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Now would I swim in the bay... I would not.  The sand is soft and squishy, there can be jelly fish, and you have to walk out a good distance to get any real depth (3 - 4 feet deep).  There is also a small beach at Northside Park.  But honestly, the jelly fish scare me away. 

There is a small beach on the bayside called Homer Gudelsky Park located right next to the  Rt. 50 draw bridge. Many people fish there as there is a deep hole about 15 feet off the beach.  Good place for wading and playing in the sand, especially for children.  Quite a few boaters enjoy the bayside of Assateague Island for picnicing and swimming.  In my opinion, the closer you are to the inlet the clearer the baywater.  Seacrets offers a bayside beach for patrons. They have floats and rafts and provide a wait staff to bring you cocktails and food right in the water.  You will also find some folks (me included) who who dig for clams in the bay.  I suggest you wear water shoes when in the bay since it can be squishy and have more shells on the bottom. As for jellyfish, I just try to steer clear of them.  I have been boating and swimming in the bay for over 30 years and I usually see the same amout of jellyfish in the bay as in the ocean.

There are really no public places to swim on the bayside. However, there are a few private places where you can get to the bay to swim or wade. They include the bayside beaches and serving areas at Seacrets and Mackey's and the bayside beach for people staying at the Oceanic Motel at the inlet. Sunset Island, a private community at 67th Street, also has 3 private bayside beaches where you can swim. The ocean beach is 10 miles long, guarded all summer, and free and accessible for its entire length. Have fun in OC!

I have gotten in the water behind the Princess Bayside and it reminded me of swimming in a pond.  Like Savas said, the sand is different, the feel is different.  And yes, there are almost always some jellyfish around. I much prefer swimming in the ocean. If you have a small child that you're concerned about with the ocean, bring along an inflatable pool and fill it with ocean water the little one to play in on the beach.