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My Uncle lives in Rehoboth Beach, DE, so I grew up going to the beach there. There are plenty of houses for rent in Rehoboth or neighboring Dewey Beach which is less crowded and family friendly. There is a large wood boardwalk in Rehoboth, and it is a short (maybe 15-20 minute) drive to Lewes where you can board a ferry to go to Cape May. We mostly went to the beach and hung out at my uncle's house, so unfortunately I don't have a lot of input for other activities.

The Cape is great and we go almost every year. I'd highly suggest trying to time it so that you aren't driving to/from the airport on the weekend though. The traffic on the drive down is always the worst part for me. Nantucket is so lovely and you could fly directly from Logan and avoid traffic altogether. It's a bit sleepier there than on the Cape itself.

I've run into 3 people who went to Maine on vacation this past summer and said that it's a must to do once the boys are older. I'm looking forward to that.

We vacation in Avalon, NJ every year and we LOVE it. Avalon is north of Wildwood and Cape May. It's a little more upscale than Wildwood, but not as much history as Cape May. The nice thing about Avalon is that the town is very walkable as long as you stay within a few blocks of it, and you can rent a large house with a pool easily. You're also about a half hour from Ocean City where there's a boardwalk and rides for the kids. Wildwood is about 15 minutes south, and Cape May is also about 25 minutes south. The Cape May County Zoo is free and within about 15 minutes.

We'll go to the beach a few days, then take the kids somewhere. We also rent bikes and ride down to Stone Harbor with the kiddos in the trailer behind us. There are a ton of water sports and fishing excursions that you can do, and the Jersey Shore points have such cute shopping areas. I'd recommend it in a heartbeat!

I can only chime in for Hamptons/Eastern Long Island since I live an hour or so away...

I don't know about budget, but of Hamptons is expensive, Montauk/Greenport/North Fork areas are all lovely. If everyone can get into cars, the possibilities are endless. You can beach town stuff, fishing, shopping (there is a big outlet), splish splash, wineries, farms for kids.... So much to do! The only thing is coming from NYC airports it's def gonna be a bit of a drive depending on when. But I feel like everything you listed will not be that close to the major airport anyway.

I live in Maine so I’m obv biased but Maine is pretty close to Heaven in the summer and definitely has all you mentioned above (as well as lobster rolls cheap lol).

So Portland is a 2 hour drive from Boston Logan (but there are also busses and an Amtrack train that you can take vs. driving). Portland also has a really nice little airport served by most of the airlines. There are tons of rental homes on the millions of lakes out here, many of which have nice sandy beaches. Then of course is the coast and sandy beaches and rocky beaches.

If you stay near Portland, you’re also well situated to (day) travel to many places. Portsmouth, NH (which I LOVE) is only 45 minutes away. VT is like 3 hours away, Boston 2, even Canada is only a 6 hour drive.

Bar Harbor is about 4 hours from Portland and it’s beautiful but also REALLY expensive in the summer and books up very early. From up there though you can access Acadia if you want any level of hiking (easy to insane).

Boothbay Harbor is another coastal city we like a lot; as well as Rockland/Camden and Belfast.

Most larger (relative term!) cities on the coast will have fishing charters, whale and nature watch boats, etc. All of the cities I mentioned above definitely do and all also have really charming little downtowns.

There is very little pretentiousness anywhere in Maine. Portland is a foodie-haven and even there there is only one restaurant I wouldn’t bring my LO to, because I know they will be pretentious but no one else (even the white linen places) are pretentious at all. Many won’t have children’s menus but will gladly make something simple like pasta or whatnot for kids if you just ask.

Finding a vacation rental house with a pool might be a real challenge.t. Some resorts have more individual/small buildings versus like just hotel rooms and would be more likely to have pools. Pools are not very useful up here so most places won't have them.

Aww I was going to say North Fork before I saw you've already been lol. We love it now that we have kiddos-- we've gone the past 3 summers. Super laid back and kid friendly but fun adult stuff too like delicious food and vineyards/breweries

What about Old Orchard Beach in Maine?

https://oldorchardbeachmaine.com/

There's a bunch of kid-friendly things to do around there too - water parks, amusement parks, mini-golfing. Plus the beach of course!

@Anagram: Portland does have beaches, but it isn’t a "beach-town" in the same way some of the other places you’ve mentioned are. There isn’t like a big beach, or a big beachy area you can walk to from the downtown for instance. There are some “hidden” gems of beaches though in Portland itself. There are also two really nice big sandy beaches about 15 minutes south of Portland in Scarborough, and another about 20 minutes north of Portland in Freeport. There are probably also good beaches in between those towns too; those are just the ones I like the best and go to. You would most likely want/need to rent a car but there are tons of options within 20 minutes of Portland for beaches.

Within Portland itself, check out Mackworth Island (this may technically be in Falmouth, actually) and East End beach. South Portland has Willard beach. In Scarborough, check out Higgins beach, Scarborough State Park and Ferry beach. In Freeport, check out Winslow Memorial Park.

I’m less familiar with the beaches between Portland the NH border just because we don’t need to go that far south to go to the beach, but of course Kennebunk/K'port and Oqunquit are great options too. A beach that’s often mentioned is Old Orchard Beach. Personally, that’s the last on my list because it’s not as nice as the other beaches and also doesn’t have the same vibe as some of the others. I don’t know; I just don’t really like it (and neither do a ton of people up here) though there isn’t anything wrong with it either. It’s also really touristy.