Relax on Martha’s Vineyard at Winnetu Oceanside Resort

It’s a rare thing anymore to feel like you can go off the grid — to feel truly disconnected and relaxed; to find some place that is a world away from the to-do lists, commitments and chaos of everyday life. But that’s what Winnetu Oceanside Resort, a family-owned boutique property on Martha’s Vineyard, does so beautifully. Upon boarding the ferry from the mainland to the Vineyard, something transformative happens. The stress of everyday life melts away as you take in the salt air, admire the iconic New England coastal views, sail away from the concerns of everyday life and step foot into the grand shingle-style hotel on South Beach in Edgartown, Massachusetts.

A seasonal resort open from mid-May through mid-October, Winnetu is the ideal place for busy families looking for a moment of calm. It makes an outstanding multigenerational trip that produces memories and a sense of nostalgia that will continue to bring your family back year after year.

Family-Friendly Review and Highlights of Winnetu Oceanside Resort

A Seasonal Escape that Beckons Families Year After Year

When more than 40 percent of your clientele are repeat guests every year, you’ve done something very, very right. In Winnetu’s case, they have done many things very right, starting with the grounds and location. Situated on 11 acres of rolling green space that leads right down to the ocean, the resort is the Vineyard’s only hotel at the beautiful South Beach. While Martha’s Vineyard can get busy during the summer season, guests never feel the crowd when staying on the large property, which features 54 rooms, suites and cottages as well as 70 privately owned townhouses, duplexes and single-family houses. The Winnetu team does a phenomenal job of making guests feel like family and making every visit feel like coming home. After all, the Winnetu Management Team alone, collectively, has more than 143 years working at this property, which opened in the summer of 2000. They know how to curate the perfect New England vacation that families long for as the school year starts to wind down and Memorial Day approaches.

In addition to the fantastic staff at Winnetu, what keeps families returning year after year? It’s the summer clambakes on the lawn. The tradition of antique fire truck rides down to the beach. Daily lemonade and cookies in the lobby. The ease of biking into timeless downtown Edgartown for a meal, ice cream or shopping. The special family dinner at the The Dunes (former President Obama dines here regularly, just FYI). The rich, complimentary children’s day program that offers activities like field games, pirate treasure hunts, kayaking, water relays, sandcastle contests and more. The short walk to South Beach with lounge chairs and a picnic basket for a day by the ocean. Evening s’mores around the fire. The heated pool and jacuzzi after a big beach day. The ability to play pickleball, table tennis, foosball, chess, basketball or tennis any time of day. The indoor activities center featuring Skee-Ball, arts and crafts, air hockey and loads of toys when you need a break from the sun. Put these things together and you have a picture of the quintessential summer getaway. It exists at Winnetu.

Accommodations

One of the beautiful things about Winnetu for families is the number of accommodation options available for groups of every size. It is a dream destination for extended families traveling together. The hotel’s spacious suites and cottages, privately-owned townhouses, duplexes and single-family homes all come with full resort privileges, including access to the children’s day program.

Within its shingled walls, Winnetu offers hotel studios (great for a couple) or one- to four-bedroom hotel suites. The suites feature full kitchens or kitchenettes, dining and living areas, and decks or patios. The largest of these, the Nobska Suite, covers 1,500 square feet and sleeps up to 15 guests. It features four and a half baths, three kitchenettes and three decks.

Charming and unique one- and two-bedroom private cottages are a fantastic middle ground for families who want proximity to resort amenities as well as privacy. They’re located along beautifully manicured garden paths just steps away from the hotel’s heated pool, tennis courts, main lawn, hotel lobby, The Dunes Restaurant and the General Store.

Our family of six stayed in “Chappy,” a luxurious and fully outfitted two-bedroom cottage. It offered an incredible amount of space while feeling private, yet close enough to allow our older kids, ages 12, 11 and 9, to explore the hotel surrounds on their own. The cottage’s main living area has a full kitchen, three full bathrooms, cathedral ceilings, large windows, a gas fireplace and sliders leading out to separate private patios from the living area, master bedroom and guest bedroom. A pull-down twin bed — which the kids found utterly cool — allows for additional living space and comfort.

The interior of the cottage evokes a soothing island feel and is decked out with excellent books (both kids’ and adult options), board games and flat-screen cable TVs, with popular streaming services coming soon. The cottage also features a large dining table and chairs, a master bedroom wet bar, a gas grill, a private outdoor shower, a washer and dryer, beach chairs and beach towels, and high-speed internet.

If it’s maximum space and privacy you’re after, Winnetu also offers duplexes and townhouses that sleep up to eight guests, and full homes that offer two to four bedrooms, spacious living areas and multiple bathrooms. The largest of these sleeps up to 12 guests, and some homes offer water views.

On top of all these options, it bears mentioning that the resort is also pet-friendly. We brought our golden retriever with us and he was loved on by staff, welcomed on the fire truck rides and treated like a king at every turn. Only certain accommodation options allow pets; check with the Winnetu staff on which ones will suit your furry friend before booking.

