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Middlesboro Holiday Rentals

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Holiday Rentals in Middlesboro

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

Middlesboro
10.0 out of 10, Exceptional, (20)
"Our group had a wonderful time staying at Uncle Ernie's! Everything was neat, tidy, and felt like home. We definitely will be back next time we are in the area!"
United States
Savannah P.
The price is NZ$414
includes taxes & fees
11 Nov - 12 Nov
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,

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 NZ$500
includes taxes & fees
9 Dec - 10 Dec
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

Welcoming 3-bedroom house with AC in charming Middlesboro

Middlesboro
The price is NZ$416
includes taxes & fees
8 Dec - 9 Dec
Welcoming 3-bedroom house with AC in charming Middlesboro

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

Middlesboro
The price is NZ$967
includes taxes & fees
9 Nov - 10 Nov
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU

Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina

Speedwell
9.4 out of 10, Exceptional, (19)
"Excellent private get-away. The property was well stocked with everything you would need to feel at home. I had enough room in the driveway to park my pontoon/pickup truck and an additional 2 vehicles could also park there."
United States
A google U.
The price is NZ$310
includes taxes & fees
6 Dec - 7 Dec
Home in Powell Valley Shores Close to Flat Hollow Marina & Powell Valley Marina

Peaceful & Private! Pet-friendly Williamsburg Home

3.0 star property
Williamsburg
The price is NZ$501
includes taxes & fees
9 Nov - 10 Nov
Peaceful & Private! Pet-friendly Williamsburg Home

Harrogate Hideaway - 5 Min to LMU & Nat'l Park

Harrogate
9.8 out of 10, Exceptional, (7)
"Comfortable space and close to the things/people we visited. Would stay here again"
United States
Scott W.
The price is NZ$344
includes taxes & fees
11 Nov - 12 Nov
Harrogate Hideaway - 5 Min to LMU & Nat'l Park

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 NZ$414
includes taxes & fees
18 Nov - 19 Nov
Beautiful Loft in the Woods

Comfy A-frame cabin with deck, gas grill, Internet, close to marina

2.0 star property
Flat Hollow Marina
10.0 out of 10, Exceptional, (5)
"Perfect for a family getaway on the lake!"
United States
Angel S.
The price is NZ$548
includes taxes & fees
9 Nov - 10 Nov
Comfy A-frame cabin with deck, gas grill, Internet, close to marina

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cumberland Gap
9.2 out of 10, Wonderful, (42)
"Just as advertised. Very quiet and enjoyable stay!"
United States
Anonymous traveller
The price is NZ$379
includes taxes & fees
17 Nov - 18 Nov
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Harrogate Home Mountain View’s Dog Friendly

Harrogate
9.8 out of 10, Exceptional, (20)
"Great location with friendly neighbors!"
United States
Evan C.
The price is NZ$534
includes taxes & fees
9 Nov - 10 Nov
Harrogate Home Mountain View’s Dog Friendly

Charming 3-bedroom house with WiFi, AC in Pineville Kentucky

Pineville
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 NZ$456
includes taxes & fees
10 Nov - 11 Nov
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky

3-story lakefront rustic cabin w/pool table, private hot tub, gas fireplace, A/C

New Tazewell
9.4 out of 10, Exceptional, (29)
"We loved the comfort of the cabin and the view."
United States
Dayneli A.
The price is NZ$1,084
includes taxes & fees
18 Nov - 19 Nov
3-story lakefront rustic cabin w/pool table, private hot tub, gas fireplace, A/C

Lovely dog-friendly cabin overlooking the river w/kids games, Wi-Fi

2.0 star property
New Tazewell
8.6 out of 10, Excellent, (11)
"I’ll lead with the positives - the property was gorgeous, secluded, and a perfect homebase for visiting family nearby. Very pet friendly, clean and modern.The downsides? The neighbors. As you turn onto the street leading to the house you’re greeted by target signs, no trespassing “leave now” “turn around”, “downwind of gun range,” etc. At first, we thought were were lost. It’s overwhelmingly clear that the neighbors do not want you there. Our final night we played “what’s a gunshot,” and “what’s...
United States
kRISTEN h.
The price is NZ$592
includes taxes & fees
9 Nov - 10 Nov
Lovely dog-friendly cabin overlooking the river w/kids games, Wi-Fi

Cozy cabin near Norris Lake with a porch, firepit, gas fireplace & jetted tub

New Tazewell
9.0 out of 10, Wonderful, (9)
"Property was beautiful. Cabin was clean and was a great place for our family to stay. We will be back again! "
United States
Lindsey W.
The price is NZ$848
includes taxes & fees
9 Nov - 10 Nov
Cozy cabin near Norris Lake with a porch, firepit, gas fireplace & jetted tub

Cozy A-frame home with fire pit, deck, pickleball court, and covered boat slip

2.0 star property
Flat Hollow Marina
9.8 out of 10, Exceptional, (8)
"Our family stayed here and loved it. We will be back to stay here!!"
United States
Billy S.
The price is NZ$785
includes taxes & fees
18 Nov - 19 Nov
Cozy A-frame home with fire pit, deck, pickleball court, and covered boat slip

Norris Lake Family Retreat | Lakefront Views + Boat Slip

Speedwell
10.0 out of 10, Exceptional, (1)
"Great location. Easy check in host was easy to communicate with. Had all the amenities that we needed and covered dock was perfect "
United States
Patrick L.
The price is NZ$1,218
includes taxes & fees
12 Nov - 13 Nov
Norris Lake Family Retreat | Lakefront Views + Boat Slip

The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!

Pineville
9.0 out of 10, Wonderful, (2)
"The home was just perfect for what we needed. Looking forward to seeing how it comes out when all construction is finished! Host was very responsive. Will stay again"
United States
Kami L.
The price is NZ$506
includes taxes & fees
9 Dec - 10 Dec
The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!

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

Sharps Chapel
10.0 out of 10, Exceptional, (4)
"Awesome. Breathtaking view"
United States
Auston C.
The price is NZ$547
includes taxes & fees
20 Nov - 21 Nov
Serenity Villa: Luxurious Retreat with Hot Tub, Rooftop Deck & Mountain View's

Dog-friendly lake home with private floating dock - jetted tub, firepit, & decks

New Tazewell
7.8 out of 10, Good, (18)
"Just what we were looking for. "
United States
Michael Jr. N.
The price is NZ$790
includes taxes & fees
9 Nov - 10 Nov
Dog-friendly lake home with private floating dock - jetted tub, firepit, & decks
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

Find out more about Middlesboro

Everything you need to know about Middlesboro holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middlesboro holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middlesboro holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Middlesboro holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middlesboro. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middlesboro holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlesboro holiday rentals we have selected for you start as low as NZ$1,465 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middlesboro rentals

At Expedia, we put the best Middlesboro holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Middlesboro rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middlesboro holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middlesboro. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Family Affair, room 4 30, 15 Beds, 2 FULL Kitchens!!! Huge dock w 2 boat slips: This holiday home rental outside of Middlesboro is located on a lake, and has a fireplace, a balcony 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. Kick off your shoes and enjoy yourself with a selection of games and 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 Country Club 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.