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Middlesboro Holiday Rentals

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Check prices for these dates

Tonight
3 Jan - 4 Jan
Tomorrow
4 Jan - 5 Jan
Next weekend
9 Jan - 11 Jan
In two weeks
16 Jan - 18 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,

4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,

4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
Middlesboro
10.0 out of 10, Exceptional, (23)
"Very nice and extra clean great time"
United States
Johnny C.
The price is HK$927
HK$1,785 total
includes taxes & fees
7 Jan - 8 Jan
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
Exterior
3-bedroom home away from home in Middesboro. A family friendly environment.

3-bedroom home away from home in Middesboro. A family friendly environment.

3-bedroom home away from home in Middesboro. A family friendly environment.
2.0 star property
Middlesboro
The price is HK$835
HK$1,307 total
includes taxes & fees
1 Feb - 2 Feb
3-bedroom home away from home in Middesboro. A family friendly environment.
3 bedrooms, desk, iron/ironing board, travel cot
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.

Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Middlesboro
9.2 out of 10, Wonderful, (5)
"We enjoyed our stay. "
United States
Emily S.
The price is HK$1,363
HK$2,893 total
includes taxes & fees
7 Jan - 8 Jan
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

Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU

Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
Middlesboro
10.0 out of 10, Exceptional, (1)
"Clean"
United States
Phineas S.
The price is HK$1,831
HK$3,281 total
includes taxes & fees
3 Feb - 4 Feb
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
Property grounds
Welcoming 3-bedroom house with AC in charming Middlesboro

Welcoming 3-bedroom house with AC in charming Middlesboro

Welcoming 3-bedroom house with AC in charming Middlesboro
Middlesboro
The price is HK$1,247
HK$2,345 total
includes taxes & fees
25 Jan - 26 Jan
Welcoming 3-bedroom house with AC in charming Middlesboro
WiFi, bed sheets
Modern 20’ Travel Trailer with bunks and a queen bed

Modern 20’ Travel Trailer with bunks and a queen bed

Modern 20’ Travel Trailer with bunks and a queen bed
2.0 star property
Speedwell
The price is HK$709
HK$1,205 total
includes taxes & fees
3 Feb - 4 Feb
Modern 20’ Travel Trailer with bunks and a queen bed
Miscellaneous
RV/Camper Sites. No Electric

RV/Camper Sites. No Electric

RV/Camper Sites. No Electric
2.0 star property
Speedwell
The price is HK$305
HK$586 total
includes taxes & fees
15 Jan - 16 Jan
RV/Camper Sites. No Electric
TV, fireplace
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!

Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!

Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
Tazewell
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$666
HK$1,253 total
includes taxes & fees
14 Jan - 15 Jan
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
Exterior
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Cumberland Gap
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$771
HK$1,654 total
includes taxes & fees
8 Jan - 9 Jan
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Interior
One Bedroom Rustic Cabin

One Bedroom Rustic Cabin

One Bedroom Rustic Cabin
2.0 star property
Speedwell
The price is HK$305
HK$673 total
includes taxes & fees
7 Jan - 8 Jan
One Bedroom Rustic Cabin
Exterior
Beautiful Loft in the Woods

Beautiful Loft in the Woods

Beautiful Loft in the Woods
Harlan
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$857
HK$1,812 total
includes taxes & fees
4 Jan - 5 Jan
Beautiful Loft in the Woods
Interior
Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home

Peaceful & Private! Pet-friendly Williamsburg Home
3.0 star property
Williamsburg
The price is HK$763
HK$2,390 total
includes taxes & fees
11 Jan - 12 Jan
Peaceful & Private! Pet-friendly Williamsburg Home
Terrace/patio
The Highlands Cabin Retreat at Norris Lake

The Highlands Cabin Retreat at Norris Lake

The Highlands Cabin Retreat at Norris Lake
2.0 star property
New Tazewell
10.0 out of 10, Exceptional, (2)
"The cabin was clean, cozy, and overall amazing! "
United States
Fannie
The price is HK$904
HK$1,608 total
includes taxes & fees
4 Jan - 5 Jan
The Highlands Cabin Retreat at Norris Lake
Property grounds
Calm Country Oasis - Creek, ATV Trls & Norris Lake

Calm Country Oasis - Creek, ATV Trls & Norris Lake

Calm Country Oasis - Creek, ATV Trls & Norris Lake
Speedwell
9.4 out of 10, Exceptional, (22)
"The hosts was great to communicate with. Everything was so smooth. There is a Dollar General down the road if you need quick groceries. House was clean and in good shape. We loved the creek behind the house. "
United States
Autumn
Calm Country Oasis - Creek, ATV Trls & Norris Lake
Exterior
Luxury Brooklyn St APT - Near LMU & Nat’l Park

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

Luxury Brooklyn St APT - Near LMU & Nat’l Park
Cumberland Gap
9.6 out of 10, Exceptional, (25)
"This place was just as described and perfect for our stay!"
United States
Melissa M.
The price is HK$771
HK$1,549 total
includes taxes & fees
4 Jan - 5 Jan
Luxury Brooklyn St APT - Near LMU & Nat’l Park
Terrace/patio
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

Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
Speedwell
9.4 out of 10, Exceptional, (19)
"It was exceptional "
United States
Dennis W.
The price is HK$421
HK$1,082 total
includes taxes & fees
5 Jan - 6 Jan
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
Fridge, microwave, oven, stovetop
Waterfront Retreat, Sleeps 12・Fireplace・Grill・Dock

Waterfront Retreat, Sleeps 12・Fireplace・Grill・Dock

Waterfront Retreat, Sleeps 12・Fireplace・Grill・Dock
2.0 star property
Rock Harbor
The price is HK$1,261
HK$4,109 total
includes taxes & fees
15 Jan - 16 Jan
Waterfront Retreat, Sleeps 12・Fireplace・Grill・Dock
Outdoor spa tub
Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's

Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's

Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's
Sharps Chapel
10.0 out of 10, Exceptional, (5)
"This was definitely the most romantic VRBO we’ve stayed at!!! Very clean, and the view from all of the balconies was incredible!!! "
United States
Stan N.
The price is HK$1,121
HK$2,326 total
includes taxes & fees
15 Jan - 16 Jan
Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's
Terrace/patio
Peaceful & Private! Pet-Friendly Williamsburg Home

Peaceful & Private! Pet-Friendly Williamsburg Home

Peaceful & Private! Pet-Friendly Williamsburg Home
2.0 star property
Williamsburg
The price is HK$685
HK$2,349 total
includes taxes & fees
14 Jan - 15 Jan
Peaceful & Private! Pet-Friendly Williamsburg Home
Fridge, microwave, oven, stovetop
Harrogate Home Mountain View’s Dog Friendly

Harrogate Home Mountain View’s Dog Friendly

Harrogate Home Mountain View’s Dog Friendly
Harrogate
10.0 out of 10, Exceptional, (22)
"Great location with friendly neighbors!"
United States
Evan C.
The price is HK$1,227
HK$2,340 total
includes taxes & fees
4 Jan - 5 Jan
Harrogate Home Mountain View’s Dog Friendly
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

Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG

10/10 Excellent
"Courteous staff and clean room "
alexandria 1-night trip
Posted 21 hours ago
Holiday Inn Express Williamsburg by IHG

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?

8BR Lakefront Lux Retreat: Private Dock, Sleeps 28: This holiday home rental outside of Middlesboro is located on a lake, and has a fireplace, an arcade/games room and a BBQ to put you at ease in your new surroundings. It has 8 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 6 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, Cumberland Gap National Historical Park and Middlesboro Mall 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.