Top Red Roof Inn in Chestertown, MD - Expedia

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 multi-story brick building with a covered entrance and a parking lot.

A hotel sign with a red background and white lettering, a parking lot, and a building with a brick facade.

A spacious living room with a fireplace, a stone accent wall, and a television mounted above it.

A hotel room with a bed, a sofa, a desk, and a painting on the wall.

1. Red Roof Inn & Suites Chestertown

Chestertown

United States

Linda

$72 nightly

$80 total

Oct 6 - Oct 7

Total with taxes and fees

A Red Roof Inn sign on a brick wall with two leather chairs and a small table.

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

A Red Roof Inn reception area with a stone wall backdrop, two leather chairs, a wooden stool, a flat-screen TV, and artwork on the wall.

A coffee station with a coffee maker, sugar, creamer, and a hot water dispenser.

2. Red Roof Inn Aberdeen

Aberdeen

United States

Seth

$60 nightly

$67 total

Oct 1 - Oct 2

Total with taxes and fees

A Red Roof Inn with a brick building, a covered walkway, and a landscaped area with trees and flowers.

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

A kitchenette with a black refrigerator and a microwave.

Two vending machines against a brick wall, one with snacks and the other with beverages.

3. Red Roof Inn Edgewood

Edgewood

United States

Jailine

$69 nightly

$78 total

Oct 12 - Oct 13

Total with taxes and fees

A hotel room with a large bed, a desk, a television, and a curtain.

A swimming pool with sun loungers and umbrellas, surrounded by a fence, with a parking lot in the background.

A Red Roof Inn with a white van parked under the building's awning.

A fitness center with various exercise machines, including treadmills, an elliptical, and a stationary bike.

4. Red Roof Inn Baltimore South - Glen Burnie

Ferndale

Australia

Rob

$85 nightly

$96 total

Oct 4 - Oct 5

Total with taxes and fees

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Top Chestertown Hotel Reviews

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent

"Beautiful inn. Upscale, beds and room space very comfortable, clean, newly decorated. Grounds are lovely with cozy spaces outdoors to comfortably sit at a firepit or walk through the chefs garden its a place to relax, gather with friends, or simply enjoy."

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"Excellent location. Marriott has renovated the bar downstairs; one side is a Mexican restaurant and the other is Italian. Both have great food and service."

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent

"Nice room. Nice stay."

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

10/10 Excellent

"This is a wonderful facility for a couple or family. The restaurant is just "ok"."

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

10/10 Excellent

"Perfectly adequate room for a visit to Chestertown. Good furnishings and amenities. Walkable to stores and restaurants."

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