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Middlesboro Holiday Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

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$1,346
HK$2,755 total
includes taxes & fees
23 Jun - 24 Jun
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$1,016
HK$2,338 total
includes taxes & fees
29 Jun - 30 Jun
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
8.0 out of 10, Very good, (3 reviews)
"Great area to stay in "
United States
Corinna E.
The price is HK$1,352
HK$2,771 total
includes taxes & fees
23 Jul - 24 Jul
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
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$1,617
HK$3,220 total
includes taxes & fees
23 Jul - 24 Jul
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
WiFi, bed sheets

Modern 20’ Travel Trailer with bunks and a queen bed

Modern 20’ Travel Trailer with bunks and a queen bed
Speedwell
The price is HK$721
HK$1,221 total
includes taxes & fees
23 Jun - 24 Jun
Modern 20’ Travel Trailer with bunks and a queen bed
Property grounds

The Nomad on Norris Lake

The Nomad on Norris Lake
New Tazewell
The price is HK$1,763
HK$2,976 total
includes taxes & fees
6 Jul - 7 Jul
The Nomad on Norris Lake
Interior

One Bedroom Rustic Cabin

One Bedroom Rustic Cabin
Speedwell
The price is HK$384
HK$764 total
includes taxes & fees
23 Jun - 24 Jun
One Bedroom Rustic Cabin
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$2,406 total
includes taxes & fees
24 Jun - 25 Jun
Peaceful & Private! Pet-friendly Williamsburg Home
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$882
HK$1,145 total
includes taxes & fees
25 Jun - 26 Jun
Robertson Ridge Hideaway Cottage
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$1,089
HK$2,034 total
includes taxes & fees
25 Jun - 26 Jun
Blissful Bungalow across from LMU campus
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$470
HK$1,133 total
includes taxes & fees
8 Jul - 9 Jul
Quaint Studio APT Near ATV Trails & Norris Lake
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, (22 reviews)
"Was in a great location to be able to go to multiple riding locations. "
United States
Sara R.
The price is HK$635
HK$1,330 total
includes taxes & fees
24 Jun - 25 Jun
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
Hair dryer, towels, soap, toilet paper

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, (11 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$815
HK$1,424 total
includes taxes & fees
23 Jun - 24 Jun
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
Fridge, microwave, oven, stovetop

Remodeled Western Country Getaway Near Lake & Trails

Remodeled Western Country Getaway Near Lake & Trails
LaFollette
10.0 out of 10, Exceptional, (1 review)
"Very clean and nice apartment. Just as advertised. Had everything we needed and we were very pleased. Great place! You will not be disappointed. We will definitely be going back!"
United States
Gregory T.
The price is HK$619
HK$1,392 total
includes taxes & fees
6 Jul - 7 Jul
Remodeled Western Country Getaway Near Lake & Trails
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)
"Property is great for access to trails for SxS and the property it beautiful. You can have a bomb fire or enjoy the water. We loved it."
United States
Colt L.
The price is HK$1,199
HK$2,491 total
includes taxes & fees
24 Jun - 25 Jun
Calm Country Oasis - Creek, ATV Trls & Norris Lake
Terrace/patio

Peaceful & Private! Pet-Friendly Williamsburg Home

Peaceful & Private! Pet-Friendly Williamsburg Home
Williamsburg
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful peaceful setting, great views! Host was very nice and helpful! Home was very clean and comfortable. Pet friendly, and kid friendly :)Highly recommend!"
United States
Alicia M.
The price is HK$690
HK$2,408 total
includes taxes & fees
24 Jun - 25 Jun
Peaceful & Private! Pet-Friendly Williamsburg Home
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$1,066
HK$2,023 total
includes taxes & fees
28 Jun - 29 Jun
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
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)
"Such a cute little apartment! It had everything we needed for our stay. "
United States
Cindy
The price is HK$1,105
HK$1,916 total
includes taxes & fees
5 Jul - 6 Jul
Harrogate Hideaway - 5 Min to LMU & Nat`l Park
Interior

Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's

Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's
Sharps Chapel
10.0 out of 10, Exceptional, (6 reviews)
"This was definitely the most romantic VRBO we’ve stayed at!!! Very clean, and the view from all of the balconies was incredible!!! "
United States
Stan N.
The price is HK$1,107
HK$2,404 total
includes taxes & fees
24 Jun - 25 Jun
Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's
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$2,895 total
includes taxes & fees
25 Jun - 26 Jun
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

Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG

10/10 Excellent
"Very professional"
Jerry 1-night trip
Posted 2 hours 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
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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?

Lake Front 2-Bedroom Home W/ Privacy! Beautiful Views & Numerous Amenities...: This holiday home rental outside of Middlesboro is located on a lake, and has a patio, a private garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

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 Country Club 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.