Middlesboro Holiday Rentals

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Middlesboro holiday rentals

Exterior detail

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$1,345
HK$2,753 total
includes taxes & fees
19 May - 20 May
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Dining

Private bungalow close to LMU, ARH, Cumberland Gap

Private bungalow close to LMU, ARH, Cumberland Gap
Middlesboro
The price is HK$922
HK$2,211 total
includes taxes & fees
19 May - 20 May
Private bungalow close to LMU, ARH, Cumberland Gap
Interior

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

Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
Middlesboro
8.0 out of 10, Very good, (2 reviews)
"Clean"
United States
Phineas S.
The price is HK$1,387
HK$2,910 total
includes taxes & fees
28 May - 29 May
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
Exterior

Welcoming 3-bedroom house with AC in charming Middlesboro

Welcoming 3-bedroom house with AC in charming Middlesboro
Middlesboro
7.0 out of 10, Good, (2 reviews)
"Great area to stay in "
United States
Corinna E.
The price is HK$1,306
HK$2,699 total
includes taxes & fees
19 May - 20 May
Welcoming 3-bedroom house with AC in charming Middlesboro
Fridge, microwave, oven, stovetop

Outback Behind the Barn

Outback Behind the Barn
Ewing
The price is HK$799
HK$1,070 total
includes taxes & fees
19 May - 20 May
Outback Behind the Barn
Miscellaneous

The Nomad on Norris Lake

The Nomad on Norris Lake
New Tazewell
The price is HK$1,762
HK$2,958 total
includes taxes & fees
26 May - 27 May
The Nomad on Norris Lake
Terrace/patio

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, (9 reviews)
"We had a great stay. Everything was perfect. Would recommend this place to anyone visiting the area. "
United States
Tim D.
The price is HK$893
HK$1,510 total
includes taxes & fees
28 May - 29 May
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
Interior

Calm Country Oasis - Creek, ATV Trls & Norris Lake

Calm Country Oasis - Creek, ATV Trls & Norris Lake
Speedwell
9.6 out of 10, Exceptional, (24 reviews)
"We had a wonderful weekend:)"
United States
Bobbi F.
The price is HK$861
HK$2,064 total
includes taxes & fees
19 May - 20 May
Calm Country Oasis - Creek, ATV Trls & Norris Lake
Exterior

Robertson Ridge Hideaway Cottage

Robertson Ridge Hideaway Cottage
Hinkle
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful place "
United States
Isaac L.
The price is HK$881
HK$1,144 total
includes taxes & fees
21 May - 22 May
Robertson Ridge Hideaway Cottage
Fridge, microwave, oven, stovetop

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, (16 reviews)
"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.
The price is HK$783
HK$1,517 total
includes taxes & fees
25 May - 26 May
Harrogate Hideaway - 5 Min to LMU & Nat`l Park
Exterior

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Cumberland Gap
9.2 out of 10, Wonderful, (46 reviews)
"Cozy place perfect for what we needed. "
United States
Emily N.
The price is HK$854
HK$1,759 total
includes taxes & fees
19 May - 20 May
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Exterior

Blissful Bungalow across from LMU campus

Blissful Bungalow across from LMU campus
Harrogate
9.6 out of 10, Exceptional, (35 reviews)
"Very convenient to everything we needed to do, very clean and neat"
United States
Brandi L.
The price is HK$854
HK$1,721 total
includes taxes & fees
20 May - 21 May
Blissful Bungalow across from LMU campus
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, (25 reviews)
"Great location with friendly neighbors!"
United States
Evan C.
The price is HK$1,057
HK$2,115 total
includes taxes & fees
20 May - 21 May
Harrogate Home Mountain View’s Dog Friendly
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$940
HK$2,011 total
includes taxes & fees
7 Jun - 8 Jun
Beautiful Loft in the Woods
Outdoor dining

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$1,480
HK$2,927 total
includes taxes & fees
19 May - 20 May
The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!
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, (5 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$1,191
HK$2,237 total
includes taxes & fees
19 May - 20 May
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Terrace/patio

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
9.4 out of 10, Exceptional, (20 reviews)
"Cute and cozy! Perfect place for us to use as a home base while in town visiting family. Lots of attention to the details, kitchen facilities are up to date and super clean. Already looking forward to booking again!"
United States
Lynette M.
The price is HK$705
HK$1,409 total
includes taxes & fees
20 May - 21 May
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
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$2,404 total
includes taxes & fees
19 May - 20 May
Peaceful & Private! Pet-friendly Williamsburg Home
1 bedroom, free WiFi, bed sheets

Quaint Studio APT Near ATV Trails & Norris Lake

Quaint Studio APT Near ATV Trails & Norris Lake
LaFollette
9.6 out of 10, Exceptional, (11 reviews)
"Check in was very easy amazing little place. Loved the mornings going out to the porch and hearing the birds chirping. Definitely coming back and staying again "
United States
Melisza
The price is HK$360
HK$1,007 total
includes taxes & fees
31 May - 1 Jun
Quaint Studio APT Near ATV Trails & Norris Lake
TV

MOUNTAIN TOP CABIN WITH PARTNERING MARINA ON NORRIS LAKE

MOUNTAIN TOP CABIN WITH PARTNERING MARINA ON NORRIS LAKE
Rock Harbor
9.8 out of 10, Exceptional, (26 reviews)
"Great location for family gathering near local relatives. Beautiful views and close to New Tazewell. "
United States
Pamela D.
The price is HK$1,522
HK$3,861 total
includes taxes & fees
19 May - 20 May
MOUNTAIN TOP CABIN WITH PARTNERING MARINA ON NORRIS LAKE
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

Sleep Inn & Suites Middlesboro

Sleep Inn & Suites Middlesboro

10/10 Excellent
"Great property clean nice and room was amazing and quite"
Crystal 1-night trip
Posted 2 hours ago
Sleep Inn & Suites Middlesboro

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
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  • 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?

Beautiful Norris Lake Front A-Frame with Private Dock in Speedwell, TN: This holiday home rental outside of Middlesboro is located on a lake, and has a balcony, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, 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.