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’re ideal for that sunny window between Memorial Day and Labor Day. With access to quiet beaches or hiking trails, charming restaurants, buzzy outdoor watering holes and curated boutiques, and historic towns, growing art scenes and nature preserves to explore, these hotels offer havens meant for savoring a true taste of summer (did someone say ice cream?).

Contact Indagare or your Trip Designer to start planning your summer East Coast vacations—this year and beyond. Our team can provide information on the best hotels and rooms to book, restaurant and shopping recommendations and more.

Indagare Adored: Ocean House, Watch Hill, Rhode Island

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. In its early days, this iconic resort, which opened in 1868, was the playground of 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 (the classic wraparound porch remains one of our favorite features; it’s the perfect spot to enjoy a morning coffee or afternoon cocktail on a summer day). For a more privatized experience, we recommend staying in one of the six freestanding cottages, which range from cozy two-bedroom bungalows to stately seven-bedroom homes (some of which are also equipped with their own swimming pools or hot tubs). Read more.

Related: Our Favorite U.S. Hotels with Private Cottages or Villas

On Our Radar: Hotel Pippa, Nantucket, Massachusetts

Spicing up 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. In 2018, a local couple launched Hotel Pippa off Centre Street, providing a more contemporary, more accessible, boutique alternative to the iconic White Elephant and classic Greydon House. 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—which are within easy walking distance, thanks to the hotel’s convenient downtown location.

Related: Summer Road Trip Ideas: The Best U.S. Hotels You Can Drive To

On Our Radar: Faraway, Nantucket, Massachusetts

The nautical aesthetic of the Grey Lady received a seriously chic update in 2021 in the form of Faraway Nantucket. In the heart of town on Centre & India Street, the property is set across four classic New England buildings (the oldest of which dates back to 1846)—but inside, savvy travelers will find a Caribbean-style courtyard lounge where summery cocktails flow freely, and interiors that were inspired by the adventures of seafaring captains. The focus here is, simply, fun. The rooms are outfitted with blond- and painted-wood furnishings, brass fixtures, vibrantly patterned textiles and imaginative wallpapers (as well as Le Labo products). We are especially excited about the rooms with double bunk beds, perfect for families and groups of friends.

Related: The Best New Boutique Hotels in the U.S.

On Our Radar: Life House and Blue Iris, Nantucket, Massachusetts

Less than a 10-minute walk in the direction of Jetties Beach, Life House, Nantucket is another delightful newcomer to the town’s hotel scene. Housed with a 200-year-old Federal-style mansion, the property has been a boutique hotel since 1833—but now it’s helmed by a bright, young hotelier, Rami Zeidan, who is just as focused on the transformative power of travel as he is on the hotel experience. Staying true to the original inn’s layout, the common spaces are small and truly communal—with the highlight being the Garden Terrace, where Marshall speakers and fringed umbrellas flank cozy rattan armchairs. The entire house follows in a floral motif, marrying more traditional Nantucket décor with contemporary sensibilities. The property is also available for private buyouts.

Plus: Last summer, Life House opened a new sister property just a 10-minute walk down Centre Street: Blue Iris. The intimate hotel is located in a Greek Revival-style former private home that was once owned by a local art collector, and the property’s refreshed design pays homage to this legacy with an abundance of Mediterranean decorative touches (including signature Portuguese-style tiles and Murano-inspired chandeliers) and serene spaces for a post-shopping tête-à-tête, like the courtyard garden patio.

Also on our radar: Life House Berkshires, opened September 2022.

Related: Best New Hotels of 2023

Indagare Adored: Greydon House, Nantucket, Massachusetts

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 1850s 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, 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 Michelin-starred restaurant. Read more.

Related: Summer Recipe Ideas from Our Favorite U.S. Hotels

Indagare Adored: Harbor View Hotel, Martha’s Vineyard, Massachusetts

An island icon since 1891, the historic Harbor View Hotel occupies a prized waterfront location at the end of Edgartown’s North Water Street and features unrivaled views of Edgartown Lighthouse. The shingled property is an easy five-minute walk from downtown Edgartown, so guests can frolic at the beach by day and dine in town at night—all without driving, a rarity in Martha’s Vineyard. And the on-site amenities provide little reason to leave; the property features an outdoor pool, fitness center, yoga classes, Children’s Program and multiple dining venues, including Henry’s, an elegant gastro-pub, and Lighthouse Grill, a family-friendly venue with stunning views. Read more. — Emma Pierce

Related: 11 Summer Vacation Ideas for 2023

On Our Radar: Hero Beach Club, Montauk, New York

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), the East End and Montauk have in recent summers seen a flurry of hotel openings that aim to honor the area’s traditions while also bringing fresh perspectives to the mix. Nowhere is this balancing act more evident than at Hero Beach Club, which debuted in Montauk in 2017 as the hip yet tranquil rejoinder to the formerly quiet town’s growing social 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, or meals at one of the brand’s many restaurants.

