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Choose from 1086 Chestertown Hotel Deals
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
"They could serve the breakfast and charge a little more, have a functional gym, have clean carpet in the room or hallway. Some are old!"
Reviewed on Jul 22, 2026
The Lodge at Great Oak Landing
"The room seemed very old, but OK generally. It looked out on a very unattractive storage area. Staff leaves at 4:30 and I got there a little later so the woman had to go back inside and get my information (which she said was already on my room door though I didn't see that). This is an old hotel ..."
Reviewed on Jul 20, 2026
Historic Inns of Annapolis
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Pendry Baltimore
Hampton Inn Baltimore/Glen Burnie
"Clean room but not everyday?"
Reviewed on Jul 21, 2026
Annapolis Waterfront Hotel, Autograph Collection
"It was an amazing stay for us and definitely will be back."
Reviewed on Jul 22, 2026
Quality Inn & Suites Bel Air I-95 Exit 77A
Best Western Plus Hotel & Conference Center
Best Western Kent Narrows Inn
"It's a decent place to stay except for the noise from the Kent Narrows Bridge. Get a room on the front of the hotel to avoid it"
Reviewed on Jul 21, 2026
Hilton Garden Inn Kent Island Marina
"Nice stay!"
Reviewed on Jul 21, 2026
Find cheap hotels in Chestertown
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For you, intrepid voyager, Hotwire has a large selection of the best hotels in Chestertown.
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 1,086 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 $70. 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.
While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Chestertown. No matter your reason for visiting Chestertown, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.
Frequently Asked Questions About Chestertown hotels
Where can I find the best last-minute travel deals?
If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can unlock great deals on your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Chestertown for as low as $70.
How many hotels are there in Chestertown?
With over 1,086 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 $70.
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