Find beach rentals near Chesapeake Bay

We found 962 beach rentals — enter your dates for availability

Find spaces that suit your style

  • Peace of mind

    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

How much does it cost to stay in a beach holiday rental in Chesapeake Bay?
If you're planning to stick around a while and want to save on your beach holiday rental, use our "Discounts" filter. This will show you any properties in Chesapeake Bay that offer deals for longer stays, such as a weekly or monthly discount. You can also fine-tune your search by entering your maximum spend per night. While several factors will influence how much you pay, we'll help you score a seaside getaway at a price that's perfect for you.
When is the best time to book a beach holiday rental in Chesapeake Bay?
March is when the majority of guests book a beach holiday rental in Chesapeake Bay. You can expect average temperatures of between 4ºC and 11ºC if you plan your coastal getaway at this time of year.
Where can I book a Chesapeake Bay beach holiday rental with great views?
Book your beach holiday rental in Chesapeake Bay that boasts views of historic areas or other lovely scenery to wake up every morning to. Comfort, privacy and vistas to remember? Find a house that has everything you need for the perfect seaside getaway on Bookabach.
What are the most popular beaches in Chesapeake Bay?
Ocean City Beach is among the most popular beaches in Chesapeake Bay. With a family-friendly vibe, the kids will have plenty of fun here. Travelling with your love? Enjoy a romantic sunset picnic together at Sandbridge Beach.
What are the top things to do in Chesapeake Bay?
While you'll find plenty of exciting things to do in Chesapeake Bay, it depends on the type of adventure you're looking for. Once you've booked your beach holiday rental, make a list of attractions and activities that interest you and prioritise them based on your preferences, travel companions and available time.
Why should I book my beach holiday rental with Bookabach?
When you opt for a Bookabach beach holiday rental, the only people you'll share your space with are whoever you take with you. It's only you, your closest companions and the whole property to yourselves. Our flexible cancellation policies also mean you can book your rental house with peace of mind if your plans change.