Also on our radar: Daunt’s Albatross in Montauk.

Related: The 22 Best New Hotels of 2022

On Our Radar: Marram Montauk, New York

Montauk’s most promising boutique hotel opened its doors in 2019 to welcome in surfers, yogis, creatives and stressed-out New Yorkers in need of a restorative beach vacation. Here, the ethos is barefoot-luxury, manifested in the warm (and irresistibly chic) décor, the minimalist design concept that emphasizes the 96-room property’s direct beach access, and the entertainment program, which encourages guests to immerse themselves in the hotel’s natural surroundings, through meditation and yoga sessions, creativity/art workshops and an on-property surf school. Don’t miss a meal at the restaurant, Mostrador Marram, a South America-inspired creation whose menu manages to be health-focused and locally sourced, without sacrificing indulgence (we see you, molten chocolate cake). Read more.

Related: Indagare Index 2023: U.S. & Canada

Indagare Adored: Shou Sugi Ban House, Water Mill, New York

The 13-room Shou Sugi Ban House is a new Japanese-inspired destination spa that opened between Southampton and Water Mill. A zen escape with a ryokan-esque sense of place, it offers packaged wellness retreats and is perfect for travelers looking to rest, reset and take a holistic approach to their health. The beautiful property appeals to design lovers and foodies, too—Mads Refslund, co-founder of Copenhagen’s Noma, is behind the spa’s popular culinary program, and the hotel is located next door to the acclaimed Parrish Art Museum. The property itself has Japanese gardens, winding rock pathways and an eight-ton buddha sculpture from Bali, and the facilities and rooms feature a neutral color scheme and minimalist aesthetic. The rooms are centered around a small pool, and have floor-to-ceiling windows, sleek furnishings, gas fireplaces, indoor and outdoor showers and either a hinoki ofuro (Japanese soaking tub) or regular bathtub. Read more.

Related: Health and Wellness Tips from Our Experts: Indagare Global Conversations

On Our Radar: Canoe Place, Hampton Bays, New York

Also generating major buzz is a country-club-chic reincarnation by Main Street Hospitality of Canoe Place—which is alleged to be “America’s oldest inn,” established in 1697—in Hampton Bays. With a curation of historic art, new dining and bar concepts, manicured gardens and an outdoor pool, this property has the potential to become Southhampton’s new spot. Rooms include guest accommodations in the Inn, freestanding cottages and residence-style boathouses.

Indagare Adored: The Chequit, Shelter Island, New York

In celebration of its 150-year anniversary, Shelter Island mainstay The Chequit began unveiling the results of a full restoration last summer, under new ownership (Stefan and Stacey Soloviev, who own extensive property across the North Fork, including Peconic Bay Vineyards). Founded in 1872, The Chequit has lived many lives, including as a sleepy bed-and-breakfast and as a glamorous scene spot that used to welcome the likes of Marilyn Monroe, Arthur Miller and the Kennedys. This latest reincarnation includes a thorough aesthetic refresh (focused on Scandinavian design elements, blonde wood accents, and a fresh, creamy color palette); luxe amenities like Frette linens, rain showers and clawfoot tubs, Malin + Goetz bath products and sound-proofed windows with blackout shades; and new dining concepts, including a Japanese restaurant, Weakfish; the classic Tavern, including a nostalgic, wood-paneled lounge and an open-air, harbor-facing terrace; and a casual café and wine bar.

Also on our radar: The renovation of The Pridwin, also on Shelter Island.

Related: What’s New in the Hamptons: Summer 2022

On Our Radar: Valley Rock Inn & Mountain Club, Sloatsburg, New York

Just an hour’s drive north from Manhattan, the Valley Rock Inn is a charming and historic property nestled in the foothills of the Ramapo Mountains, with 70,000 acres of parkland (filled with lakes and trails) surrounding. Focused on wellness and organic farming, the property provides a quiet retreat, with the accommodations currently available including four private guesthouses, each equipped with three-to-five bedrooms and a private pool and dining area. There is also an on-property gallery and several lovely gardens, where guests can reserve an atmospheric lunch or dinner.

Also on our radar: An installment of The Ranch’s signature fitness and wellness program in Hudson Valley, coming March 2024.

Related: 16 Best New Boutique Hotels in the U.S.

