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Driftwood Inn
609 Washington Avenue, Chestertown, MD, United States
The Lodge at Great Oak Landing
Chestertown, MD, United States
Red Roof Inn & Suites Chestertown
160 Scheeler Road, Chestertown, MD, United States
Carriage House Hideaway In Center of Chestertown
Chestertown, MD, United States
Comfort Inn and Suites Chestertown
150 Scheeler Road, Chestertown, MD, United States
First Floor Studio Apartment in Historic Chestertown
Chestertown, MD, United States
Comfort Inn and Suites Chestertown
150 Scheeler Road, Chestertown, MD, United States
Driftwood Inn
609 Washington Avenue, Chestertown, MD, United States
Red Roof Inn & Suites Chestertown
160 Scheeler Road, Chestertown, MD, United States
Contemporary waterfront house with private dock & kayaks!
Chestertown, MD, United States
Carriage House Hideaway In Center of Chestertown
Chestertown, MD, United States
Lowest Hotel Price | R1 236 |
|---|---|
Most Popular Hotel (5-star) | Brampton 1860 |
Hotels Near Airport | 2475 |
Hotels in Chestertown, MD show a range of prices for their rooms. These are determined by factors such as availability, locale and amenities. On average, rooms will be around R2 342 per night.
The cheapest month to book a hotel in Chestertown, MD is January. The cost of your room could be as much as 41% cheaper than in peak months.
Hotel rooms in Chestertown, MD are generally cheapest on Tuesday and more costly on Wednesday.
The average temperature in Chestertown during August is around 75,2 °F which makes it the perfect time to spend time having fun and seeing something new outside at popular area attractions.
The number of operators available for hotels in Chestertown is 55 as of July 2025.
Prices for hotels in Chestertown were last updated today.
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