East Hampton Point (from $300), a secluded waterfront resort on Three Mile Harbor, seems made for families: Its thirteen wicker- and floral-filled cottages come with separate master bedrooms, kitchenettes, and pull-out sofas (ask for No. 6, stocked with a Jacuzzi tub and full sleep sofa). Once you’ve settled in, bundle up for a walk on the windy bay beach—perfect for kite-flying.
It’s all about location at the Tudor-style Southampton Inn (from $150), an easy walk from the Hampton Luxury Liner bus drop-off, the train station, art galleries, restaurants, and boutiques. The hotel’s 90 rooms desperately need updating and staffers are sometimes less than hospitable, but families can make use of connecting rooms and pets are welcome.
The accommodations at kid- and pet-friendly Baron’s Cove Inn (from $95) in Sag Harbor are standard-issue motel. But visitors don’t spend much time in their rooms—even in the waterfront duplex with its views of the marina. Take a family stroll over to the Ice Cream Club on the Long Wharf, then cruise Main Street’s throwback nautical shops.