There are many, many threads on this. Much depends on a plebe’s personality and how he or she likes to recharge and relax.
A plebe may well just want to get out of uniform, hang in a cool hotel room, take long showers, nap, catch up on social media, nap, eat favorite foods, nap. Have quiet time with just a few people who aren’t asking him questions. Most plebes will not want to go back on the Yard for any reason, unless they have to, so touring family around, in uniform, in Annapolis or DC, on a hot August weekend, is not the mental break they want or need.
Also be open to any “orphan” plebes whose families are unable to come. There are wonderful stories of these plebes being folded up into a classmate’s family for an escape from the Yard.
Annapolis Accommodations and AirBnB are both good options to book a place to accommodate the family. You can get breakfast things in, cook favorite meals, have snacks, have room to spread out, do emergency laundry (white uniforms!) - and not compete with 1000+ other plebe families going out for breakfast, lunch and dinner in a small town. There are many options in Annapolis within walking distance of the Yard or a quick drive, or big homes on the water complete with water toys and outdoor kitchens.