An aerial view of a town surrounded by mountains, with a mix of residential and commercial buildings, and a highway running through the center.

Middlesboro Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Middlesboro vacation rentals

Dining

1. Private bungalow close to LMU, ARH, Cumberland Gap

Private bungalow close to LMU, ARH, Cumberland Gap
Middlesboro
$290 nightly
The price is $334
Aug 13 - Aug 14
Total with taxes and fees
Private bungalow close to LMU, ARH, Cumberland Gap
Desk, iron/ironing board, WiFi, bed sheets

2. 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
9.0 out of 10, Wonderful, (6 reviews)
"We enjoyed our stay. "
United States
Emily S.
$336 nightly
The price is $388
Sep 7 - Sep 8
Total with taxes and fees
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Desk, WiFi, bed sheets

3. House close to ARH Hospital, Tackett Creek & LMU!

House close to ARH Hospital, Tackett Creek & 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.
$326 nightly
The price is $376
Aug 20 - Aug 21
Total with taxes and fees
House close to ARH Hospital, Tackett Creek & LMU!
Exterior

4. 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.
$339 nightly
The price is $391
Aug 11 - Aug 12
Total with taxes and fees
Welcoming 3-bedroom house with AC in charming Middlesboro
Coffee/tea maker, fridge, microwave, oven

5. 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, (18 reviews)
"Absolutely perfect!Plenty of space, beds were great and so comfortable. Well equipped and the best part so quiet!!! Perfect location for parents visiting LMU students, I highly recommend!"
United States
Amy C.
$180 nightly
The price is $195
Aug 11 - Aug 12
Total with taxes and fees
Harrogate Hideaway - 5 Min to LMU & Nat`l Park
Exterior

6. Blissful Bungalow across from LMU campus

Blissful Bungalow across from LMU campus
Harrogate
9.6 out of 10, Exceptional, (39 reviews)
"Very convenient to everything we needed to do, very clean and neat"
United States
Brandi L.
$200 nightly
The price is $222
Aug 11 - Aug 12
Total with taxes and fees
Blissful Bungalow across from LMU campus
Coffee/tea maker, fridge, microwave, oven

7. Harrogate Home Mountain View’s Dog Friendly

Harrogate Home Mountain View’s Dog Friendly
Harrogate
10.0 out of 10, Exceptional, (26 reviews)
"Great place to stay. "
United States
Jodi D.
$237 nightly
The price is $252
Aug 18 - Aug 19
Total with taxes and fees
Harrogate Home Mountain View’s Dog Friendly
Property grounds

8. 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, (9 reviews)
"Clean and quiet place to stay when visiting the area. Will definitely consider this place again when we visit Pineville again! "
United States
seth r.
$268 nightly
The price is $296
Aug 11 - Aug 12
Total with taxes and fees
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Interior

9. Calm Country Oasis - Creek, ATV Trls & Norris Lake

Calm Country Oasis - Creek, ATV Trls & Norris Lake
Speedwell
9.6 out of 10, Exceptional, (26 reviews)
"Clean home, responsive host, beautiful location, family friendly."
United States
Anna S.
$236 nightly
The price is $261
Sep 1 - Sep 2
Total with taxes and fees
Calm Country Oasis - Creek, ATV Trls & Norris Lake
Outdoor dining

10. 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, (6 reviews)
"Such a cute little place we have stayed twice already"
United States
Cassie S.
$325 nightly
The price is $375
Aug 11 - Aug 12
Total with taxes and fees
The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!
Dining

11. 2-bedroom loft apartment in adorable Pineville close to Pine Mountain State Park

2-bedroom loft apartment in adorable Pineville close to Pine Mountain State Park
Pineville
10.0 out of 10, Exceptional, (1 review)
"We stayed for the 95th Mountain Laurel Festival and LOVED the location, access to all festival activities, and how easy it was to communicate with the renter. We hope to make this a tradition and will stay here again!"
United States
jennifer w.
$259 nightly
The price is $298
Aug 11 - Aug 12
Total with taxes and fees
2-bedroom loft apartment in adorable Pineville close to Pine Mountain State Park
TV, fireplace, books

