Chesapeake Bay Hotels

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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.
Showing deals for:18 Jul - 20 Jul

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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 which includes a marina

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Frequently asked questions

Can I book a refundable accommodation option in Chesapeake Bay?
If you want the flexibility to change your plans to Chesapeake Bay, most hotels offer refundable* rates that you can book. You can find this accommodation 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 holiday rental instead of a hotel?
If you want a good alternative to a hotel, look over our selection of 4166 holiday 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, our Price Guarantee ensures that you always get the lowest price, and you can earn rewards on every booking.