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Choose from 1090 Chestertown Hotel Deals
Comfort Inn & Suites Chestertown
"Problems with checking in and washing machine not working. Staff didn’t care."
Reviewed on Jun 29, 2026
The Lodge at Great Oak Landing
"Is a beautiful and quiet place to relax"
Reviewed on Jun 29, 2026
Red Roof Inn & Suites Chestertown
"The property is a little older and could benefit from a good deep cleaning of carpets and upholstery, but the bed and bathroom were clean and the staff were great. Considering the price of other accomodations in the area it's an excellent value for the money if you're just looking for a clean place ..."
Reviewed on Jun 22, 2026
Historic Inns of Annapolis
"The staff was very friendly. The room was clean."
Reviewed on Jul 2, 2026
Pendry Baltimore
"Loved the hotel ex"
Reviewed on Jun 25, 2026
Best Western Plus Hotel & Conference Center
"Second time we've stayed at this hotel this year. Very nice rooms and very nice staff. The restaurant food and staff are also awesome."
Reviewed on Jun 28, 2026
Hampton Inn Baltimore/Glen Burnie
"Very poor not recommended"
Reviewed on Jun 29, 2026
Annapolis Waterfront Hotel, Autograph Collection
Quality Inn & Suites Bel Air I-95 Exit 77A
"Things were good and clean"
Reviewed on Jun 30, 2026
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
"This place is dump, dirty and smell really bad."
Reviewed on Jul 1, 2026
Best Western Kent Narrows Inn
"The facility is not up to par for the price of the room compared to other hotels across the street. The reception staff were wonderful but when the only elevator broke the manager was rude and unhelpful. Our room was on the top floor and when he was asked about a status update for repairs he said ..."
Reviewed on Jul 1, 2026
The Inn at Chesapeake Bay Beach Club
"The restaurant was wonderful and so was the staff. The grounds were gorgeous and interesting."
Reviewed on Jun 24, 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 1,090 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 1,090 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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