fannie
The price is HK$1,024
HK$1,770 total
includes taxes & fees
4 Oct - 5 Oct
The Highlands Cabin ~ Norris Lake Views & Modern Comfort
A modern kitchen with white cabinets, a stainless steel refrigerator, a wooden island with chairs, and a window providing natural light.

20. Norris Lake Cabin Getaway, Sleeps 6・View・Fire pit

Norris Lake Cabin Getaway, Sleeps 6・View・Fire pit
New Tazewell
8.0 out of 10, Very good, (1 review)
"It is a lovely dated home. We felt comfortable in our stay. It is situated between two curves so pulling in and out with a truck and trailer is a bit difficult as cars fly on that road. Other then that it had everything we needed for our short visit to town"
United States
Lauren W.
The price is HK$847
HK$4,158 total
includes taxes & fees
15 Oct - 16 Oct
Norris Lake Cabin Getaway, Sleeps 6・View・Fire pit
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.
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Top Middlesboro Hotel Reviews

Pine Mountain State Resort Park

Pine Mountain State Resort Park

10/10 Excellent
"Very nice!"
Hal and Sherry 2-night trip
Posted 1 day ago
Pine Mountain State Resort Park

Find out more about Middlesboro

Search for holiday rentals in Middlesboro on Expedia! You can easily find your home rentals, villas, holiday apartments in Middlesboro using one of the methods below:

  • View our selection of featured holiday rentals in Middlesboro
  • Use the map to find apartments and other holiday homes in the Middlesboro neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middlesboro while they last

Look no further and take a look at our great range of rental properties in Middlesboro!

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.