On Our Radar: The Lake House on Canandaigua, Finger Lakes, New York

In the Finger Lakes—an up-and-coming wine region that has lately enjoyed renewed popularity among sophisticated travelers seeking to venture off the beaten path—The Lake House on Canandaigua is a design-focused, waterfront property masterminded by the siblings Bill and Lyndsay Caleo (of the real estate development firm The Brooklyn Home Company), with interiors by Post Company. The property revolves around the simple, timeless pleasures of lakefront life—kayaking across the lake’s cool, smooth waters; curling up in the library with a good book; listening to the crickets and crackling wood around an evening bonfire—but it brings a contemporary sense of style to the area, along with a focus on wellness and sustainability. In addition to traditional water sports and soaking in the delights of the area, guests can enjoy dynamic amenities like rotating lectures with leading artists and authors; sunrise yoga; and flights of locally crafted wines and beers at The Sand Bar restaurant. Perfect for families and romance, The Lake House on Canandaigua is nostalgic and trend-setting in equal measure.

Related: The 12 Best Lakefront Hotels in the U.S.

On Our Radar: The Maker, Hudson, New York

Created by the co-founders of the beauty brand Fresh, Lev Glazman and Alina Roytberg, along with hospitality expert Damien Janowicz, The Maker celebrates the creativity and history of the artistic Hudson Valley. Located in downtown Hudson, the property features an impressive art collection, as well as furniture and other décor items, from local and global artists and artisans. The 11 rooms are unique and likewise inspired by creatives, in varying degrees evoking the studios of the poets and gentleman scholars of the Georgian Era and the sultry, shadowed salons of La Belle Époque and 1920s Paris. The European-inspired café, glass conservatory restaurant and leather-and-velvet-clad cocktail bar focus on seasonal, local ingredients—and do not disappoint. Plus, when you’re not exploring Hudson’s many delights, you can relax at the courtyard pool, in the Library (curated in partnership with The Strand Book Store), browse the well-curated boutique or find your new scent in the Perfume Library, which has nearly 200 perfumes selected by Lev Glazman. Read more.

Related: Top 10 Trips to Take With Mom

On Our Radar: Inness, the Catskills, New York

Opened in July 2021, Inness is set on 225 acres between the Catskill and Shawangunk mountain ranges, offering a chic country escape that combines classic charm (vintage furniture, woven rugs, wood-burning fireplaces) and contemporary appeal (think: natural wine lists, Aesop bath products, Scandi-minimalist palettes). Guests can choose to stay in one of the 28 freestanding cabins or in the 12-room farmhouse, and shared amenities include a Mediterranean restaurant and outdoor grill (which incorporate local, seasonal produce and ingredients from Inness’ own garden), a nine-hole golf course designed by King Collins Golf, two hardcourt tennis courts, two salt water pools (and a seasonal pool bar), 60 acres of hiking trails and an in-the-works spa and gym facility (slated for fall 2023).

On Our Radar: Wildflower Farms, Auberge Resorts Collection, Gardiner, New York

Just a 90-minute drive from New York City, tucked away amid 140 secluded acres, where the Hudson River Valley meets the foothills of the Catskills, the latest property from Auberge Resorts (The Lodge at Blue SkyMayflower Inn and SpaHotel Jerome and many others), Wildflower Farms opened September 2022, with 65 freestanding cottage-style accommodations, brought to life by architects Electric Bowery and designer Ward and Gray. A plethora of wellness and outdoor activities are on offer, along with a rustic, locally-focused main restaurant, Clay. Guests should be sure to make time for visits to the nearby Mohonk Preserve for hiking and rock climbing, as well as the many distilleries and wineries and art and design galleries of the area. Special experiences on offer include a tasting tour at Tuthilltown Distillery (to experience New York’s First post-Prohibition distillery), a botanical mixology class, flower arranging and pressed-flower pottery-making with local Hudson Valley artists, farm-to-table activities like foraging, exploring the vegetable gardens and orchards (and feeding the resident chickens, and collecting their eggs, every morning), cooking classes, picnics—and, of course, finding peace and reflection among the sprawling fields of wildflowers.

Related: 5 Reasons to Travel to Upstate New York This Fall: New Hotels in Hudson Valley & the Catskills

Indagare Adored: Troutbeck, Hudson Valley, New York

The scenic Hudson Valley has beckoned artists for centuries to reflect and create amid its peaceful woodlands and river valleys—and many Indagare members seek out this destination for these very restorative qualities. Our top property in the region is the manor-turned-hotel Troutbeck, which was formerly owned by the poet-naturalist Myron Benton (a peer of Emerson and Thoreau). Troutbeck is easily reached from New York by a two-hour train or car ride, making it a supremely convenient escape. The 36 guest rooms and suites feature modern and simple décor (including Frette linens, Malin + Goetz products and heated floors in the bathrooms), and the main restaurant’s farm-to-table cuisine follows a similar ethos, highlighting local producers. There are also two tennis courts, a small pool, a space for yoga and Pilates and three trout pools, accessible only to guests. Read more.

