Chesapeake Bay cottage rentals

Choose from 499 cottage rentals in Chesapeake Bay. Take your loved ones on an adventure to Virginia Beach or tour other exciting cities like Garrett County and McHenry. Wherever you plan to go, our cottages provide the opportunity to switch off the phone and enjoy a relaxing retreat without unwelcome distractions.

Fancy or basic, in a tourist hot spot or a little farther out, high season or shoulder season — these factors and more will determine how much your cottage rental in Chesapeake Bay will cost. The length of your stay can also affect the final price. Some vacation rentals offer discounts for extended stays, so keep your eyes peeled for special offers.

March is when most Vrbo guests book a cottage rental in Chesapeake Bay. You can expect average temperatures of between 39ºF (4ºC) and 51ºF (11ºC) if you plan your trip during this time of year.

Book a cottage rental in Chesapeake Bay that offers views of historic areas or other lovely scenery just beyond your door. Privacy, comfort and stunning vistas? Find a property that comes with it all on Vrbo.

Lovely views of shimmering water, the wonder of nature and outdoor activities are just a few of the things to enjoy in one of Vrbo’s lakeside cottage rentals. Use our “Location” filter and check the “Lake” box to see if there are any cozy retreats in Chesapeake Bay by the water.

Venture out and experience everything Chesapeake Bay has to offer from the comfort of your cottage rental. We recommend doing a bit of research on what you’d like to see and do, so you can plan the perfect trip.

When you select a Vrbo cottage rental, the only people you have to share your space with are whoever you bring with you. It’s just you, family or friends and the entire place for your exclusive use. And when you sign up to our free loyalty program, One Key™, you can earn OneKeyCash™* on eligible bookings on Vrbo, Hotels.com and Expedia. What’s more, our flexible cancellation policies also mean you can book your cottage with confidence in case your plans change. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Vrbo, Expedia and Hotels.com.