Winnetu Oceanside Resort

The 18 Best Family Resorts in the U.S.

"Family‑run since the late 1960s, this seasonal property on Martha’s Vineyard offers a warm, timeless hospitality with 11 acres of landscaped grounds, a private stretch of South Beach, two outdoor pools, cottages and larger rentals for multigenerational groups, and a complimentary daytime drop‑in program featuring counselor-led activities like sandcastle contests, pirate crafts, and tie‑dying. Guests can take water taxis to Edgartown, cruise coastal trails on two‑wheelers, join an oyster‑farm tour, or indulge in a massage while kids play. Before departing, families can take rides in vintage vehicles such as a 1931 Model A Ford bus or a 1956 pumper fire truck. Accessible ground‑floor rooms are available; rates start at about $325 per night (seasonal operation mid‑May through mid‑October)." - Sarah Bruning Sarah Bruning Sarah Bruning is the special projects and surveys editor at Travel + Leisure, where she has been on staff since 2018. She assigns stories across the magazine, primarily for the Experiences section and feature well. Travel + Leisure Editorial Guidelines