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Middlesboro Vacation Rentals

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Check prices for these dates

Tonight
Dec 24 - Dec 25
Tomorrow
Dec 25 - Dec 26
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Middlesboro vacation rentals

2 bedrooms, iron/ironing board, free WiFi, bed sheets
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,

Vacation Home in Middlesboro

4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
10.0 out of 10, Exceptional, (22)
"Great property! Very clean and homey!"
United States
Lillian I.
The price is ￥18,578
￥36,313 total
includes taxes & fees
Dec 28 - Dec 29
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
3 bedrooms, desk, iron/ironing board, travel crib
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

Vacation Home in Middlesboro

Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
9.2 out of 10, Wonderful, (5)
"We enjoyed our stay. "
United States
Emily S.
The price is ￥27,321
￥58,000 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Microwave, oven, stovetop
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU

Vacation Home in Middlesboro

Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
10.0 out of 10, Exceptional, (1)
"Clean"
United States
Phineas S.
The price is ￥24,199
￥50,084 total
includes taxes & fees
Jan 21 - Jan 22, 2026
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
Property grounds
Welcoming 3-bedroom house with AC in charming Middlesboro

Vacation Home in Middlesboro

Welcoming 3-bedroom house with AC in charming Middlesboro
The price is ￥33,097
￥56,279 total
includes taxes & fees
Jan 24 - Jan 25, 2026
Welcoming 3-bedroom house with AC in charming Middlesboro
Miscellaneous
RV/Camper Sites. No Electric

Camping in Speedwell

RV/Camper Sites. No Electric
2.0 star property
The price is ￥4,393
￥9,831 total
includes taxes & fees
Dec 25 - Dec 26
RV/Camper Sites. No Electric
WiFi, bed sheets
Modern 20’ Travel Trailer with bunks and a queen bed

Mobile Home in Speedwell

Modern 20’ Travel Trailer with bunks and a queen bed
2.0 star property
The price is ￥9,367
￥18,719 total
includes taxes & fees
Dec 25 - Dec 26
Modern 20’ Travel Trailer with bunks and a queen bed
Room
2-bedroom apartment in adorable Pineville with AC for relaxing stays

Apartment in Pineville

2-bedroom apartment in adorable Pineville with AC for relaxing stays
2.0 star property
The price is ￥14,988
￥28,570 total
includes taxes & fees
Dec 25 - Dec 26
2-bedroom apartment in adorable Pineville with AC for relaxing stays
Terrace/patio
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina

Vacation Home in Speedwell

Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
9.4 out of 10, Exceptional, (19)
"It was exceptional "
United States
Dennis W.
The price is ￥11,241
￥24,884 total
includes taxes & fees
Dec 28 - Dec 29
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
Interior
One Bedroom Rustic Cabin

Cabin in Speedwell

One Bedroom Rustic Cabin
2.0 star property
The price is ￥6,120
￥13,497 total
includes taxes & fees
Jan 2 - Jan 3, 2026
One Bedroom Rustic Cabin
Exterior
Beautiful Loft in the Woods

Apartment in Harlan

Beautiful Loft in the Woods
10.0 out of 10, Exceptional, (3)
"Beautiful setting. Incredible space well laid out. Owner was very engaging. "
United States
Fred
The price is ￥17,173
￥36,485 total
includes taxes & fees
Dec 28 - Dec 29
Beautiful Loft in the Woods
House (2 Bedrooms) | Interior
Peaceful & Private! Pet-friendly Williamsburg Home

Cottage in Williamsburg

Peaceful & Private! Pet-friendly Williamsburg Home
3.0 star property
The price is ￥15,300
￥47,921 total
includes taxes & fees
Dec 30 - Dec 31
Peaceful & Private! Pet-friendly Williamsburg Home
Exterior
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cottage in Cumberland Gap

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
9.2 out of 10, Wonderful, (42)
"Great location. Easy walk to town and close to hiking areas. Highly recommend. "
United States
Linda O.
The price is ￥15,456
￥32,826 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
TV, fireplace
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!

