At These Two Family-Friendly Resorts, the Hamptons Aren’t Just for the Jet Set

The Hamptons are known for sprawling mega-mansions and A-list celebrity sightings, but the beachside enclave on the east end of Long Island, New York, is also home to a pair of sister resorts that create space for a different kind of vacationer: families. The Pridwin Hotel and Cottages on Shelter Island and Baron’s Cove in Sag Harbor (both Cape Resorts properties) blend legacy and approachability, with a range of accommodation types, kid-centric programming, and indoor and outdoor facilities for fun and games, making either (or both) the perfect fit for a family getaway.

Photo: Amy Gordon

A far cry from the themed resorts that dazzle kids with loud restaurants and splashy water parks, The Pridwin offers a quiet retreat where families can spend good old-fashioned quality time together. In fact, from the moment I disembarked the ferry on my way to the property, time seemed to pass more slowly. I rolled down the windows, inhaled the salty sea air, and exhaled the everyday stresses I’d left behind on the other side of the Long Island Sound.

As I pulled into the driveway, a small army of staff was strategically placing pumpkins, hay bales, tables, and chairs across the expansive front lawn. They were setting up for the hotel’s Fall Festival, a weekend-long event open to the entire community, complete with potato sack races, bobbing for apples, outdoor movies, and s’mores.

Originally built in 1927, The Pridwin sits on a woodsy 7.2-acre property across the street from the Peconic Bay. Design details like the iconic hunter green shutters around the windows and the framed 1930s-era bathing suits on the walls celebrate the hotel’s storied past, while modern must-haves like complimentary WiFi and in-room USB and USB-C charging stations accommodate the practical needs of today’s families.

In the summer busy season, guests of The Pridwin can hang out by the outdoor swimming pool, lounge on the private beach, go fishing off of two private docks, and enjoy pickleball and tennis lessons. More adventurous visitors can borrow bikes, paddleboards, and kayaks, and family-friendly programming like scavenger hunts and kickball games offer ways for your whole crew to bond. In case of rain, the log-cabin-style Nook game room is stocked with board games and jigsaw puzzles to keep everyone occupied.

Photos: Amy Gordon

A wide range of room types makes The Pridwin an ideal choice for families of all sizes. I stayed in one of the 33 guest rooms in the main building, and while it wasn’t exactly spacious, details from the buttery-soft bathrobe to the complimentary minibar made it feel every bit luxurious. Scattered elsewhere throughout the picture-perfect property, 16 private cottages ranging from studio cabins to two-bedroom duplexes offer roomier spaces with coveted amenities like gas fireplaces, kitchenettes, private decks, and separate living and sleeping areas.

The Pridwin’s trolley bus will drive you to and from local shops and cafes, but you don’t have to leave the property if you want to eat well. The Terrace restaurant overlooks the water and serves Long Island-inspired cuisine for breakfast, lunch, and dinner. In between meals, guests can grab light bites and beverages at The Crescent Bar.

To get to Shelter Island, visitors and their vehicles travel by ferry from either North Haven on the South Fork of Long Island or Northport on the North Fork. Boarding is on a first-come, first-served basis, and tickets are cash-only. Once on the island, The Pridwin is just a few minutes’ drive. If you don’t have a car, accessing this serene slice of simplicity is surprisingly easy. The Long Island Railroad’s Greenport station is adjacent to the ferry dock, and The Pridwin is happy to pick you up when you arrive on Shelter Island.

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Photo: Amy Gordon

Across the Long Island Sound to the south, The Pridwin’s sister resort, Baron’s Cove, is another fantastic choice for families. While this seaside resort feels laid back and removed, it’s actually just a short walk from Sag Harbor’s bustling downtown.

I arrived at Baron’s Cove on a sunny afternoon in October, and the staff welcomed me with beaming smiles and helpful advice. A front-desk agent showed me to my room, where the nautically themed furnishings included a king bed, a pull-out sofa, a kitchenette, and a sliding door leading to a lovely furnished veranda.

Embracing its classic motor-inn heritage, each of the 67 guest rooms opens onto an outdoor corridor. Room types range from standard doubles to king suites with separate living areas and sleeper sofas to rooms with high ceilings and lofted beds. If your pup is along for the trip, the Travels with Charley package includes a dog-friendly guest room with a dog bed, pet treats and toys, and a copy of John Steinbeck’s novel of the same name. In fact, Steinbeck, his wife Elaine, and his dog Charley spent time at the resort when it originally opened in the 1960s.

Serving breakfast, lunch, dinner, and snacks, the Restaurant at Baron’s Cove has a loyal following of both locals and visitors. Adults savor classic American favorites like lobster rolls, braised short ribs, and homemade mac and cheese, while kids can pick from freshly prepared versions of crowd-pleasers like chicken fingers, grilled cheese, and peanut butter and jelly. Adjacent to the bi-level dining room, the patio is filled with Adirondack seating around cozy fire pits that make this outdoor area the perfect hangout spot. During the summer, live musicians play every night, saving parents the hassle of finding age-appropriate activities to keep their little ones entertained on vacation.

Photos: Amy Gordon

To explore the local area, it’s just a 10-minute walk to Main Street, where high-end clothing stores, souvenir shops, and restaurants offer plenty of ways to spend your time (and your money). Back at the resort, families can hang out in the heated saltwater outdoor pool, play a round of tennis, take a yoga class, or borrow bikes.

Baron’s Cove is about 100 miles from Manhattan, which can take between three and four hours by car depending on traffic. The hotel offers complimentary on-site parking. To arrive by train, take the Long Island Railroad to Bridgehampton, and then it’s just a four-mile ride from the resort. Alternatively, the Hampton Jitney leaves from Manhattan and drops passengers off in the town of Sag Harbor, where the hotel will happily send a car to pick you up.

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