Middlesboro Holiday Rentals

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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

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,

4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
Middlesboro
10.0 out of 10, Exceptional, (25 reviews)
"Very nice and extra clean great time"
United States
Johnny C.
The price is HK$931
HK$1,802 total
includes taxes & fees
1 Mar - 2 Mar
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
Exterior detail

Welcoming 3-bedroom house with AC in charming Middlesboro

Welcoming 3-bedroom house with AC in charming Middlesboro
Middlesboro
The price is HK$1,049
HK$2,304 total
includes taxes & fees
2 Mar - 3 Mar
Welcoming 3-bedroom house with AC in charming Middlesboro
3 bedrooms, desk, iron/ironing board, travel cot

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, (5 reviews)
"We enjoyed our stay. "
United States
Emily S.
The price is HK$1,369
HK$2,898 total
includes taxes & fees
9 Mar - 10 Mar
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Exterior

3-bedroom bungalow in the heart of Crater City, near airport LMU & hiking trails

3-bedroom bungalow in the heart of Crater City, near airport LMU & hiking trails
Middlesboro
The price is HK$995
HK$2,244 total
includes taxes & fees
2 Mar - 3 Mar
3-bedroom bungalow in the heart of Crater City, near airport LMU & hiking trails
Microwave, oven, stovetop

Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU

Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
Middlesboro
10.0 out of 10, Exceptional, (1 review)
"Clean"
United States
Phineas S.
The price is HK$1,393
HK$2,717 total
includes taxes & fees
17 Mar - 18 Mar
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
Fridge, microwave, oven, stovetop

Outback Behind the Barn

Outback Behind the Barn
Ewing
The price is HK$798
HK$1,069 total
includes taxes & fees
1 Mar - 2 Mar
Outback Behind the Barn
Front of property

Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home
3.0 star property
Williamsburg
The price is HK$767
HK$2,401 total
includes taxes & fees
1 Mar - 2 Mar
Peaceful & Private! Pet-friendly Williamsburg Home
Property grounds

Lakefront, minimal steps to water. Large private dock, Chef's kitchen

Lakefront, minimal steps to water. Large private dock, Chef's kitchen
Speedwell
10.0 out of 10, Exceptional, (16 reviews)
"Lovely home, great location in a quiet cove. Definitely intend to come back."
United States
Jeri M.
The price is HK$2,735
HK$8,541 total
includes taxes & fees
1 Mar - 2 Mar
Lakefront, minimal steps to water. Large private dock, Chef's kitchen
Terrace/patio

Lakefront Cabin, Sleeps 16・Dock・Fire Pit・Hot Tub

Lakefront Cabin, Sleeps 16・Dock・Fire Pit・Hot Tub
New Tazewell
The price is HK$2,793
HK$6,418 total
includes taxes & fees
1 Mar - 2 Mar
Lakefront Cabin, Sleeps 16・Dock・Fire Pit・Hot Tub
TV, fireplace, DVD player, offices

3 Story Lake Escape, Sleeps 16・Hot Tub・Pool Table

3 Story Lake Escape, Sleeps 16・Hot Tub・Pool Table
New Tazewell
The price is HK$2,011
HK$7,515 total
includes taxes & fees
1 Mar - 2 Mar
3 Story Lake Escape, Sleeps 16・Hot Tub・Pool Table
Interior

Calm Country Oasis - Creek, ATV Trls & Norris Lake

Calm Country Oasis - Creek, ATV Trls & Norris Lake
Speedwell
9.4 out of 10, Exceptional, (22 reviews)
"We had a wonderful weekend:)"
United States
Bobbi F.
The price is HK$861
HK$1,992 total
includes taxes & fees
5 Mar - 6 Mar
Calm Country Oasis - Creek, ATV Trls & Norris Lake
Fridge, microwave, oven, stovetop

