Top Red Roof Inn in Chestertown, MD from $59

An aerial view of a town with a river, buildings, and surrounding greenery.

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Our top choices for Chestertown Red Roof Inn

A living room with a fireplace, a television, and a stone accent wall.

1. Red Roof Inn & Suites Chestertown

Chestertown

Mary

$72 nightly

Nov 3 - Nov 4

Total with taxes and fees

A hotel lobby with seating areas, a kitchenette, and a large window offering a view.

2. Red Roof Inn Baltimore South - Glen Burnie

Ferndale

Dewey

$85 nightly

Nov 1 - Nov 2

Total with taxes and fees

A hotel room with a bed, a desk, a chair, a television, and a mirror.

3. Red Roof Inn Aberdeen

Aberdeen

Mark

$53 nightly

Nov 1 - Nov 2

Total with taxes and fees

A hotel room with a bed, a desk, a chair, and a television.

4. Red Roof Inn Edgewood

Edgewood

Jailine

$71 nightly

Nov 1 - Nov 2

Total with taxes and fees

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Top Chestertown Hotel Reviews

Country Inn & Suites by Radisson, Baltimore North, MD

8/10 Good

"I specifically chose this hotel because they had a hot tub and they were close to a physically demanding job that I was doing 2 days in a row. I had hoped to get some relaxation and relief but the hot tub was broken. The pool was relaxing enough but it seemed like it was ready for a good cleaning as was the area around the pool deck. There were no lights on when I arrived at the pool so I had to go to the front desk and the clerk attended to the issue quickly and walked down to the pool area and turned lights on for me. Most of the common areas were clean enough but some areas (like around the ice machines and where the vending machines used to be) were pretty grubby and nasty. One set of blinds was so broken and filthy that they should have just removed them completely for some improvement. The room was clean but a bit dated. There was shampoo, conditioner, liquid body soap and body lotion available if I had wanted them. There were also 2 small bars of soap for the sink area. The towels were clean and there were 2 sets in the room (I used both for one overnight stay as the bath towels were on the small side). The bed was comfortable enough but the plush armchair was so old and filthy I couldn't bring myself to sit on it but the desk chair did nicely. The breakfast was almost edible but I would plan on sticking to the fresh fruit and packaged yogurt. Overall it was decent enough that I would stay here again for a quick overnight between work days."