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East Coast Vacations: Easy Summer Escapes from Memorial Day to Labor Day Weekend

Fresh lobster rolls, colonial cottages, sea breezes at sunset: there is a certain magic about summer on the East Coast. Whether you prefer the beach or the country—or a mix of the two—the Northeast has it all for families, friends and couples alike. The following are a few of our favorite destinations for easy East Coast vacations—whether you’re planning a long weekend getaway or an extended escape. These stylish properties—a mix of Indagare favorites and buzzy new openings—are all within driving distance of New York, Boston and points East, and they still have rooms available to book now for the upcoming season. Starting Memorial Day Weekend, here’s where we’re headed.

Contact Indagare for assistance planning East Coast vacations and long weekends this summer. Our specialists can book you at the hotel that is right for you and plan great meals and activities.

Gurney’s Newport, Rhode Island

“The latest news in town is the opening of Gurney’s Newport, an addition that brings a heavy dose of trendiness to Newport’s aforementioned lack thereof. The property is only a ten-minute taxi ride from Newport, and has its own 22-foot marina, sailing school and indoor/outdoor pool.” — Indagare’s Blair West

For a seaside getaway that combines New England tradition with historic glamour, look no further than Newport. The summer destination of choice for families like the Vanderbilts, this idyllic town is especially suited to architecture lovers, who can explore the extravagant mansions on the three-and-a-half-mile Cliff Walk trail. Those seeking a younger scene will find one at Gurney’s Newport, an outpost of the popular Montauk establishment that opened in 2017 just outside the town center on its own island. The property’s seaside Pineapple Club, with its splashy restaurant and bar, is the place to party during the day, while its Scarpetta restaurant welcomes families and couples alike for a festive and delicious dinner. Read more and contact Indagare to book.

Related: Newport, RI: Where to Stay, Eat and What to Do

Ocean House, Rhode Island

“I love the Ocean House for its quintessential New England charm. The wraparound porch is one of my favorite features—it’s the perfect spot to enjoy a morning coffee or afternoon cocktail on a summer day. Most of all, the Ocean House is a great destination for couples or families with varied interests: the property is small enough that you can mingle with other guests if you wish, but large enough to maintain a sense of privacy if you prefer to enjoy one-on-one time with a companion.” — Indagare’s Caroline Barry

In its early days, this iconic resort, which opened in 1868, was the playground of monied aristocrats and members of the East Coast elite, who appreciated its prime location on the Atlantic, subdued glamour and discreet privacy. Parasols have given way to blue and yellow beach umbrellas, and the sand is now dotted with cabanas equipped with butler service, but the past is still present in the Victorian-style main building, despite the modern amenities that have been added to ensure a five-star experience. This summer, the property is hosting a range of events for all ages—including foraging and cooking classes, croquet and cocktails, movies on the beach and lobster boils and barbecues. Those looking for a cozy, luxurious seaside escape with classic New England charm will find it at Ocean House, looking out over the bluffs of Watch Hill. Read more and contact Indagare to book.

Related: The Top 10: Multigenerational Trips

Hotel Pippa, Nantucket

Spicing the unassuming, weathered charm of an old whaling community with a healthy dash of elegance and style, Nantucket is a knockout destination for a long-weekend escape in the Northeast. Last summer, a local couple launched Hotel Pippa off Centre Street, providing a buzzier, more accessible alternative to the iconic White Elephant and stately Greydon House. Guests of the boutique property as well as visitors will enjoy its Petrichor Wine Bar, which is helmed by one of the island’s top sommeliers. Another new attraction: contemporary-art gallery Casterline Goodman, which opened just across the street from the hotel. In between sailing, shopping and lounging on the beach, make time for meals at Indagare’s favorite restaurants—including Straight Wharf, Cru and Galley Beach—and special events like the Nantucket Film Festival (June 19–24), the Boston Pops concert (August 10) and the Nantucket Project conference (September 19–22). Contact Indagare to book.

