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Choose from 1101 Chestertown Hotel Deals
Red Roof Inn & Suites Chestertown
"Perfectly adequate room for a visit to Chestertown. Good furnishings and amenities. Walkable to stores and restaurants."
Reviewed on Sep 23, 2026
The Lodge at Great Oak Landing
"Unique location with a beachy feel. Comfortable with basic amenities. Communication with the lodge staff was very good as I checked in late and they sent me my room entry information. I would stay there again."
Reviewed on Sep 21, 2026
Comfort Inn & Suites Chestertown
Historic Inns of Annapolis
"Location is excellent. Parking is tough, but valet parking is a good deal. The sheets were only so-so, and the “windows” looked out onto the ballroom with some limited natural light from the ballroom skylights. They leave the ballroom twinkle lights on all night, so the room darkening shades are ..."
Reviewed on Sep 24, 2026
Pendry Baltimore
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Best Western Plus Hotel & Conference Center
"It was great"
Reviewed on Sep 23, 2026
Hampton Inn Baltimore/White Marsh
Annapolis Waterfront Hotel, Autograph Collection
"The view from our room was incredible. The property is clean and the beds comfortable. For the price, however, the only thing that justifies it is the view and location. There are 2 restaurants- Marmo was disappointing and overpriced. The cantina was great. Unfortunately, they take up all of the ..."
Reviewed on Sep 22, 2026
Hampton Inn & Suites Edgewood/Aberdeen-South
Hilton Garden Inn Baltimore/White Marsh
Quality Inn & Suites Bel Air I-95 Exit 77A
"Stayed here before and service is still superb"
Reviewed on Sep 23, 2026
Find cheap hotels in Chestertown
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Choosing the right hotel in Maryland has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Chestertown’s 1,101 hotels. Choose the one that best catches your trip’s tourist drift.
If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $69. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Chestertown hotel deals at the last minute.
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Frequently Asked Questions About Chestertown hotels
Where can I find the best last-minute travel deals?
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How many hotels are there in Chestertown?
With over 1,101 hotels in Chestertown, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $69.
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