Related: 5 Best U.S. Road Trip Ideas

Indagare Adored: Glenmere Mansion, Chester, 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’s Lizzie Eberhart

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 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 a meal 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.

Related: The 31 Best Farm-to-Table Restaurants in the World

Indagare Adored: Miraval Berkshires, Massachusetts

Sister property to Miraval Arizona and Miraval Austin, Miraval Berkshires opened the summer of 2020 in rural Massachusetts to much anticipation. With access to the surrounding area’s spectacular New England scenery, Miraval Berkshires is the iconic wellness brand’s first East Coast property, and it offers all of the things that make Miraval such a leader in the health spa sphere: a serene setting; a “life in balance” philosophy that incorporates eating well, exercising, spending time outdoors and simply having fun; an enormous range of fitness classes and adventure excursions; and a warm and friendly staff. Visitors can expect to see modern, minimalist design schemes that feel fresh, chic and Scandinavian-inspired—thanks to the New York-based firm Clodagh—as well as a fantastic equestrian program, a golf course, an organic farm and the brand’s largest Life in Balance Spa (where you should not miss the Thai-inspired water yoga). Read more.

Related: The Top 10: Prettiest Beaches in America

Indagare Adored: Canyon Ranch Lenox, the Berkshires, Massachusetts

First built around a grand, turn-of-the-century mansion that was a “summer cottage” for a late 19th-/early 20th-century robber baron, the (partially) newly renovated Canyon Ranch in the Berkshires has become an antidote for the busy and stressed in the Northeast, a place to heal, motivate, refresh and refocus. Popular with groups of women and wellness-focused couples who come for a three- or four-day retreat, Canyon Ranch Lenox is a highly goal-oriented spa that focuses as much on fitness and lifestyle as it does on spa treatments, spiritual and holistic healing, Eastern medicine, and medical lab work. It is a year-round destination with plenty to do within the expansive fitness facilities—plus the option to take nature walks and hikes on property and nearby.

Related: What’s New in New York City: Hotels, Restaurants & Culture in Manhattan – Fall 2022

Indagare Adored: The Point, the Adirondacks, New York

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 and cozy fireplaces. 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 fantastic dinner services.

Related: The Reinvention of The Point, The Classic Adirondacks Resort

Indagare Adored: 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.

Related: 13 Ultimate Wilderness Vacations

Indagare Adored: 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 showcases 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. 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.

On Our Radar: Pickering House Inn, Wolfeboro, New Hampshire

Photo courtesy the Pickering House Inn

Photo courtesy the Pickering House Inn

Unlike a Maine or a Cape Cod, New Hampshire has not quite found its spot on the summer-retreat circuit; however, a newly restored inn might change that. Opened in the summer of 2018, Pickering House is located in Wolfeboro, on scenic Lake Winnipesaukee (a two-hour drive from Boston). The property features 10 stylish guest rooms and sitting rooms with fireplaces, and the on-site and nearby activities include cooking classes in the beautifully restored kitchen, as well as hiking and boating in this unexplored corner of New England.

Related: Private Charter Flights: What to Know Now

Indagare Adored: White Barn Inn, Auberge Resorts Collection, Kennebunkport, Maine

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. Read more.

Indagare Adored: Inn at Perry Cabin, St. Michaels, Maryland

Less than a two-hour’s drive from Washington, D.C. or a four-hour drive from Manhattan, The Inn at Perry Cabin is a bayfront escape ideal for a romantic summer getaway to the Mid-Atlantic. The grand 18th-century mansion, lined by linden trees, contains spacious suites done in soothing creams and blues, as well as the locally inspired Stars restaurant and timeless Purser’s pub. There’s also a lovely garden and pool area, which also houses a spa and fitness center. For a true home-away-from-home feel, book the Master Suites, which have terraces from which to enjoy the gorgeous water views, or the one-bedroom suites, which are spread over two levels, offering a spacious layout and plenty of natural light. Read more.

Contact Indagare or your Trip Designer to start planning your summer East Coast vacations—this year and beyond. Our team can provide information on the best hotels and rooms to book, restaurant and shopping recommendations and more.

– Elizabeth Harvey on May 3, 2023



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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