Dining

Guests will enjoy world-class, locally inspired cuisine, as well as a beautiful ocean view overlooking South Beach, at The Dunes, which is just above the hotel lobby in the main building. The restaurant is open for à la carte sit-down breakfast daily and for dinner on Thursday through Tuesday evenings (reservations required). The dinner menu features local oysters, ceviche, lobster tacos, chowder (made with Vineyard quahogs, double-smoked bacon, celery, leeks and new potatoes), diver scallops and several mouth-watering non-seafood items as well. The Dunes also offers a reasonable children’s menu with all of the kid-friendly favorites we love, such as chicken tenders, mac and cheese and more.

A huge benefit to dining at The Dunes is the Kids’ Corner activity area, where kids can entertain themselves with games, movies and crafts after finishing their meal at at lighting speed. During peak season, the Kids’ Corner is staffed, and parents can relax and enjoy a decadent dessert or cocktail indoors or outside by the fire pits on the terrace.

Lunch is offered at The Pool Grill from 11 am-3 pm every day, with beverage service from 11 am-5 pm. Guests can enjoy poolside service right to their lounge chair or cabana. The General Store adjacent to the hotel lobby also offers grab-and-go breakfast and lunch options (the fried chicken sandwich is our fave) when you’re feeling informal or to assuage that massive growing appetite that your newly-turned teen has just adopted.

Every morning from 7:30-10:30, Winnetu offers complimentary tea and coffee in the lobby. Every afternoon, they offer lemonade and cookies in the same spot — a real treat for the kiddos! Wine and cheese is also available every Wednesday from 6-7 pm.

Last but certainly not least, the resort offers a signature Wednesday night clambake experience for the whole family during peak summer season. Live music, a rolling green lawn, a beautiful evening under the stars and amazing cuisine make the Winnetu clambakes truly special. Executive chef Richard Doucette goes out of his way to deliver the best of what the local area offers. Feast on lobster, mussels, littleneck clams, corn on the cob, grilled organic chicken breast, New England clam chowder and so much more. The clambakes are far and away Winnetu’s most popular weekly event.

Amenities

Winnetu offers so many fantastic amenities that you could stay on property for a week and not feel the need to go elsewhere (although downtown Edgartown is only three miles away via a very safe bike path, and the resort offers bike rentals so that you can explore the island). The hotel also offers a free daily shuttle to downtown Edgartown that runs every hour during the day, and every half hour in the late afternoon and evening. This a major plus when you want to go a little farther afoot, yet you don’t want the hassle of parking downtown.

An oceanside resort, Winnetu is a short walk via a beautifully forested path to South Beach, one of the Vineyard’s longest and most spectacular beaches. The hotel provides beach chairs and beach towels for guests. The lawn is home to bocce ball, soccer, daily yoga, an apiary and a fantastic pond that the youngest guests will love to explore — turtles and frogs, oh my! Winnetu also offers a fitness room, a pickleball court, tennis courts (with pee wee and adult tennis clinics from late June through early September), a heated outdoor pool, a hot tub, a life-size chess board, an indoor activities center for kids featuring foosball, air hockey and basketball, a large pirate-ship playground and an outdoor area for kids with water tables, play equipment and more.

A complimentary toddler program for kids and parents is available in late May and mid-September, and a complimentary supervised children’s morning program is offered from 9 am-12 pm every weekday from late May through late August. This children’s program is split up by age level (3-4 years, 5-6 years, 7-8 years and 9-12 years) during peak season and offers activities curated specifically to the child’s age and general interest. The program is one of the reasons guests return to Winnetu year after year — kids fondly remember the staff and the wonderful experiences on-property and via field trips, while the parents appreciate the ability to take a moment for themselves.

Local Area

Getting to Martha’s Vineyard is an adventure for the whole family. You can take a ferry from New Bedford, Falmouth, Hyannis or Nantucket, Massachusetts; New York, New York; or Quonset Point, Rhode Island. Some ferries allow you to take your vehicle to the island (book the car ferry early to guarantee a spot); others are passenger-only ferries. Martha’s Vineyard also has a small airport that some major airlines seasonally service from Boston, New York and Washington, D.C. Once you arrive on Martha’s Vineyard, it is easy to get a taxi or an Uber to Winnetu. The resort lists all arrival options on its website here.

Martha’s Vineyard has become a favorite retreat of U.S. presidents, playwrights and other notable personalities. It’s a haven of peace and quiet, with white-sand beaches, charming New England towns and great places to eat and drink. Although it lies only six miles from the mainland, there is something magical about getting on that ferry and finding yourself in what seems like a different world — one with a much slower and more appreciable pace.

The Winnetu Oceanside Resort is a member of Little Gem Resort properties, a family-owned resort collection created by the Snider Family to bring travelers together to experience the joys of island life. Guests can experience Little Gem Resorts at the Winnetu on Martha’s Vineyard, the Nantucket Hotel & Resort in Nantucket and the Lovango Resort and Beach Club on St. John in the U.S. Virgin Islands.

Relevant Links:

Browse all ideas for Massachusetts family vacations on Ciao Bambino

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5 cozy resorts in New England with extraordinary family activities year-round

10 fun things to do in Newport, Rhode Island with kids

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Editor’s Note: Loren was hosted by Winnetu Oceanside Resort to review the property. As always, our opinions are our own on Ciao Bambino. Photos by Loren Braunohler.