Middlesboro Holiday Rentals

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Middlesboro holiday rentals

Desk, iron/ironing board, WiFi, bed sheets

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$2,754 total
includes taxes & fees
27 May - 28 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$2,212 total
includes taxes & fees
27 May - 28 May
Private bungalow close to LMU, ARH, Cumberland Gap
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$1,307
HK$2,700 total
includes taxes & fees
27 May - 28 May
Welcoming 3-bedroom house with AC in charming Middlesboro
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$1,388
HK$2,911 total
includes taxes & fees
28 May - 29 May
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
Miscellaneous

RV/Camper Sites. No Electric

RV/Camper Sites. No Electric
Speedwell
The price is HK$329
HK$614 total
includes taxes & fees
27 May - 28 May
RV/Camper Sites. No Electric
Private kitchen

The Nomad on Norris Lake

The Nomad on Norris Lake
New Tazewell
The price is HK$1,763
HK$2,967 total
includes taxes & fees
1 Jun - 2 Jun
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$885
HK$1,502 total
includes taxes & fees
2 Jun - 3 Jun
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
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$776
HK$1,647 total
includes taxes & fees
27 May - 28 May
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Property grounds

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
28 May - 29 May
Robertson Ridge Hideaway Cottage
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$995
HK$2,239 total
includes taxes & fees
30 May - 31 May
Calm Country Oasis - Creek, ATV Trls & Norris Lake
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$776
HK$1,509 total
includes taxes & fees
27 May - 28 May
Harrogate Hideaway - 5 Min to LMU & Nat`l Park
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$353
HK$998 total
includes taxes & fees
27 May - 28 May
Quaint Studio APT Near ATV Trails & Norris Lake
Exterior

Blissful Bungalow across from LMU campus

Blissful Bungalow across from LMU campus
Harrogate
9.6 out of 10, Exceptional, (36 reviews)
"Very convenient to everything we needed to do, very clean and neat"
United States
Brandi L.
The price is HK$854
HK$1,722 total
includes taxes & fees
27 May - 28 May
Blissful Bungalow across from LMU campus
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)
"Was in a great location to be able to go to multiple riding locations. "
United States
Sara R.
The price is HK$705
HK$1,410 total
includes taxes & fees
2 Jun - 3 Jun
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
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$1,995 total
includes taxes & fees
8 Jun - 9 Jun
Beautiful Loft in the Woods
Front of property

Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home
3.0 star property
Williamsburg
The price is HK$768
HK$2,405 total
includes taxes & fees
3 Jun - 4 Jun
Peaceful & Private! Pet-friendly Williamsburg Home
Interior

The Highlands Cabin Retreat at Norris Lake

The Highlands Cabin Retreat at Norris Lake
New Tazewell
10.0 out of 10, Exceptional, (4 reviews)
"The cabin was clean, cozy, and overall amazing! "
United States
Fannie
The price is HK$1,023
HK$1,744 total
includes taxes & fees
27 May - 28 May
The Highlands Cabin Retreat at 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, (25 reviews)
"Great location with friendly neighbors!"
United States
Evan C.
The price is HK$1,072
HK$2,141 total
includes taxes & fees
1 Jun - 2 Jun
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, (6 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$1,192
HK$2,238 total
includes taxes & fees
3 Jun - 4 Jun
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
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
9.6 out of 10, Exceptional, (5 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$1,481
HK$2,929 total
includes taxes & fees
27 May - 28 May
The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!
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

Days Inn by Wyndham Jellico - Tennessee State Line

Days Inn by Wyndham Jellico - Tennessee State Line

8/10 Good
"Continental breakfast was disappointing; only weak coffee and waffles, juice. Breakfast lounge was decorated nicely and safe. Pool unusable; same with other amenities. NO wifi and internet! What is with that."
diane 1-night trip
Posted less than an hour ago
Days Inn by Wyndham Jellico - Tennessee State Line

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?

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.