I usually leave my car on the mainland and bring bicycles out to the islands. Both islands have tons of bike trails and flat terrain. It’s perfect. Just get a taxi to move my bags for me, or the hotel itself.
And what Merrill says is true: it just gets nicer, the architecture prettier, the beaches better, etc. once you’re over the bridge onto the Cape.
I love Welfleet and Chatham.
Much prefer Nantucket to Martha’s Vineyard…
TTT
Agree with inclusion of this location for vacation consideration.
I just looked and for our dates, there are 2 listings available: $1,200 & $1,300/night. I’m not a baller like that!
Rent a house for a week, for much cheaper than that per night.
I ain’t no balla, neither.
Crescent Beach is perfect for kids. The restaurants are casual, affordable, and quite good.
You can bring a car onto the island for $35 each way. And you avoid the stupid Figawi crews on Nantucket.
Poppy - Take a look at VRBO and Airbnb as there are many more listings. That said many places on Cape Cod and the Islands, along with Block Island, have repeat customers every year and they book early. Nearby large metropolitan areas have droves of people seeking beaches in summer. Also pay attention to the weekly check-in and out as many are Sat to Sat.
If you want the baller experience try the Ocean House in Watch Hill, RI … About Our Luxury Hotel in Rhode Island Serving All of New England .
Be very careful about using VRBO, HomeAway, or FlipKey.
Use local real-estate agents, instead, notwithstanding my usual descriptions. Sullivan Realty, on Block Island, from which I have rented for almost fifteen years, is very good.
Have you looked into Chatham? Has very nice beaches and a very walkable downtown with cute shops and restaurants.
Chatham Bars Inn? Memories. (Expense account from the now-defunct Digital Equipment Corporation.) I can only describe myself as a survivor of that corporate experience.
Good family atmosphere but probably pricey, in Chatham, as Nantucket.
I can’t speak specifically to Onset, but the outer cape is a unique experience. A relatively narrow sand bar stuck way out in the ocean with a calm bay on the west side (much better for a 5 year old). Sunset and sunrise over the water. It’s hard to describe, but it is very special.
I’m not sure why you’d fly all the way across the country just to be in a regular Atlantic Ocean shore town. We went last summer to Salem and Gloucester, in part because that’s the closest spot to us on an ocean, and we had limited time and energy. You already have the Pacific in your back yard.
I have a friend (sadly not a close friend) who has a house on Martha’s Vineyard. I don’t know how much the house cost, but the initiation fee for the golf club was $1M.
I really agree with this… once you’re in Sandwich the character changes, but once you’re on the outer Cape (Chatham north) or the Islands it really is great and feels like something different. I’m only a 2 hour drive from the Cape and I don’t make the trip just for the South Shore of MA somewhere.
Thanks for all the advice! I just booked a house in Chatham just a short walk from the beach.
You’ll really like Chatham. I disagree with whoever said the Cape starts at Eastham and, as I said, I’ve spent a lot of time there. Still have family in Hyannis and Dennis, and my grandparents are buried about 15 minutes from Chatham.
No disrespect intended, but the perspective is a little different when you are a Californian as opposed to a New Englander who is accustomed to many coastal towns. Chatham is a classic Cape Town and kind of central. If you want you can day trip up to Provincetown, and if you really wanted an adventure you can drive to Hyannis and take a ferry over to MV or Nantucket for a long day trip. But there are nice beaches and nature all around Chatham.
I would definitely check out Impudent Oyster in Chatham and if you make the trip to P-Town Blackfish in Truro is the best restaurant on the cape.
Truro Vineyards was a nice place to relax in the sun on the lawn with some local wine and cocktails. Kid friendly and room to run around.
+1 to all the Wellfleet recommendations… although I’m sure you’ll enjoy wherever you choose.
For our weekly trips we always try to eat at the Impudent Oyster and grab a drink outside at CBI. I would also recommend bringing some wine and getting you lobster roll / fried seafood fix from Sesuit Harbor in Dennis as its one of the few BYO on the cape. I would day trip it to Wellfleet and either do Maconi’s beach or the Sancuary and then grab Oysters at Mac’s or Mobys’s (BYO).
I second the Raw Bar/Sesuit Harbor Cafe.
Thanks all! I will mention that we are a vegetarian family. 
So, um, best pizza recommendations on the cape?
Talkative Pig in Chatham.
Ember in Harwichport.