12. 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.
$314 nightly
The price is $346
Aug 11 - Aug 12
Total with taxes and fees
Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg
Terrace/patio

13. 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, (12 reviews)
"The hosts were wonderful, very accommodating and helpful through our stay. The cabin was clean and nicely put together for a relaxing visit."
United States
Sharon W.
$155 nightly
The price is $159
Aug 11 - Aug 12
Total with taxes and fees
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
Interior

14. One Bedroom Rustic Cabin

One Bedroom Rustic Cabin
Speedwell
$89 nightly
The price is $91
Aug 11 - Aug 12
Total with taxes and fees
One Bedroom Rustic Cabin
Interior

15. The Highlands Cabin ~ Norris Lake Views & Modern Comfort

The Highlands Cabin ~ Norris Lake Views & Modern Comfort
New Tazewell
10.0 out of 10, Exceptional, (7 reviews)
"The cabin was clean, cozy, and overall amazing! "
United States
Fannie
$205 nightly
The price is $210
Aug 11 - Aug 12
Total with taxes and fees
The Highlands Cabin ~ Norris Lake Views & Modern Comfort
Exterior detail

16. Min. to Laurel Cove, LMU & Union, & Bell Theater

Min. to Laurel Cove, LMU & Union, & Bell Theater
Pineville
4.8 out of 10, (3 reviews)
"I did not stay at this property due to a double booking. I stayed at a nearby house that needs to be cleaned better, specially the floors, a shower curtain needs to be added to the beautiful update in bathroom, some plates woukd be nice. House rules and check in, check out procedures, places to visit and eat nearby would have been helpful to have posted at the house. Overall was a decent place to stay, quiet neighborhood. I would at least consider staying again."
United States
Stephanie F.
$233 nightly
The price is $269
Aug 11 - Aug 12
Total with taxes and fees
Min. to Laurel Cove, LMU & Union, & Bell Theater
Terrace/patio

17. 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
9.2 out of 10, Wonderful, (25 reviews)
"Nice place. Everything you need and more"
United States
Jeff L.
$160 nightly
The price is $167
Aug 11 - Aug 12
Total with taxes and fees
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
Interior

18. The Lodge Cabin ~Norris Lake Views and Mountain Backdrops

The Lodge Cabin ~Norris Lake Views and Mountain Backdrops
New Tazewell
10.0 out of 10, Exceptional, (5 reviews)
$205 nightly
The price is $210
Aug 11 - Aug 12
Total with taxes and fees
The Lodge Cabin ~Norris Lake Views and Mountain Backdrops
Terrace/patio

19. 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 $311
Aug 22 - Aug 23
Total with taxes and fees
Peaceful & Private! Pet-Friendly Williamsburg Home
Coffee/tea maker, fridge, microwave, oven

20. Remodeled Western Country Getaway Near Lake & Trails

Remodeled Western Country Getaway Near Lake & Trails
LaFollette
10.0 out of 10, Exceptional, (6 reviews)
$166 nightly
The price is $187
Aug 13 - Aug 14
Total with taxes and fees
Remodeled Western Country Getaway Near Lake & Trails
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
"No one was in office but a note was on the door - be back soon. Waited only a few minutes. Did not turn on the TV but the internet was fine. McDonalds at bottom of the hill and can be entered from motel drive, avoiding going back to the street. Did not do breakfast, can't rate it. Park in front of your door, which I like. It was comfortable."
John F 1-night trip
Posted 3 days ago
Days Inn by Wyndham Jellico - Tennessee State Line

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 $167 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?

Beautiful Norris Lake WATERFRONT. Near Flat Hollow Marina. Private dock.: This vacation home rental 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, Cumberland Gap National Historical Park and Middlesboro Mall 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.