Hotels in Chesapeake Bay

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Where to stay in Chesapeake Bay?

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Learn more about Chesapeake Bay

Cruise the bay's tranquil waters, spotting ospreys and exploring charming waterfront towns like St. Michaels. Feast on succulent blue crabs and fresh oysters at local seafood shacks dotting the shoreline.

USS Wisconsin BB-64 featuring a marina

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Frequently asked questions

Can I book refundable accommodations in Chesapeake Bay?
If you need the flexibility to change your plans to Chesapeake Bay, most properties provide refundable* rates you can book. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Chesapeake Bay if I want a vacation home instead of a hotel?
If you're looking for a good alternative to a hotel, browse our selection of 4166 vacation homes. In addition, there are 2017 apartments and 1262 condos.
Why should I book my Chesapeake Bay hotel with Hotels.com?
There are lots of reasons to book your Chesapeake Bay trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.