Find cottages near Chesapeake Bay

We found 283 cottages — enter your dates for availability
If you'd like to stay close to Chesapeake Bay, take a look at holiday rentals to choose your home away from home. Whether you’re staying in a holiday home with family or friends, you'll find the amenities that you need and want, which might include air conditioning and a pool. At the end of the day, you're sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

Explore Chesapeake Bay cottage rentals

Image of Smith Beach cottage w/ private sunset
Premier Host

Smith Beach cottage w/ private sunset

Sleeps 4 · 2 bedrooms · 1 bathroom
9.2 out of 10
wonderful
(26 reviews)
More information about Smith Beach cottage w/ private sunset, opens in a new tab

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  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently Asked Questions

Are there any cottage rentals in Chesapeake Bay?

Choose from 458 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.

How much does it cost to stay in a cottage rental in Chesapeake Bay?

Fancy or basic, in a tourist hot spot or a little further 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 holiday rentals offer discounts for extended stays, so keep your eyes peeled for special offers.

When is the best time to rent a cottage in Chesapeake Bay?

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

Where can I rent a Chesapeake Bay holiday cottage with great views?

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 Bookabach.

Does Chesapeake Bay have any lakeside cottages?

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

What are the top things to do in Chesapeake Bay?

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.

Why should I book my holiday cottage with Bookabach?

When you stay in a Bookabach cottage rental, the only people you'll share your living space with are whoever you take with you. It will just be you, your nearest and dearest and the whole property to yourselves. Our flexible cancellation policies also mean you can book your cottage with confidence should your plans change.