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

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Middlesboro vacation rentals

A dining area with a table set for four, a ceiling fan, and a sign above reading 'BE OUR GUEST'.

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

Private bungalow close to LMU, ARH, Cumberland Gap
Middlesboro
8.0 out of 10, Very good, (1 review)
"This house was conveniently located. Upstairs bedroom was hot but everything else was nice."
United States
Leann L.
$290 nightly
The price is $334
Oct 19 - Oct 20
Total with taxes and fees
Private bungalow close to LMU, ARH, Cumberland Gap
A living room with a stone fireplace, wooden walls, a sofa, a coffee table, and a TV mounted on the wall.

2. Gorgeous 4-bedroom house in Middlesboro KY with WiFi, AC. Minutes from LMU

Gorgeous 4-bedroom house in Middlesboro KY with WiFi, AC. Minutes from LMU
Middlesboro
10.0 out of 10, Exceptional, (19 reviews)
"Lots of room. Clean. Good host."
United States
Konnie D.
$367 nightly
The price is $405
Oct 28 - Oct 29
Total with taxes and fees
Gorgeous 4-bedroom house in Middlesboro KY with WiFi, AC. Minutes from LMU
A bedroom with a bed, pillows, a nightstand, a lamp, a window with blinds, and a kitchen area with a refrigerator.

3. 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, (8 reviews)
"We enjoyed our stay. "
United States
Emily S.
$341 nightly
The price is $394
Oct 16 - Oct 17
Total with taxes and fees
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
A brick house with a covered porch, a front door, and a small garden area with potted plants.

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
Oct 18 - Oct 19
Total with taxes and fees
Welcoming 3-bedroom house with AC in charming Middlesboro
A living room with a TV on a wooden stand, a white chair, a small table, and a sofa.

5. 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.
$348 nightly
The price is $401
Nov 5 - Nov 6
Total with taxes and fees
House close to ARH Hospital, Tackett Creek & LMU!
Private kitchen

6. 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, (20 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
Oct 18 - Oct 19
Total with taxes and fees
Harrogate Hideaway - 5 Min to LMU & Nat`l Park
A rustic wooden building with a porch, stone pillars, and potted plants.

7. Luxury Brooklyn St APT - Near LMU & Nat’l Park

Luxury Brooklyn St APT - Near LMU & Nat’l Park
Cumberland Gap
9.8 out of 10, Exceptional, (32 reviews)
"Great location So close to so much hiking."
United States
Theresa l.
$190 nightly
The price is $212
Oct 18 - Oct 19
Total with taxes and fees
Luxury Brooklyn St APT - Near LMU & Nat’l Park
An aerial view of a campus with multiple buildings, a central tower, and a large open grassy area.

8. Blissful Bungalow across from LMU campus

Blissful Bungalow across from LMU campus
Harrogate
9.6 out of 10, Exceptional, (43 reviews)
"Very convenient to everything we needed to do, very clean and neat"
United States
Brandi L.
$200 nightly
The price is $222
Oct 21 - Oct 22
Total with taxes and fees
Blissful Bungalow across from LMU campus
A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a sign reading "EVERYDAY COOKING".

9. Harrogate Home Mountain View’s Dog Friendly

Harrogate Home Mountain View’s Dog Friendly
Harrogate
10.0 out of 10, Exceptional, (31 reviews)
"Great place to stay. "
United States
Jodi D.
$237 nightly
The price is $271
Oct 21 - Oct 22
Total with taxes and fees
Harrogate Home Mountain View’s Dog Friendly
A wooden deck with a railing, a brick building, and a door with a window.

10. 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, (12 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
Oct 16 - Oct 17
Total with taxes and fees
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
A long, narrow hallway with exposed wooden beams and a concrete floor. There is a door on the right and a window on the left.

11. One Bedroom Rustic Cabin

One Bedroom Rustic Cabin
Speedwell
$89 nightly
The price is $97
Oct 16 - Oct 17
Total with taxes and fees
One Bedroom Rustic Cabin
A dining area with a wooden table set for four, a lamp, and framed artwork on the walls.

12. 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
Oct 18 - Oct 19
Total with taxes and fees
2-bedroom loft apartment in adorable Pineville close to Pine Mountain State Park
A covered outdoor deck with wooden flooring and metal chairs.

13. Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home
3.0 star property
Williamsburg
$279 nightly
The price is $307
Oct 18 - Oct 19
Total with taxes and fees
Peaceful & Private! Pet-friendly Williamsburg Home
A covered outdoor deck with wooden flooring and metal chairs.

14. Peaceful & Private! Pet-Friendly Williamsburg Home

Peaceful & Private! Pet-Friendly Williamsburg Home
Williamsburg
10.0 out of 10, Exceptional, (5 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
Oct 18 - Oct 19
Total with taxes and fees
Peaceful & Private! Pet-Friendly Williamsburg Home
A room with a large window offering a view of a well-maintained garden with trees and grass.

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

Calm Country Oasis - Creek, ATV Trls & Norris Lake
Speedwell
9.6 out of 10, Exceptional, (27 reviews)
"Loved the creek and inside decor. Roomy house!"
United States
Sandra
$236 nightly
The price is $262
Oct 18 - Oct 19
Total with taxes and fees
Calm Country Oasis - Creek, ATV Trls & Norris Lake
Living Room

16. Outback Behind the Barn

Outback Behind the Barn
Ewing
$124 nightly
The price is $137
Oct 16 - Oct 17
Total with taxes and fees
Outback Behind the Barn
A spacious living room with wooden beams, leather sofas, a wooden coffee table, and a mounted deer head.

17. 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
Oct 17 - Oct 18
Total with taxes and fees
Peaceful ‘Mountain Cabin’ w/ Views in Williamsburg
An outdoor patio with a wooden table and wicker chairs.

18. 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
Oct 16 - Oct 17
Total with taxes and fees
The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!
A covered outdoor seating area with a sofa, chairs, and planters.

19. LMU Pine Mtn State Park Cumberland Gap Laurel Cove

LMU Pine Mtn State Park Cumberland Gap Laurel Cove
Pineville
10.0 out of 10, Exceptional, (1 review)
"Well cared for property with nice upgrades! Perfect for our stay, everything we needed, and accommodating. "
United States
Hope C.
$308 nightly
The price is $355
Nov 5 - Nov 6
Total with taxes and fees
LMU Pine Mtn State Park Cumberland Gap Laurel Cove
A compact RV interior with a kitchenette, a dining area, and a sleeping berth.

20. Modern 20’ Travel Trailer with bunks and a queen bed

Modern 20’ Travel Trailer with bunks and a queen bed
Speedwell
2.0 out of 10, (1 review)
$108 nightly
The price is $119
Oct 26 - Oct 27
Total with taxes and fees
Modern 20’ Travel Trailer with bunks and a queen bed
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

Quality Inn Harlan

Quality Inn Harlan

10/10 Excellent
"The staff was very friendly and nice and constantly make sure you had clean sheets and towels, and great breakfast every morning multiple things to choose from hot breakfast. I’ll definitely stay there again."
Beau 3-night trip
Posted 6 hours ago
Quality Inn Harlan

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 $172 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?

Brand New, Spacious 9 bedroom, 9 1/2 bath Waterfront house in Lakeside Estates: This vacation home rental near Middlesboro offers a patio, a hot tub, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 9 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, 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 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.