Photo by Alexis Wyrick

Middlesboro Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
21 Dec - 22 Dec
Tomorrow
22 Dec - 23 Dec
Next weekend
26 Dec - 28 Dec
In two weeks
2 Jan - 4 Jan

Our top choices for Middlesboro holiday rentals

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

Holiday 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 HK$926
HK$1,810 total
includes taxes & fees
28 Dec - 29 Dec
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
3 bedrooms, desk, iron/ironing board, travel cot
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

Holiday 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 HK$1,362
HK$2,891 total
includes taxes & fees
23 Dec - 24 Dec
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

Holiday 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 HK$2,584
HK$4,230 total
includes taxes & fees
22 Dec - 23 Dec
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
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 HK$459
HK$924 total
includes taxes & fees
22 Dec - 23 Dec
Modern 20’ Travel Trailer with bunks and a queen bed
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 HK$856
HK$1,810 total
includes taxes & fees
22 Dec - 23 Dec
Beautiful Loft in the Woods
Terrace/patio
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina

Holiday 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 HK$560
HK$1,240 total
includes taxes & fees
23 Dec - 24 Dec
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
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 HK$770
HK$1,652 total
includes taxes & fees
22 Dec - 23 Dec
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Fridge, microwave, oven, stovetop
Tranquil Haven MTN Retreat, 3-bedroom, 2-bath, WIFI, AC in Beautiful Tazewell

Holiday 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 HK$1,548
HK$3,398 total
includes taxes & fees
22 Dec - 23 Dec
Tranquil Haven MTN Retreat, 3-bedroom, 2-bath, WIFI, AC in Beautiful Tazewell
Exterior
Luxury Brooklyn St APT - Near LMU & Nat’l Park

Apartment in Cumberland Gap

Luxury Brooklyn St APT - Near LMU & Nat’l Park
9.6 out of 10, Exceptional, (25)
"This apartment was perfect for my husband and I and 2 adult children. It was right downtown Cumberland Gap with great views and a cute patio to enjoy morning coffee. It had everything we needed and was extremely clean. The hosts was easy to communicate with and provided all the information we needed to enjoy our stay. "
United States
kim s.
The price is HK$786
HK$1,573 total
includes taxes & fees
22 Dec - 23 Dec
Luxury Brooklyn St APT - Near LMU & Nat’l Park
Fridge, microwave, oven, stovetop
Harrogate Home Mountain View’s Dog Friendly

Holiday 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 HK$1,226
HK$2,337 total
includes taxes & fees
27 Dec - 28 Dec
Harrogate Home Mountain View’s Dog Friendly
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 HK$714
HK$1,307 total
includes taxes & fees
22 Dec - 23 Dec
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
Property grounds
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky

Holiday 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 HK$1,240
HK$2,301 total
includes taxes & fees
22 Dec - 23 Dec
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Property grounds
Lake Front ★ No Wake w/ Dock ★ Gameroom ★ Carved FirePit ★ 2nd House Available

Holiday Home in LaFollette

Lake Front ★ No Wake w/ Dock ★ Gameroom ★ Carved FirePit ★ 2nd House Available
10.0 out of 10, Exceptional, (46)
"House was just as advertised and hosts were very helpful during the entire stay. Would highly recommend the house and hosts. "
United States
Tom S.
The price is HK$1,890
HK$5,655 total
includes taxes & fees
22 Dec - 23 Dec
Lake Front ★ No Wake w/ Dock ★ Gameroom ★ Carved FirePit ★ 2nd House Available
Terrace/patio
Peaceful & Private! Pet-Friendly Williamsburg Home

Holiday Home in Williamsburg

Peaceful & Private! Pet-Friendly Williamsburg Home
2.0 star property
The price is HK$685
HK$2,365 total
includes taxes & fees
22 Dec - 23 Dec
Peaceful & Private! Pet-Friendly Williamsburg Home
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 HK$1,004
HK$2,815 total
includes taxes & fees
22 Dec - 23 Dec
Pleasant 2-bedroom apartment with AC in Barbourville
Interior
One Bedroom Rustic Cabin

Cabin in Speedwell

One Bedroom Rustic Cabin
2.0 star property
The price is HK$305
HK$673 total
includes taxes & fees
22 Dec - 23 Dec
One Bedroom Rustic Cabin
Private kitchen
The House on Park Avenue

Holiday Home in Pineville

The House on Park Avenue
3.5 star property
The price is HK$2,263
HK$3,109 total
includes taxes & fees
22 Dec - 23 Dec
The House on Park Avenue
Living area
Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville

Holiday 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 HK$1,471
HK$2,093 total
includes taxes & fees
24 Dec - 25 Dec
Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville
Exterior
Jackson MTN Retreat 3-bedroom entire HOME in Harrogate-Near LMU & Bowling alley

Holiday Home in Harrogate

Jackson MTN Retreat 3-bedroom entire HOME in Harrogate-Near LMU & Bowling alley
2.0 star property
The price is HK$1,548
HK$3,507 total
includes taxes & fees
24 Dec - 25 Dec
Jackson MTN Retreat 3-bedroom entire HOME in Harrogate-Near LMU & Bowling alley
Private kitchen
3-Bedroom Cottage, Peaceful setting, Close to Parks, 2 min. from Bell Theatre

Holiday Home in Pineville

3-Bedroom Cottage, Peaceful setting, Close to Parks, 2 min. from Bell Theatre
4.8 out of 10, (3)
"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.
The price is HK$568
HK$1,690 total
includes taxes & fees
22 Dec - 23 Dec
3-Bedroom Cottage, Peaceful setting, Close to Parks, 2 min. from Bell Theatre
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

Family Affair, room 4 30, 15 Beds, 2 FULL Kitchens!!! Huge dock w 2 boat slips

Family Affair, room 4 30, 15 Beds, 2 FULL Kitchens!!! Huge dock w 2 boat slips

10/10 Excellent
"Every December our family rents a cabin for a long weekend to be together. Family affair was the best we’ve ever picked. The house is well-built, well-stocked and very clean. Since it’s winter, we did not enjoy the lake, but I can only imagine the additional fun on the water!"
Christi S. 3-night trip
Posted 3 days ago
Family Affair, room 4 30, 15 Beds, 2 FULL Kitchens!!! Huge dock w 2 boat slips

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 holiday rentals in Middlesboro?

Yes, there are holiday rentals close to the most popular sights in Middlesboro, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that Middlesboro has to offer?

Lakefront w/ Private Dock, 7 BR, Free Kayaks, Firepit, Hot Tub: This holiday home rental outside of Middlesboro is located on a lake, and has a balcony, a selection of games and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals are there in Middlesboro?

With 5 Expedia holiday rentals, you're guaranteed 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 holiday rental in Middlesboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middlesboro. Holiday rentals feature amenities such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for families.