Cabin in Tazewell

Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
10.0 out of 10, Exceptional, (4)
"Everything was clean and felt like home.host was really nice and I will definitely be staying again."
United States
Nicholas H.
The price is ￥13,489
￥25,273 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
Terrace/patio
Peaceful & Private! Pet-Friendly Williamsburg Home

Vacation Home in Williamsburg

Peaceful & Private! Pet-Friendly Williamsburg Home
2.0 star property
The price is ￥13,739
￥47,102 total
includes taxes & fees
Dec 26 - Dec 27
Peaceful & Private! Pet-Friendly Williamsburg Home
Fridge, microwave, oven, stovetop
Harrogate Home Mountain View’s Dog Friendly

Vacation Home in Harrogate

Harrogate Home Mountain View’s Dog Friendly
10.0 out of 10, Exceptional, (22)
"Great location with friendly neighbors!"
United States
Evan C.
The price is ￥24,589
￥46,725 total
includes taxes & fees
Dec 29 - Dec 30
Harrogate Home Mountain View’s Dog Friendly
Living area
Pleasant 2-bedroom apartment with AC in Barbourville

Apartment in Barbourville

Pleasant 2-bedroom apartment with AC in Barbourville
2.0 star property
The price is ￥20,139
￥56,485 total
includes taxes & fees
Dec 25 - Dec 26
Pleasant 2-bedroom apartment with AC in Barbourville
Fridge, microwave, oven, stovetop
Tranquil Haven MTN Retreat, 3-bedroom, 2-bath, WIFI, AC in Beautiful Tazewell

Vacation Home in Tazewell

Tranquil Haven MTN Retreat, 3-bedroom, 2-bath, WIFI, AC in Beautiful Tazewell
2.0 star property
10.0 out of 10, Exceptional, (7)
"Great place that is well stocked and close to amenities as well. Spacious house with an awesome porch with a view!"
United States
Brendan W.
The price is ￥31,068
￥68,186 total
includes taxes & fees
Dec 25 - Dec 26
Tranquil Haven MTN Retreat, 3-bedroom, 2-bath, WIFI, AC in Beautiful Tazewell
Comfort House | Private kitchen | Full-size fridge, microwave, oven, stovetop
The House on Park Avenue

Vacation Home in Pineville

The House on Park Avenue
3.5 star property
The price is ￥45,398
￥62,380 total
includes taxes & fees
Dec 26 - Dec 27
The House on Park Avenue
Property grounds
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky

Vacation Home in Pineville

Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
10.0 out of 10, Exceptional, (2)
"We stayed here for a wedding weekend in Pineville, KY, and it was absolutely perfect from start to finish. The home was spotless, cozy, and had everything we could possibly need. The beds were so comfortable, and we instantly felt at home the moment we walked in.What truly set this stay apart was the host’s kindness and above-and-beyond hospitality. We got lost in the middle of the night trying to find the property, and the host stayed on the phone with us, patiently guiding us right to the...
United States
Samantha P.
The price is ￥24,870
￥46,176 total
includes taxes & fees
Dec 25 - Dec 26
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Living area
Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville

Vacation Home in Pineville

Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville
10.0 out of 10, Exceptional, (1)
"Well cared for property with nice upgrades! Perfect for our stay, everything we needed, and accommodating. "
United States
Hope C.
The price is ￥23,886
￥35,109 total
includes taxes & fees
Dec 25 - Dec 26
Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville
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

10/10 Excellent
"Great staff, clean room, upgraded room, recently renovated room, nice Mountain View. "
Ashley 1-night trip
Posted 3 days ago
Days Inn by Wyndham Jellico - Tennessee State Line

Find out more about Middlesboro

Search for holiday rentals in Middlesboro on Expedia! You can easily find your home rentals, villas, holiday apartments in Middlesboro using one of the methods below:

  • View our selection of featured holiday rentals in Middlesboro
  • Use the map to find apartments and other holiday homes in the Middlesboro neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middlesboro while they last

Look no further and take a look at our great range of rental properties in Middlesboro!

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?

Lakefront w/ Private Dock, 7 BR, Free Kayaks, Firepit, Hot Tub: 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 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a hot tub.

How many vacation rentals are there in Middlesboro?

With 5 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.