Middlesboro, KY Cottages from AED 640

An aerial view of a town surrounded by mountains, with a mix of residential and commercial buildings, and a highway running through the center.

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Our top choices for Middlesboro cottages

A single-story house with a porch, a mailbox, and a small garden.

1. Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cumberland Gap

JOHN H.

AED 747 total

includes taxes & fees

19 Nov - 20 Nov

A covered outdoor deck with wooden flooring and metal chairs.

2. Peaceful & Private! Pet-friendly Williamsburg Home

Williamsburg

AED 1,129 total

includes taxes & fees

7 Nov - 8 Nov

A single-story house with a front porch, a large window, and a well-maintained lawn.

3. Calm Country Oasis - Creek, ATV Trls & Norris Lake

Speedwell

Sandra

AED 920 total

includes taxes & fees

8 Nov - 9 Nov

4. Robertson Ridge Hideaway Cottage

Hinkle

Isaac L.

AED 640 total

includes taxes & fees

6 Dec - 7 Dec

A two-story wooden cabin with a balcony, a covered porch, and a solar panel on the roof.

5. Peaceful Mountain Cabin w/ Views in Williamsburg

Williamsburg

Chandler

AED 1,253 total

includes taxes & fees

7 Nov - 8 Nov

A rural landscape with a small wooden house, a gravel path, and a forested hill in the background.

6. Studio 8 Mi to Norris Lake! Couples & Pets Welcome

Tazewell

AED 898 total

includes taxes & fees

7 Nov - 8 Nov

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Top Middlesboro Hotel Reviews

Pine Mountain State Resort Park

8/10 Good

"The room was very clean, the staff was very friendly and helpful, the breakfast was very good, and the balcony was neatly arranged."

Sleep Inn & Suites Middlesboro

8/10 Good

"The best thing about this hotel is the location. It sits by itself up on a hill with trees all around; away from the highway, very scenic and quiet. Nice artwork, lots of room space with separate sitting area. Clean, comfortable. There was some mold in the shower. The door handle malfunctioned so it was hard to open the door every time with the key card. No freezer in the refrigerator. The worst thing was there were no teabags for 2 days at the breakfast. As a tea drinker, I don't want anything special, just a black/orange pekoe blended tea, any brand, store brand will do. I don't want herbal or decaffeinated tea in the morning. So often tea drinkers are discriminated against. Can you imagine if they had no coffee 2 days in a row?? Teabags are not perishable, so there is no reason to ever run out!"

Econo Lodge Middlesboro

10/10 Excellent

"Soon as we arrived, we were met by Susan who worked inside. ..so friendly ,helpful ,..such a warm welcoming and that’s the beginning of an awesome stay ..we made coffeees (delicious) and she gave us some snacks ..room was awesome and clean as a whistle ..breakfast was delicious ..just go you won’t be disappointed..Susan thanks for the directions to the mountain it was breathtaking .."

Holiday Inn Express Williamsburg by IHG

8/10 Good

"The location of this property is very good and easy to access. Room was spacious and well-equipped except for a coffee maker. Our room happened to be just above the roof top for the front entrance leaving an unattractive view. Also, the darker shade on the window would not close leaving the room well-lit all night from bright lights outside. And cars turning at an intersection not far away had their headlights aimed directly at the window, which was a little annoying. The best part of our stay was the breakfast. It provided a very good variety and was being added to frequently."

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

10/10 Excellent

"It was a very nice and beautiful place. We rented it because we got married on Saturday and we need a place for the family to stay and believe it or not. This once belonged to one of my really good friends. This place did back years ago"

Book your fall retreat today!!! Lake all day and fire at night.

10/10 Excellent

"Large family (19 people) vacation was wonderful, plenty of space for all the ages in our group. Spaces for everyone in the house for quiet time or gathering. House came with more than enough kitchen supplies to create meals for our group , games, puzzles, ping pong, cornhole. The walk to the dock was the only troublesome thing,one of our family members was not able to walk it, everyone else managed to the dock swam, kayaked, played on floating mat, fished, had an enjoyable experience. Luckily for October weather was fabulous only 1 rainy day and was warm enough temps and lake temp to swim. Definitely would recommend this home. Owner was easy to contact and answered promptly."

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Middlesboro cottages

1. Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

2. Peaceful & Private! Pet-friendly Williamsburg Home

3. Calm Country Oasis - Creek, ATV Trls & Norris Lake

4. Robertson Ridge Hideaway Cottage

5. Peaceful Mountain Cabin w/ Views in Williamsburg

6. Studio 8 Mi to Norris Lake! Couples & Pets Welcome

Find vacation rentals that suit your style

Top Middlesboro Hotel Reviews

Pine Mountain State Resort Park

Sleep Inn & Suites Middlesboro

Econo Lodge Middlesboro

Suburban Studios Middlesboro

Imperial Inn Tazewell

Holiday Inn Express Williamsburg by IHG

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

Book your fall retreat today!!! Lake all day and fire at night.

Beautiful Lakefront Getaway - Sleeps 26 - Norris Lake’s Best Location

Frequently asked questions

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Search Cottages in Middlesboro

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Middlesboro cottages

1. Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

2. Peaceful & Private! Pet-friendly Williamsburg Home

3. Calm Country Oasis - Creek, ATV Trls & Norris Lake

4. Robertson Ridge Hideaway Cottage

5. Peaceful Mountain Cabin w/ Views in Williamsburg

6. Studio 8 Mi to Norris Lake! Couples & Pets Welcome

Find vacation rentals that suit your style

Top Middlesboro Hotel Reviews

Pine Mountain State Resort Park

Frequently asked questions

Explore a world of travel with Expedia