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
31 Jul - 2 Aug
In two months
11 Sep - 13 Sep
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Middlesboro vacation rentals

Desk, iron/ironing board, WiFi, bed sheets

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, (6 reviews)
"We enjoyed our stay. "
United States
Emily S.
The price is SAR 645
SAR 1,332 total
includes taxes & fees
14 Jul - 15 Jul
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Exterior

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 1,298 total
includes taxes & fees
28 Jul - 29 Jul
Welcoming 3-bedroom house with AC in charming Middlesboro
Dining

Private bungalow close to LMU, ARH, Cumberland Gap

Private bungalow close to LMU, ARH, Cumberland Gap
Middlesboro
The price is SAR 588
SAR 1,267 total
includes taxes & fees
14 Jul - 15 Jul
Private bungalow close to LMU, ARH, Cumberland Gap
Fridge, microwave, oven, stovetop

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 681
SAR 1,430 total
includes taxes & fees
11 Aug - 12 Aug
House close to ARH Hospital, Tackett Creek & LMU!
1 bedroom, WiFi, bed sheets

Modern 20’ Travel Trailer with bunks and a queen bed

Modern 20’ Travel Trailer with bunks and a queen bed
Speedwell
The price is SAR 289
SAR 522 total
includes taxes & fees
20 Jul - 21 Jul
Modern 20’ Travel Trailer with bunks and a queen bed
Property grounds

The Nomad on Norris Lake

The Nomad on Norris Lake
New Tazewell
The price is SAR 845
SAR 1,418 total
includes taxes & fees
10 Aug - 11 Aug
The Nomad on Norris Lake
Property grounds

Wake&Lake at Norris Landing Marina-Waterfront RV Retreat with Deck + Slip Option

Wake&Lake at Norris Landing Marina-Waterfront RV Retreat with Deck + Slip Option
Tazewell
10.0 out of 10, Exceptional, (1 review)
"Everything was exceptional! The hosts are very accommodating and the camper has everything you would need to make your stay comfortable!"
United States
Morgan H.
The price is SAR 563
SAR 715 total
includes taxes & fees
14 Jul - 15 Jul
Wake&Lake at Norris Landing Marina-Waterfront RV Retreat with Deck + Slip Option
Interior

One Bedroom Rustic Cabin

One Bedroom Rustic Cabin
Speedwell
The price is SAR 184
SAR 366 total
includes taxes & fees
14 Jul - 15 Jul
One Bedroom Rustic Cabin
1 bedroom, free WiFi, bed sheets

Quaint Studio APT Near ATV Trails & Norris Lake

Quaint Studio APT Near ATV Trails & Norris Lake
LaFollette
9.6 out of 10, Exceptional, (11 reviews)
"Check in was very easy amazing little place. Loved the mornings going out to the porch and hearing the birds chirping. Definitely coming back and staying again "
United States
Melisza
The price is SAR 199
SAR 513 total
includes taxes & fees
14 Jul - 15 Jul
Quaint Studio APT Near ATV Trails & Norris Lake
Property grounds

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, (8 reviews)
"clean house very beautiful, host was amazing, scenery stunning. "
United States
Evelyn B.
The price is SAR 598
SAR 1,094 total
includes taxes & fees
11 Aug - 12 Aug
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Terrace/patio

Peaceful & Private! Pet-Friendly Williamsburg Home

Peaceful & Private! Pet-Friendly Williamsburg Home
Williamsburg
10.0 out of 10, Exceptional, (3 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 1,167 total
includes taxes & fees
26 Jul - 27 Jul
Peaceful & Private! Pet-Friendly Williamsburg Home
Fridge, microwave, oven, stovetop

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, (16 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 436
SAR 800 total
includes taxes & fees
14 Jul - 15 Jul
Harrogate Hideaway - 5 Min to LMU & Nat`l Park
Exterior

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, (48 reviews)
"Cozy place perfect for what we needed. "
United States
Emily N.
The price is SAR 454
SAR 902 total
includes taxes & fees
15 Jul - 16 Jul
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Fridge, microwave, oven, stovetop

Remodeled Western Country Getaway Near Lake & Trails

Remodeled Western Country Getaway Near Lake & Trails
LaFollette
10.0 out of 10, Exceptional, (2 reviews)
"Very clean and nice apartment. Just as advertised. Had everything we needed and we were very pleased. Great place! You will not be disappointed. We will definitely be going back!"
United States
Gregory T.
The price is SAR 297
SAR 701 total
includes taxes & fees
14 Jul - 15 Jul
Remodeled Western Country Getaway Near Lake & Trails
Terrace/patio

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, (11 reviews)
"The hosts were wonderful, very accommodating and helpful through our stay. The cabin was clean and nicely put together for a relaxing visit."
United States
Sharon W.
The price is SAR 398
SAR 690 total
includes taxes & fees
14 Jul - 15 Jul
Peaceful cabin with AC in charming Tazewell. Welcome to relaxation!
House (2 Bedrooms) | Front of property

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
14 Jul - 15 Jul
Peaceful & Private! Pet-friendly Williamsburg Home
Interior

Beautiful Mountain View surrounded by lakes with fishing ,boating, and hiking

Beautiful Mountain View surrounded by lakes with fishing ,boating, and hiking
Tazewell
The price is SAR 233
SAR 505 total
includes taxes & fees
17 Jul - 18 Jul
Beautiful Mountain View surrounded by lakes with fishing ,boating, and hiking
Interior

Calm Country Oasis - Creek, ATV Trls & Norris Lake

Calm Country Oasis - Creek, ATV Trls & Norris Lake
Speedwell
9.6 out of 10, Exceptional, (24 reviews)
"Clean home, responsive host, beautiful location, family friendly."
United States
Anna S.
The price is SAR 567
SAR 1,181 total
includes taxes & fees
12 Aug - 13 Aug
Calm Country Oasis - Creek, ATV Trls & Norris Lake
Exterior

Blissful Bungalow across from LMU campus

Blissful Bungalow across from LMU campus
Harrogate
9.6 out of 10, Exceptional, (39 reviews)
"Very convenient to everything we needed to do, very clean and neat"
United States
Brandi L.
The price is SAR 522
SAR 963 total
includes taxes & fees
11 Aug - 12 Aug
Blissful Bungalow across from LMU campus
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
Speedwell
9.2 out of 10, Wonderful, (23 reviews)
"Nice place. Everything you need and more"
United States
Jeff L.
The price is SAR 338
SAR 676 total
includes taxes & fees
14 Jul - 15 Jul
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina
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

Lake Front 2-Bedroom Home W/ Privacy! Beautiful Views & Numerous Amenities...

Lake Front 2-Bedroom Home W/ Privacy! Beautiful Views & Numerous Amenities...

10/10 Excellent
"Very beautiful lake house with a sliver of lake to gaze at from the big back deck with plenty of seating. Two nice bedrooms sized bedrooms with a bathroom for each. Great kitchen and plenty of seating in the living room. Good, easy communication with the owner. Would stay there again."
jeff 7-night trip
Posted 17 hours ago
Lake Front 2-Bedroom Home W/ Privacy! Beautiful Views & Numerous Amenities...

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?

Lake Front 2-Bedroom Home W/ Privacy! Beautiful Views & Numerous Amenities...: This vacation home rental near Middlesboro is located on a lake and has a patio, a private yard, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

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, Cumberland Gap National Historical Park and Middlesboro Country Club 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.