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
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Middlesboro vacation rentals

A portable barbecue grill with a black and green design, mounted on a metal stand with adjustable legs.

1. 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, (20 reviews)
"Lots of room. Clean. Good host."
United States
Konnie D.
The price is SAR 619
SAR 1,403 total
includes taxes & fees
19 Nov - 20 Nov
Gorgeous 4-bedroom house in Middlesboro KY with WiFi, AC. Minutes from LMU
An outdoor patio with a wooden ceiling, string lights, a sofa, chairs, and a table.

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
9.2 out of 10, Wonderful, (9 reviews)
"We enjoyed our stay. "
United States
Emily S.
The price is SAR 523
SAR 1,116 total
includes taxes & fees
15 Nov - 16 Nov
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.

3. 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 SAR 626
SAR 1,244 total
includes taxes & fees
15 Nov - 16 Nov
Welcoming 3-bedroom house with AC in charming Middlesboro
A single-story house with a front porch, a door with a wreath, and a number '303' on the front.

4. 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.
The price is SAR 547
SAR 1,107 total
includes taxes & fees
15 Nov - 16 Nov
Private bungalow close to LMU, ARH, Cumberland Gap
A kitchen with light blue cabinets, a black microwave, a sink, and a stove.

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.
The price is SAR 506
SAR 1,145 total
includes taxes & fees
15 Dec - 16 Dec
House close to ARH Hospital, Tackett Creek & LMU!
A single-story house with a porch, a mailbox, and a small garden.

6. Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Cumberland Gap
9.4 out of 10, Exceptional, (52 reviews)
"The house was nice and clean and ready for us. When we checked in, the location was absolutely perfect from downtown, Everything worked out the way it should be. If we go back to Cumberland Gap, which I hope we will we will try to stay in the same location."
United States
JOHN H.
The price is SAR 372
SAR 767 total
includes taxes & fees
19 Nov - 20 Nov
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Private kitchen

7. 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.
The price is SAR 372
SAR 697 total
includes taxes & fees
15 Nov - 16 Nov
Harrogate Hideaway - 5 Min to 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, (46 reviews)
"The house is beautiful and cozy on the inside. Communication with the host was quick and efficient. We will definitely be back."
United States
Eva M.
The price is SAR 409
SAR 776 total
includes taxes & fees
13 Dec - 14 Dec
Blissful Bungalow across from LMU campus
A rustic wooden building with a porch, stone pillars, and potted plants.

9. 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, (35 reviews)
"Great location So close to so much hiking."
United States
Theresa l.
The price is SAR 372
SAR 720 total
includes taxes & fees
21 Nov - 22 Nov
Luxury Brooklyn St APT - Near LMU & Nat’l Park
A wooden deck with two chairs and a small table, overlooking a green landscape.

10. Harrogate Home Mountain View’s Dog Friendly

Harrogate Home Mountain View’s Dog Friendly
Harrogate
10.0 out of 10, Exceptional, (32 reviews)
"Great place to stay. "
United States
Jodi D.
The price is SAR 591
SAR 1,070 total
includes taxes & fees
15 Nov - 16 Nov
Harrogate Home Mountain View’s Dog Friendly
A wooden deck with a railing, a brick building, and a door with a window.

11. 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, (13 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.
The price is SAR 638
SAR 1,101 total
includes taxes & fees
15 Nov - 16 Nov
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
A campsite with a fire pit, picnic table, and chairs by a river.

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

Calm Country Oasis - Creek, ATV Trls & Norris Lake
Speedwell
9.6 out of 10, Exceptional, (30 reviews)
"Loved the creek and inside decor. Roomy house!"
United States
Sandra
The price is SAR 409
SAR 906 total
includes taxes & fees
15 Nov - 16 Nov
Calm Country Oasis - Creek, ATV Trls & Norris Lake
An outdoor patio with a wooden table and wicker chairs.

13. Park Ave Laurel Cove, Bell Theatre & LMU

Park Ave Laurel Cove, Bell Theatre & LMU
Pineville
9.4 out of 10, Exceptional, (6 reviews)
"Such a cute little place we have stayed twice already"
United States
Cassie S.
The price is SAR 709
SAR 1,345 total
includes taxes & fees
15 Nov - 16 Nov
Park Ave Laurel Cove, Bell Theatre & LMU
A covered deck with wicker furniture and a glass table.

14. Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home
3.0 star property
Williamsburg
The price is SAR 473
SAR 1,154 total
includes taxes & fees
15 Nov - 16 Nov
Peaceful & Private! Pet-friendly Williamsburg Home
A kitchen with a brick wall, stainless steel appliances, white cabinets, and a wooden table.

15. 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.
The price is SAR 486
SAR 1,070 total
includes taxes & fees
15 Nov - 16 Nov
2-bedroom loft apartment in adorable Pineville close to Pine Mountain State Park
A covered outdoor seating area with a sofa, chairs, and planters.

16. 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.
The price is SAR 558
SAR 1,205 total
includes taxes & fees
15 Nov - 16 Nov
LMU Pine Mtn State Park Cumberland Gap Laurel Cove
An outdoor patio with a pergola, four wicker chairs, a round table, and a view of a green landscape.

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, (31 reviews)
"Our stay was great! Great location and enough bedrooms for our 5 guests at an amazing price point. The host was very responsive as well! Will be staying again."
United States
Rachel W.
The price is SAR 345
SAR 657 total
includes taxes & fees
16 Nov - 17 Nov
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
A wooden deck with a rocking chair and a wicker sofa.

18. 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, (14 reviews)
"Very nice cabin, comfortable and homey."
United States
Carla C.
The price is SAR 357
SAR 588 total
includes taxes & fees
15 Nov - 16 Nov
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
A covered deck with wicker furniture and a glass table.

19. Peaceful & Private! Pet-Friendly Williamsburg Home

Peaceful & Private! Pet-Friendly Williamsburg Home
Williamsburg
10.0 out of 10, Exceptional, (6 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 SAR 330
SAR 1,117 total
includes taxes & fees
15 Nov - 16 Nov
Peaceful & Private! Pet-Friendly Williamsburg Home
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and a grey wooden floor.

20. Welcome to The Classic Corner—a freshly renovated unique apartment.

Welcome to The Classic Corner—a freshly renovated unique apartment.
Barbourville
9.0 out of 10, Wonderful, (4 reviews)
"Easy check in process and very clean."
United States
Jackson H.
The price is SAR 436
SAR 992 total
includes taxes & fees
15 Nov - 16 Nov
Welcome to The Classic Corner—a freshly renovated unique apartment.
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

Pine Mountain State Resort Park

Pine Mountain State Resort Park

10/10 Excellent
"Great stay for nature lovers. Balcony nice feature."
Peter 1-night trip
Posted 2 days ago
Pine Mountain State Resort Park

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.