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Middlesboro Vacation Rentals

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Our top choices for Middlesboro vacation rentals

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.
$305 nightly
The price is $352
Jun 28 - Jun 29
Total with taxes and fees
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

Private bungalow close to LMU, ARH, Cumberland Gap

Private bungalow close to LMU, ARH, Cumberland Gap
Middlesboro
$256 nightly
The price is $296
Jul 7 - Jul 8
Total with taxes and fees
Private bungalow close to LMU, ARH, Cumberland Gap

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.
$302 nightly
The price is $348
Jul 23 - Jul 24
Total with taxes and fees
Welcoming 3-bedroom house with AC in charming Middlesboro

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.
$351 nightly
The price is $405
Jul 23 - Jul 24
Total with taxes and fees
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU

Modern 20’ Travel Trailer with bunks and a queen bed

Modern 20’ Travel Trailer with bunks and a queen bed
Speedwell
$121 nightly
The price is $133
Jul 13 - Jul 14
Total with taxes and fees
Modern 20’ Travel Trailer with bunks and a queen bed

The Nomad on Norris Lake

The Nomad on Norris Lake
New Tazewell
$343 nightly
The price is $380
Jul 6 - Jul 7
Total with taxes and fees
The Nomad on Norris Lake

One Bedroom Rustic Cabin

One Bedroom Rustic Cabin
Speedwell
$89 nightly
The price is $97
Jun 26 - Jun 27
Total with taxes and fees
One Bedroom Rustic Cabin

Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home
3.0 star property
Williamsburg
$278 nightly
The price is $307
Jun 26 - Jun 27
Total with taxes and fees
Peaceful & Private! Pet-friendly Williamsburg Home

Robertson Ridge Hideaway Cottage

Robertson Ridge Hideaway Cottage
Hinkle
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful place "
United States
Isaac L.
$133 nightly
The price is $146
Jun 28 - Jun 29
Total with taxes and fees
Robertson Ridge Hideaway Cottage

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.
$213 nightly
The price is $236
Jul 1 - Jul 2
Total with taxes and fees
Blissful Bungalow across from LMU campus

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
$118 nightly
The price is $132
Jun 27 - Jun 28
Total with taxes and fees
Quaint Studio APT Near ATV Trails & Norris Lake

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.
$172 nightly
The price is $193
Jul 13 - Jul 14
Total with taxes and fees
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina

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.
$165 nightly
The price is $183
Jul 6 - Jul 7
Total with taxes and fees
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!

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.
$158 nightly
The price is $178
Jul 6 - Jul 7
Total with taxes and fees
Remodeled Western Country Getaway Near Lake & Trails

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.
$252 nightly
The price is $280
Jun 30 - Jul 1
Total with taxes and fees
Calm Country Oasis - Creek, ATV Trls & Norris Lake

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.
$282 nightly
The price is $308
Jun 26 - Jun 27
Total with taxes and fees
Peaceful & Private! Pet-Friendly Williamsburg Home

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.
$239 nightly
The price is $267
Jun 29 - Jun 30
Total with taxes and fees
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

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
$181 nightly
The price is $196
Jul 1 - Jul 2
Total with taxes and fees
Harrogate Hideaway - 5 Min to LMU & Nat`l Park

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, (7 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.
$279 nightly
The price is $314
Jul 1 - Jul 2
Total with taxes and fees
Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's

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.
$320 nightly
The price is $369
Jun 28 - Jun 29
Total with taxes and fees
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

Find out more about Middlesboro

Everything you need to know about Middlesboro vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middlesboro vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middlesboro vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middlesboro vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middlesboro. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Middlesboro in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $225 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middlesboro rentals

At Expedia, we put the best Middlesboro vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middlesboro rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middlesboro vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middlesboro. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

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

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 Mall 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.