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Middlesboro Holiday Rentals

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Check prices for these dates

Tonight
2 Aug - 3 Aug
Tomorrow
3 Aug - 4 Aug
Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug

Holiday Rentals in Middlesboro

Cozy floating home, AC on Norris Lake at Straight Creek Marina
Interior

Cozy floating home, AC on Norris Lake at Straight Creek Marina

10.0 out of 10, Exceptional, (1)
"Would definitely stay at Derrick’s floating cabin again, great location and hospitality! "
Cozy floating home, AC on Norris Lake at Straight Creek Marina
Fabulous view, walking distance from Flat Hollow Marina
Property grounds

Fabulous view, walking distance from Flat Hollow Marina

9.6 out of 10, Exceptional, (14)
"Perfect for all our needs, clean, close to the marina."
Fabulous view, walking distance from Flat Hollow Marina
Dog-friendly waterfront home with a firepit, grill, deck, board games, & dock
Fridge, microwave, oven, stovetop

Dog-friendly waterfront home with a firepit, grill, deck, board games, & dock

8.0 out of 10, Very good, (16)
"We really liked the location of this home and the views were beautiful! There were plenty of amenities to meet our needs."
Dog-friendly waterfront home with a firepit, grill, deck, board games, & dock
Lakefront home at Tumbling Run Estates w/ Kayaks
Fridge, microwave, oven, stovetop

Lakefront home at Tumbling Run Estates w/ Kayaks

9.8 out of 10, Exceptional, (17)
"Awesome house and location Gorgeous, convenient and lots of fun for all ages and big family.gatherings. We also rented a pontoon and it was great too! Planning our next trip! Highly recommend."
Lakefront home at Tumbling Run Estates w/ Kayaks
9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock
Smart TV, fireplace, DVD player, table football

9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock

9.8 out of 10, Exceptional, (104)
"We went to ride the trails and enjoy the lake life. It was an awesome place. "
9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock
LakeFront 7 bedroom Cottage. Private Cove, no Steps to Water, golf cart!
Exterior

LakeFront 7 bedroom Cottage. Private Cove, no Steps to Water, golf cart!

10.0 out of 10, Exceptional, (29)
"Enjoyed the view and the property"
LakeFront 7 bedroom Cottage. Private Cove, no Steps to Water, golf cart!
Calm Country Oasis - Creek, ATV Trls & Norris Lake
Property grounds

Calm Country Oasis - Creek, ATV Trls & Norris Lake

9.4 out of 10, Exceptional, (19)
"We had a wonderful weekend:)"
The price is HK$1,154
HK$2,434 total
includes taxes & fees
19 Aug - 20 Aug
Calm Country Oasis - Creek, ATV Trls & Norris Lake
Beautiful lakefront house with full kitchen, private dock, & hot tub
Terrace/patio

Beautiful lakefront house with full kitchen, private dock, & hot tub

9.8 out of 10, Exceptional, (86)
"Words can’t describe how amazing this place was. We didn’t want to leave! We will 100% be staying here again. "
Beautiful lakefront house with full kitchen, private dock, & hot tub
9 bdrm covered dock, firepit and large bar on water, Baltic hot tub, sleeps 26,
Terrace/patio

9 bdrm covered dock, firepit and large bar on water, Baltic hot tub, sleeps 26,

10.0 out of 10, Exceptional, (3)
"Awesome house!"
9 bdrm covered dock, firepit and large bar on water, Baltic hot tub, sleeps 26,
Spring Lily Retreat - Spacious, Lakefront, Hot Tub, Private Dock, Peaceful Cove!
Fridge, microwave, oven, stovetop

Spring Lily Retreat - Spacious, Lakefront, Hot Tub, Private Dock, Peaceful Cove!

9.8 out of 10, Exceptional, (64)
"GREAT PLACE - PARKING IS A LITTLE HARD"
Spring Lily Retreat - Spacious, Lakefront, Hot Tub, Private Dock, Peaceful Cove!
Lakefront Sharps Chapel Retreat w/ Boat Dock!
Property grounds

Lakefront Sharps Chapel Retreat w/ Boat Dock!