Harrogate Home Mountain View’s Dog Friendly

Harrogate Home Mountain View’s Dog Friendly
Harrogate
10.0 out of 10, Exceptional, (23 reviews)
"Great location with friendly neighbors!"
United States
Evan C.
The price is HK$1,144
HK$2,239 total
includes taxes & fees
1 Mar - 2 Mar
Harrogate Home Mountain View’s Dog Friendly
Property grounds

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, (2 reviews)
"We stayed here for a wedding weekend in Pineville, KY, and it was absolutely perfect from start to finish. The home was spotless, cozy, and had everything we could possibly need. The beds were so comfortable, and we instantly felt at home the moment we walked in.What truly set this stay apart was the host’s kindness and above-and-beyond hospitality. We got lost in the middle of the night trying to find the property, and the host stayed on the phone with us, patiently guiding us right to the...
United States
Samantha P.
The price is HK$1,246
HK$2,314 total
includes taxes & fees
3 Mar - 4 Mar
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Interior

The Highlands Cabin Retreat at Norris Lake

The Highlands Cabin Retreat at Norris Lake
New Tazewell
10.0 out of 10, Exceptional, (2 reviews)
"The cabin was clean, cozy, and overall amazing! "
United States
Fannie
The price is HK$1,021
HK$1,757 total
includes taxes & fees
1 Mar - 2 Mar
The Highlands Cabin Retreat at Norris Lake
Terrace/patio

Lake Front ★ No Wake w/ Dock ★ Gameroom ★ Carved FirePit ★ 2nd House Available

Lake Front ★ No Wake w/ Dock ★ Gameroom ★ Carved FirePit ★ 2nd House Available
LaFollette
10.0 out of 10, Exceptional, (46 reviews)
"House was spectacular, beds were very comfortable, plenty to do in the area and the lake was just beautiful. Would definitely stay here again!"
United States
Brooke R.
The price is HK$1,792
HK$5,571 total
includes taxes & fees
1 Mar - 2 Mar
Lake Front ★ No Wake w/ Dock ★ Gameroom ★ Carved FirePit ★ 2nd House Available
Smart TV, fireplace

Beautiful Loft in the Woods

Beautiful Loft in the Woods
Harlan
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful setting. Incredible space well laid out. Owner was very engaging. "
United States
Fred
The price is HK$939
HK$2,027 total
includes taxes & fees
2 Mar - 3 Mar
Beautiful Loft in the Woods
Interior

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, (3 reviews)
"The home was just perfect for what we needed. Looking forward to seeing how it comes out when all construction is finished! Host was very responsive. Will stay again"
United States
Kami L.
The price is HK$1,401
HK$2,743 total
includes taxes & fees
1 Mar - 2 Mar
The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!
TV

Floating house on the beautiful Norris Lake!

Floating house on the beautiful Norris Lake!
New Tazewell
The price is HK$1,408
HK$2,422 total
includes taxes & fees
1 Mar - 2 Mar
Floating house on the beautiful Norris Lake!
Property grounds

Stunning Lakeview Home・Game Room・Dock・Hot Tub

Stunning Lakeview Home・Game Room・Dock・Hot Tub
Lakeside Estates
The price is HK$3,575
HK$9,846 total
includes taxes & fees
1 Mar - 2 Mar
Stunning Lakeview Home・Game Room・Dock・Hot Tub
Exterior

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Cumberland Gap
9.4 out of 10, Exceptional, (44 reviews)
"Great location. Easy walk to town and close to hiking areas. Highly recommend. "
United States
Linda O.
The price is HK$775
HK$1,645 total
includes taxes & fees
15 Mar - 16 Mar
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
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

Boone Trail Inn

Boone Trail Inn

10/10 Excellent
"The room was clean. Very quiet for the price, although I don’t think the pop machine was working "
Jack 1-night trip
Posted 5 days ago
Boone Trail Inn

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:

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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?

9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock: This holiday home rental outside of Middlesboro is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease 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. You can relax into your holiday with a selection of games and 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.