Chesapeake Bay rentals with pool

Choose from 4,902 vacation rentals with a pool in Chesapeake Bay. Take your crew on a fun-filled trip to Virginia Beach or visit other well-known cities like Garrett County and McHenry. Wherever you’re headed and whether you want to swim or float around in the water, Vrbo has your perfect stay.

A number of factors will determine how much you pay for a vacation rental with a pool in Chesapeake Bay, such as the size of the property and how long and when you’re staying. All you have to do is enter your vacation dates and preferences to find a house where you can splash around in.

That all depends on what you plan to do and if you want to visit in peak, shoulder or low season. March is when most people book a vacation rental with a pool in Chesapeake Bay. Average temperatures during this time range between 39ºF (4ºC) and 51ºF (11ºC).

If you want to make a splash after a big day of exploring, have a look at our vacation rentals with a pool in Chesapeake Bay that come with picturesque vistas like views of historic areas.

Pick a cabin with a pool in or around Chesapeake Bay and add another level of fun to your getaway. Comfy and welcoming, our cabins are great for couples and families who are searching for a more outdoorsy experience. Toss in a pool and you can spend your time switching between discovering nature and practicing your cannonballs!

Night or day, enjoy a swim whenever you want when you book a vacation rental with a private pool in Chesapeake Bay. To discover Vrbo properties that’ll add an extra layer of fun to your trip, use our “Private pool” filter.

After you’ve secured your vacation home rental with a pool, it’s time to start planning your Chesapeake Bay itinerary. Think about your interests, whether that’s food experiences, outdoor activities or relaxation and wellness, and plan your to-do list from there. Just make sure you give yourself plenty of time to enjoy long, leisurely days by the pool.

When you choose a Vrbo vacation rental with a pool, the only people you’ll share your living space with are whoever you take with you. It’s only you and the family with the whole place to yourselves having a splashing good time. Also, with our rewards program, One Key™, you can collect and spend OneKeyCash™* on eligible bookings made through Vrbo, Expedia and Hotels.com. Plus, our flexible cancellation policies also mean you can book your rental house with confidence in case your plans change. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Hotels.com, Expedia and Vrbo.