Related: Nantucket Travel Tips: Where to Stay, Eat and More 

Greydon House, Nantucket

Greydon House has managed to honor Nantucket’s steadfast spirit with thoughtful design. In a tide of sameness, few properties reflect the essence and history of this tiny island as lovingly as Greydon House does.” — An Indagare member

This intimate 17-room hotel opened in the fall of 2016 and is now one of the best properties on the island for a classic Nantucket weekend. Housed in an 1850’s Greek Revival building whose renovation was entrusted to dynamic design team Roman and Williams, the downtown property celebrates Nantucket history while having its own high-end accents, such as hand-painted Portuguese tiles lining the showers, gorgeous lacquered accent walls, dark wood paneling, beachy linens and original art throughout. Other traditional yet playful touches include complimentary beach bags (packed with towels, beauty products and Bose speakers) and an excellent seasonal restaurant helmed by a Michelin-starred chef. Read more and contact Indagare to book.

Related: First Look: Greydon House

Hero Beach Club, Montauk

For the New York weekender, there’s no place like the Hamptons. Although each of these beach towns has its own personality (and its own dedicated set of fans), all are experiencing a boom in tourism development that has pushed them to find ways to protect their roots while welcoming new openings. Nowhere is this balancing act more evident than at Hero Beach Club, which debuted in Montauk in 2017 as the chic yet tranquil rejoinder to the formerly quiet town’s growing party scene. In addition to unwinding in the relaxed atmosphere, Hero Beach Club guests can participate in surfing lessons, fishing, horseback riding and biking—as well as day trips to places like the Wölffer Estate vineyard, for tastings and meals at one of its many restaurants. Other big Hamptons debuts to look out for this summer include Journey in East Hampton and Shou Sugi Ban House, a 13-room wellness hotel opening in Water Mill. Contact Indagare to book.

Related: The Best New Hotels and Restaurants in the Hamptons: Summer 2019

Glenmere Mansion, New York

Glenmere is a lovely, quiet, adults-only weekend respite just a 90-minute drive from New York City. For those who want a more active getaway, I recommend exploring the Hudson Valley by car, with a stop at Storm King Art Center (a 30-minute drive away).  In the afternoons, guests can enjoy the spa, read a book by the pool, walk the grounds, or play a game of bocce in the back garden. Indagare Tip: Come on the weekend, since the formal restaurant, the Supper Room, is only open from Thursday to Saturday.” — Indagare’s Lizzie McGirr

Opulent but tasteful, Glenmere is a romantic retreat on the western side of the Hudson River with a spa and restaurant. Built like an Italian villa, the grounds are distinguished by well-clipped garden paths and marble fountains, while the interiors have Gilded Age details such as moldings and grand fireplaces, plus custom Loro Piana curtains and plush beds for sleeping in. Guests who come on the weekends can explore the sprawling 150-acre grounds and take advantage of the resort’s pool, two Har-Tru tennis courts, championship croquet court and spa services. In addition to the formal Supper Room restaurant, guests should not miss dinner at Frog’s End, a tavern on property that was modeled after one of F. Scott Fitzgerald’s haunts on the Cote d’Azur. Read more and contact Indagare to book.

Related: Melissa’s New York City: Where to Stay, Eat, Shop and More

The Point, Adirondacks

“The Point has the most comfortable rooms I have experienced anywhere; it is hard to tear yourself away from the coziness of the fireplace. We have visited many times, and each occasion has been unique, but the common thread is the incredibly peaceful surroundings and the amazing staff.” — Indagare member and longtime visitor-turned-owner of the Point, Laurie Lapeyre

Located on a 75-acre peninsula on Upper Saranac Lake, this 11-room retreat (which once hosted the Rockefellers) is now a popular destination for well-heeled families looking for an authentic camp-style property with all the amenities of a luxury hotel and an elegant five-star atmosphere. Guests stay in the property’s original log cabins with rustic-chic décor. Although each of the 11 rooms possess their own unique charm, the most popular to book is the “Boathouse,” an airy space with a canopied bed that sits right on the water. In summer, the peak season, days are spent hiking, playing croquet or boating on the lake, followed by dinner in the elegant restaurant, which hosts twice-weekly black-tie events. Contact Indagare to book.

