mountain view

Middlesboro Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sep - 13 Sep
In four months
9 Oct - 11 Oct

Our top choices for Middlesboro vacation 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 AED 631
AED 1,271 total
includes taxes & fees
21 Jun - 22 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 AED 468
AED 1,086 total
includes taxes & fees
7 Jul - 8 Jul
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 AED 642
AED 1,308 total
includes taxes & fees
15 Jul - 16 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 AED 762
AED 1,514 total
includes taxes & fees
23 Jun - 24 Jun
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
Property grounds

The Nomad on Norris Lake

The Nomad on Norris Lake
New Tazewell
The price is AED 826
AED 1,395 total
includes taxes & fees
6 Jul - 7 Jul
The Nomad on Norris Lake
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 AED 413
AED 537 total
includes taxes & fees
25 Jun - 26 Jun
Robertson Ridge Hideaway Cottage
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 AED 386
AED 671 total
includes taxes & fees
22 Jun - 23 Jun
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
House (2 Bedrooms) | Front of property

Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home
3.0 star property
Williamsburg
The price is AED 360
AED 1,127 total
includes taxes & fees
24 Jun - 25 Jun
Peaceful & Private! Pet-friendly Williamsburg Home
TV, fireplace, books

Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg

Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg
Williamsburg
10.0 out of 10, Exceptional, (1 review)
"Had a wonderful stay at this cabin. It was very beautiful and the location was very peaceful and quiet but not too far from other things. Would definitely need a 4 wheel drive vehicle to get to the cabin. The host was very nice and had great communication. Definitely recommend this cabin for anyone looking to relax and enjoy nature."
United States
Nancy A.
Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg
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 AED 290
AED 653 total
includes taxes & fees
23 Jun - 24 Jun
Remodeled Western Country Getaway Near Lake & Trails
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 AED 224
AED 535 total
includes taxes & fees
8 Jul - 9 Jul
Quaint Studio APT Near ATV Trails & Norris Lake
Smart TV, fireplace

Beautiful Loft in the Woods

Beautiful Loft in the Woods
Harlan
10.0 out of 10, Exceptional, (4 reviews)
"Another perfect stay in Melody's loft ! We highly recommend anyone stay here when in the Harlan area. It is quiet, absolutely spotless,with possibly the most comfortable bed we have ever slept on. Very close to restaurants and stores yet with that wonderful quiet country feel with a few deer running around. Thoughtfully stocked with bathroom items in case you forget something and some snacks and coffee and tea. Thanks again for a great weekend!!"
United States
Charles T.
The price is AED 441
AED 935 total
includes taxes & fees
21 Jun - 22 Jun
Beautiful Loft in the Woods
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 AED 323
AED 1,128 total
includes taxes & fees
24 Jun - 25 Jun
Peaceful & Private! Pet-Friendly Williamsburg Home
Fridge, microwave, oven, stovetop

Updated Apt in Country - ATV Trls & Norris Lake

Updated Apt in Country - ATV Trls & Norris Lake
LaFollette
9.6 out of 10, Exceptional, (5 reviews)
"Fantastic stay! The place was clean, comfortable, and exactly as described. They were an excellent host—responsive and helpful. We felt right at home and would absolutely stay here again. Highly recommend!"
United States
madison a.
The price is AED 220
AED 573 total
includes taxes & fees
21 Jun - 22 Jun
Updated Apt in Country - ATV Trls & 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 AED 298
AED 623 total
includes taxes & fees
22 Jun - 23 Jun
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
Interior

The Highlands Cabin ~ Norris Lake Views & Modern Comfort

The Highlands Cabin ~ Norris Lake Views & Modern Comfort
New Tazewell
10.0 out of 10, Exceptional, (4 reviews)
"The cabin was clean, cozy, and overall amazing! "
United States
Fannie
The price is AED 479
AED 821 total
includes taxes & fees
22 Jun - 23 Jun
The Highlands Cabin ~ Norris Lake Views & Modern Comfort
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 AED 511
AED 972 total
includes taxes & fees
22 Jun - 23 Jun
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
House (1 Bedroom) | Interior

Peaceful Mountain Cabin w/ Views in Williamsburg

Peaceful Mountain Cabin w/ Views in Williamsburg
2.0 star property
Williamsburg
Peaceful Mountain Cabin w/ Views in Williamsburg
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 AED 573
AED 1,184 total
includes taxes & fees
24 Jun - 25 Jun
Calm Country Oasis - Creek, ATV Trls & 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 AED 404
AED 819 total
includes taxes & fees
21 Jun - 22 Jun
Blissful Bungalow across from LMU campus
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middlesboro Hotel Reviews

Days Inn by Wyndham Jellico - Tennessee State Line

Days Inn by Wyndham Jellico - Tennessee State Line

10/10 Excellent
"The TV was very hard to operate & when shown still had no easy way to use it. The Breakfast was decent but a little skimpy and need more variety. 1 kind of sweet, 2 kinds of cereal, etc. Breakfast location also not convenient. Night check-in person very helpful and friendly. excellent."
Phillip 1-night trip
Posted 17 hours ago
Days Inn by Wyndham Jellico - Tennessee State Line

Frequently asked questions

Are there vacation rentals in Middlesboro?

Yes, we offer vacation rentals close to the most popular sights in Middlesboro, or you can choose a secluded option if you'd like a relaxing place to 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's the top vacation rental that Middlesboro has to offer?

Beautiful Norris Lake WATERFRONT. Near Flat Hollow Marina. Private dock.: This vacation home near Middlesboro is located on a lake and has a balcony, a selection of games, and a barbecue grill 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 you can cook with friends or family.

How many vacation rentals are there in Middlesboro?

With 6 Expedia vacation rentals, you're sure 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 Country Club and Cumberland Gap National Historical Park are other places worth a visit.

What’s a vacation rental in Middlesboro like?

Vacation rentals are private properties you can stay in for short or long periods in Middlesboro. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for small groups.