6.4 out of 10, (6)
"Wonderful lakehouse! Well stocked kitchen, comfortable beds and very clean. We enjoyed our stay here!"
Lakefront Sharps Chapel Retreat w/ Boat Dock!
Tan Lines & Good Times-Brand new 6 bed/ 8 bath-Water Front,Private Dock, Hot tub
Interior

Tan Lines & Good Times-Brand new 6 bed/ 8 bath-Water Front,Private Dock, Hot tub

2.0 star property
10.0 out of 10, Exceptional, (2)
"New home, comfortable beds, well stocked, easy lake access. Amazing bunk room for the big kids. Beautiful!"
Tan Lines & Good Times-Brand new 6 bed/ 8 bath-Water Front,Private Dock, Hot tub
Waker's Paradise: Lakefront,9br/8.5ba, Private Dock,Hot Tub,Gameroom,Sleeps 32
Interior

Waker's Paradise: Lakefront,9br/8.5ba, Private Dock,Hot Tub,Gameroom,Sleeps 32

9.8 out of 10, Exceptional, (47)
"Great experience- accurate listing that ensured space for all!"
Waker's Paradise: Lakefront,9br/8.5ba, Private Dock,Hot Tub,Gameroom,Sleeps 32
Cabin on water with Covered Boat Dock -Gentle Slope to Lake!
Terrace/patio

Cabin on water with Covered Boat Dock -Gentle Slope to Lake!

10.0 out of 10, Exceptional, (31)
"Great location, clean house, met all our needs! Hosts were always very responsive and made sure we had a great stay. We will be back!"
Cabin on water with Covered Boat Dock -Gentle Slope to Lake!
Lakefront House at Summer Breeze w/ Private Dock w/ Kayaks
Terrace/patio

Lakefront House at Summer Breeze w/ Private Dock w/ Kayaks

10.0 out of 10, Exceptional, (21)
"Host was amazing with their information and house had everything we needed!"
Lakefront House at Summer Breeze w/ Private Dock w/ Kayaks
Book your fall retreat today!
Property grounds

Book your fall retreat today!

10.0 out of 10, Exceptional, (45)
"So perfect place"
Book your fall retreat today!
Lakeside Lodge- Dock, Hot Tub, Fire Pit+ 8 Kayaks
Smart TV, fireplace, video games, DVD player

Lakeside Lodge- Dock, Hot Tub, Fire Pit+ 8 Kayaks

9.6 out of 10, Exceptional, (47)
"Very spacious and fun house with tons to do!"
Lakeside Lodge- Dock, Hot Tub, Fire Pit+ 8 Kayaks
Treasure Cove, Waterfront, 9 Bed/9 Bath, Double Decker Dock, arcade games
Property grounds

Treasure Cove, Waterfront, 9 Bed/9 Bath, Double Decker Dock, arcade games

9.8 out of 10, Exceptional, (45)
"Loved the lake and the view."
Treasure Cove, Waterfront, 9 Bed/9 Bath, Double Decker Dock, arcade games
Be the family hero - The Great Escape is Waterfrnt, 9 bdrms, with water slide
Outdoor dining

Be the family hero - The Great Escape is Waterfrnt, 9 bdrms, with water slide

9.8 out of 10, Exceptional, (73)
"We had a wonderful time. The place had everything we needed, was clean, and provided the perfect setting for our family vacation. "
Be the family hero - The Great Escape is Waterfrnt, 9 bdrms, with water slide
LAKE DAZE--Lakefront/No Wake/9br/12ba/Private Dock/Hot Tub/Sleeps 32
Fridge, microwave, oven, stovetop

LAKE DAZE--Lakefront/No Wake/9br/12ba/Private Dock/Hot Tub/Sleeps 32

9.6 out of 10, Exceptional, (65)
"Love the place super relaxing "
LAKE DAZE--Lakefront/No Wake/9br/12ba/Private Dock/Hot Tub/Sleeps 32
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 Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG

10/10 Excellent
"Bed was amazingly comfortable..continental breakfast with great options.. staff very friendly and helpful."
Sandy 2-night trip
Posted 3 days ago
Holiday Inn Express Middlesboro by IHG

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?

9/9 Lakefront/Mountains/Woods - Protected Cove - Private Dock: 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 9 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals are there in Middlesboro?

With 4 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?

Cumberland Gap National Historical Park and Kentucky Ridge State Forest are a couple of scenic spots to enjoy the outdoors, whereas Bell County Historical Society Museum is one of the cultural attractions. 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.