Photo by Ashlee Adams

Middlesboro Holiday Rentals

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Check prices for these dates

Tonight
7 Jan - 8 Jan
Tomorrow
8 Jan - 9 Jan
This weekend
9 Jan - 11 Jan
Next weekend
16 Jan - 18 Jan

Our top choices for Middlesboro holiday rentals

2 bedrooms, iron/ironing board, free WiFi, bed sheets
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,

Holiday Home in Middlesboro

4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
10.0 out of 10, Exceptional, (23)
"Very nice and extra clean great time"
United States
Johnny C.
The price is HK$927
HK$1,803 total
includes taxes & fees
10 Jan - 11 Jan
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
Exterior
3-bedroom home away from home in Middesboro. A family friendly environment.

Holiday Home in Middlesboro

3-bedroom home away from home in Middesboro. A family friendly environment.
2.0 star property
The price is HK$797
HK$1,265 total
includes taxes & fees
1 Feb - 2 Feb
3-bedroom home away from home in Middesboro. A family friendly environment.
3 bedrooms, desk, iron/ironing board, travel cot
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

Holiday Home in Middlesboro

Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
9.2 out of 10, Wonderful, (5)
"We enjoyed our stay. "
United States
Emily S.
The price is HK$1,363
HK$2,885 total
includes taxes & fees
11 Jan - 12 Jan
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Exterior detail
Welcoming 3-bedroom house with AC in charming Middlesboro

Holiday Home in Middlesboro

Welcoming 3-bedroom house with AC in charming Middlesboro
The price is HK$1,246
HK$2,335 total
includes taxes & fees
26 Jan - 27 Jan
Welcoming 3-bedroom house with AC in charming Middlesboro
Microwave, oven, stovetop
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU

Holiday Home in Middlesboro

Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
10.0 out of 10, Exceptional, (1)
"Clean"
United States
Phineas S.
The price is HK$1,227
HK$2,520 total
includes taxes & fees
21 Jan - 22 Jan
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
WiFi, bed sheets
Modern 20’ Travel Trailer with bunks and a queen bed

Mobile Home in Speedwell

Modern 20’ Travel Trailer with bunks and a queen bed
2.0 star property
The price is HK$514
HK$986 total
includes taxes & fees
8 Jan - 9 Jan
Modern 20’ Travel Trailer with bunks and a queen bed
Miscellaneous
RV/Camper Sites. No Electric

Camping in Speedwell

RV/Camper Sites. No Electric
2.0 star property
The price is HK$274
HK$551 total
includes taxes & fees
8 Jan - 9 Jan
RV/Camper Sites. No Electric
Fridge, microwave, oven, stovetop
Outback Behind the Barn

Mobile Home in Ewing

Outback Behind the Barn
The price is HK$794
HK$1,064 total
includes taxes & fees
8 Jan - 9 Jan
Outback Behind the Barn
Terrace/patio
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!

Cabin in Tazewell

Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
10.0 out of 10, Exceptional, (5)
The price is HK$666
HK$1,253 total
includes taxes & fees
10 Jan - 11 Jan
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
Fridge, microwave, oven, stovetop
Harrogate Hideaway - 5 Min to LMU & Nat`l Park

Apartment in Harrogate

Harrogate Hideaway - 5 Min to LMU & Nat`l Park
9.8 out of 10, Exceptional, (8)
"Harrogate Hideaway was a very clean and cute place to stay. We really enjoyed our time here. Our host Ciara was great!"
United States
Carla P.
Harrogate Hideaway - 5 Min to LMU & Nat`l Park
Exterior
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cottage in Cumberland Gap

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
9.2 out of 10, Wonderful, (42)
"Great location. Easy walk to town and close to hiking areas. Highly recommend. "
United States
Linda O.
The price is HK$771
HK$1,645 total
includes taxes & fees
8 Jan - 9 Jan
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Front of property
Peaceful & Private! Pet-friendly Williamsburg Home

Cottage in Williamsburg

Peaceful & Private! Pet-friendly Williamsburg Home
3.0 star property
The price is HK$763
HK$2,390 total
includes taxes & fees
9 Jan - 10 Jan
Peaceful & Private! Pet-friendly Williamsburg Home
Interior
One Bedroom Rustic Cabin

Cabin in Speedwell

One Bedroom Rustic Cabin
2.0 star property
The price is HK$305
HK$673 total
includes taxes & fees
7 Feb - 8 Feb
One Bedroom Rustic Cabin
Smart TV, fireplace
Beautiful Loft in the Woods

Apartment in Harlan

Beautiful Loft in the Woods
10.0 out of 10, Exceptional, (3)
"Beautiful setting. Incredible space well laid out. Owner was very engaging. "
United States
Fred
The price is HK$856
HK$1,811 total
includes taxes & fees
18 Jan - 19 Jan
Beautiful Loft in the Woods
Terrace/patio
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina

Holiday Home in Speedwell

Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
9.4 out of 10, Exceptional, (19)
"It was exceptional "
United States
Dennis W.
The price is HK$561
HK$1,241 total
includes taxes & fees
13 Jan - 14 Jan
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
Exterior
Luxury Brooklyn St APT - Near LMU & Nat’l Park

Apartment in Cumberland Gap

Luxury Brooklyn St APT - Near LMU & Nat’l Park
9.6 out of 10, Exceptional, (25)
"This place was just as described and perfect for our stay!"
United States
Melissa M.
The price is HK$771
HK$1,557 total
includes taxes & fees
8 Jan - 9 Jan
Luxury Brooklyn St APT - Near LMU & Nat’l Park
Fridge, microwave, oven, stovetop
Harrogate Home Mountain View’s Dog Friendly

Holiday Home in Harrogate

Harrogate Home Mountain View’s Dog Friendly
10.0 out of 10, Exceptional, (22)
"Great location with friendly neighbors!"
United States
Evan C.
The price is HK$1,227
HK$2,338 total
includes taxes & fees
19 Jan - 20 Jan
Harrogate Home Mountain View’s Dog Friendly
Property grounds
Robertson Ridge Hideaway Cottage

Cottage in Hinkle

Robertson Ridge Hideaway Cottage
2.0 star property
The price is HK$876
HK$1,138 total
includes taxes & fees
8 Jan - 9 Jan
Robertson Ridge Hideaway Cottage
Interior
The Highlands Cabin Retreat at Norris Lake

Cabin in New Tazewell

The Highlands Cabin Retreat at Norris Lake
2.0 star property
10.0 out of 10, Exceptional, (2)
"The cabin was clean, cozy, and overall amazing! "
United States
Fannie
The price is HK$903
HK$1,622 total
includes taxes & fees
8 Jan - 9 Jan
The Highlands Cabin Retreat at Norris Lake
Terrace/patio
Peaceful & Private! Pet-Friendly Williamsburg Home

Holiday Home in Williamsburg

Peaceful & Private! Pet-Friendly Williamsburg Home
2.0 star property
The price is HK$685
HK$2,401 total
includes taxes & fees
8 Jan - 9 Jan
Peaceful & Private! Pet-Friendly Williamsburg Home
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

Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG

10/10 Excellent
"Courteous staff and clean room "
alexandria 1-night trip
Posted 5 days ago
Holiday Inn Express Williamsburg by IHG

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?

8BR Lakefront Lux Retreat: Private Dock, Sleeps 28: This holiday home rental outside of Middlesboro is located on a lake, and has a fireplace, an arcade/games room and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

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, Cumberland Gap National Historical Park and Middlesboro Mall 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.