Related: On the Road With…Teens

Twin Farms, Vermont

“With its classic New England landscapes and private accommodations, Twin Farms feels like your own Vermont country house, with a standout art collection and a caring staff—but the true standout at this retreat is the food. Meals revolve around healthy, locally-sourced, seasonal ingredients, and the chef takes charge every evening with a surprise dinner presentation (there are no menus). While the main dining room is lovely, you can also request to eat in front of the fireplace or on the porch of your suite—or, for a special occasion, reserve the private Wine Cellar.” — Indagare’s Elizabeth Harvey

Located on 300 bucolic acres, this all-inclusive retreat is adults-only, except for two annual “family weeks”: one each in summer and winter. In addition to beautiful suites and cottages, the property boasts museum-quality art, including works by Jasper Johns and Roy Lichtenstein, plus a much-lauded (and healthy) culinary program. The kitchen’s focus on local and seasonal ingredients is unparalleled, producing such delicious dishes as porcini poached Vermont turkey with wild mushroom lentil ragout and cold poached Maine lobster with potatoes in truffle vinaigrette. Onsite activities include hiking, canoeing, croquet, tennis, fly-fishing and spa treatments. Indagare Tip: When you go out for a hike, request a picnic lunch, which the staff will prepare for you at the end of the trail. Read more and contact Indagare to book.

Related: The Top 10: Mother-Daughter Trips

Mayflower Inn & Spa, Auberge Resorts Collection, Connecticut

“The Mayflower Inn & Spa is such a wonderful and easy trip for a romantic weekend or Mother-Daughter getaway. We always have a great time there, and the spa services are amazing.” — Indagare member Leigh Johnson

Located in Litchfield County (just a two-hour drive from New York City), this classic, 30-room hotel celebrates the surrounding landscape and New England heritage while encouraging its guests to truly relax and indulge themselves. Offerings include wine tastings, private meditation sessions, a full range of exercise classes and a 20,000-square-foot spa, plus, in summer months, a pool, tennis court and putting green. Guests can also hike the property’s 58 acres of landscaped gardens—on their own or accompanied by an expert naturalist—and picnic on a cliff overlooking Lake Waramaug. Read more and contact Indagare to book.

Related: Summer Spotlight: Block Island

White Barn Inn, Auberge Resorts Collection, Kennebunkport, Maine

“The White Barn Inn was one of my dad’s favorite places. We really enjoyed visiting and remembering why he loved it: you can always get a cup of coffee (essential for early risers), nothing is pretentious and the food is exceptional. Although other properties in New England may offer better activities, outdoor space and updated rooms, the White Barn Inn is so comfortable and has amazing service.” — Indagare member Lynn Thomas

Unlike the Hamptons and Nantucket, the harbor village of Kennebunkport is a New England escape that has remained low-key and laid-back, despite being the summer destination of choice for such figures as the late president George H. W. Bush. The emphasis here is on savoring a slower pace of life, feasting on freshly caught lobster and embracing the peaceful Maine woodlands and coastline, with a handful of lovely shops and excellent restaurants—all of which makes it the ideal getaway for young families and couples. This 26-room historic inn is a charming place to stay while visiting, and it consists of several classic clapboard cottages, a converted carriage house and the main inn, which are linked by flower-lined walkways and gardens. Particularly lovely are the junior suites, which have gas-burning fireplaces and large bathrooms with soaking tubs. Possible activities during your stay include a sunrise picnic breakfast on the beach, a guided bike ride (anywhere from 20 to 80 miles) followed by a deep tissue massage, and private cooking and mixology classes. We also love Hidden Pond and Cliff House as other options. Read more and contact Indagare to book.

Related: The Top 10: Prettiest Beaches in America

Contact Indagare for assistance planning these East Coast vacations and long weekends this summer. Our specialists can book you at the hotel that is right for you and plan great meals and activities.

– Elizabeth Harvey on May 14, 2019

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Whether you prefer the beach or the country—or a mix of the two—the Northeast has it all for families, friends and couples alike.

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