Chesapeake Bay cottage rentals

We found 496 cottage rentals — enter your dates for availability

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    Our Book with Confidence Guarantee gives you 24/7 support
  • 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 496 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 Stayz 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 Stayz.
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 Stayz’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 Stayz?
When you stay in a Stayz 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.

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