When Memorial Day hits, and the out-of-office notifications are set, Westchesterites frequently flock either northeast or southeast, where two of the Atlantic Coast’s most popular destinations await. To aid your summer flight to these meccas of leisure time, we’ve brought you the best nests, from bungalows to beachfront suites, that the Hamptons and Cape Cod have to offer.
Sag Harbor, the historical port and whaling village known for its laid-back, artsy vibes and neoclassical architecture, is home to Baron’s Cove. Head through the town, toward the water, and you’ll find the resort tucked in a quiet corner along the shoreline.
This Hamptons hideaway boasts 67 bright guest rooms with modern yet classic nautical furnishings in serene hues that mimic the coastal environment. Choose the standard Village Room, filled with natural light, or upgrade to a Village Garden Room and enjoy a private outdoor area with teak seating and a picnic table. For guests traveling with fur babies, there is a limited number of dog-friendly ground-floor rooms. Baron’s unique “Travels with Charley Dog” package includes a welcome kit containing a dog bed and bowls, disposable waste bags, plus a Frisbee and special VIP (Very Important Pup) souvenir gift.
Arriving guests are not only greeted by spectacular water views but also encouraged to relax via a row of wooden rocking chairs on the porch. The reception area leads to an intimate lounge and bar, where patrons can unwind with a cup of coffee or order a specialty cocktail and light snack. Breakfast is always included, so climb the steps above reception and dine as Hamptonite Truman Capote did decades ago. Have a meal sourced by local purveyors and Long Island specialties at the award-winning Restaurant at Baron’s Cove. The lobster boil is a must-have for any seafood lover, and the menus change often to challenge patrons’ taste buds.
Off-site adventures can start with exploring the town on one of the resort’s complimentary bikes, taking the seasonal shuttle, or driving to the local beach with resort-provided passes. On foot, stroll a few minutes to Main Street and shop the boutiques and specialty stores or browse the various galleries. On season rates begin at $382/night. —BBS
The Red Jacket in South Yarmouth boasts incredible beachfront real estate in idyllic Cape Cod, with 164 rooms and 10 seaside cottages, just under four hours from Westchester County. The well-groomed guests-only beach is just steps outside your door. Set along the Nantucket Sound, every sunset is worth watching from each room’s outdoor space (every room has its own patio or balcony). In the busy summer season, having a private beach in the Cape with parking is truly an enviable asset.
With indoor and outdoor pools, and ping-pong tables and games, there is no shortage of activities for children and families in the sprawling, 95,000-square-foot estate. In the spring and fall, the property’s heated outdoor pool is perfect after a day of golfing. The property is designed with New England Coastal charm, and the on-site restaurant, Clipper Ship Dining Room, serves a hearty breakfast and lunch seven days a week, from 11:30 a.m. to 8 p.m. Under the night sky, the property’s firepit areas are perfect for s’mores and storytelling. The on-site spa has a variety of services, including deep-tissue massages, vitamin C facials, full body scrub treatments, and more. The property offers thoughtful activities for its guests, from yoga on the beach to live entertainment to water activities and even biking on the beach; there is truly something for everyone.
In close walking distance, the Skipper Chowder House is not to be missed, with local fare and the best food in Yarmouth. Intimidated by cracking open a whole lobster? Skipper’s team will teach you how to get the most out of your bright-red delicacy. Yarmouth and Hyannis are quaint drivable towns with tons of cafés, restaurants and local shops. Be sure to check out the JFK Museum after a scrumptious breakfast at the Daily Paper in Hyannis. This seaside escape is sure to leave a lasting memory. Rates start at $159/night. —AC
Step behind the bamboo veil off Amagansett’s Main Street and find your Hamptons home away from home. Each suite feels secluded, with plenty of outdoor space on the property intelligently designed for leisurely activities (think firepits and chic picnic tables) and relaxation (think comfy hammocks and swings). Rooms are equipped with luxury products, like Grown Alchemist, a Nespresso machine to help you get out of bed, and locally made treats.
A quaint breakfast is served daily in the serene garden with pastries, espresso drinks, granola bowls, cereal, and fruit. Around dusk, guests are welcome to The Roundtree at Rosie’s for a complimentary happy hour. A cinematically nostalgic ice cream stand greets guests in the evening, and a short walk down the main gravel path leads to s’mores at the firepits.
Check in with the front office for a beach parking pass, decked out beach chairs, ice coolers, umbrellas, and towels before heading to Atlantic Avenue Beach. Take the 10-minute drive to the ocean or ditch the accoutrements and snag a beach cruiser, also available to all guests. As secluded as The Roundtree feels, it is just steps from Main Street’s greatest hits. Take a short walk to Amagansett Square (154 Main St) for weekend brunch at Wölffer Kitchen (if visiting during off-season, call ahead to check if the restaurant is open) and stop by Cavaniola’s Gourmet on your way back. For a special treat, head to Nick & Toni’s in East Hampton (136 N Main St), about 15 minutes from the property. Pro tip: You will want to order the butternut squash agnolotti.
Bring your favorite canine along (up to two per room!), and they will be met with a dog bed, treats, a doggy towel, water bowls, and lots of love. (A $50-per-night pet fee applies). Rooms start from $495 in the off-season and $695 in the summer months. —MO
If the Hamptons is considered the playground for the rich and famous, then The Pridwin is its offshore summer-camp annex on neighboring Shelter Island. Think along the lines of a chic and modernized beach resort that retains its charm and whimsy. The classic, all-wood resort has been serving visitors since 1927 and recently went through an extensive two-year renovation before reopening in July of 2022. The new interior is modern with touches of nostalgia, kept alive by displaying original memorabilia, like the old guestroom keys, to decorate the reception area.
The Pridwin’s seven-acre property overlooking Crescent Beach has 33 rooms in the main building and 16 freestanding cottages. Amenities at The Pridwin are plentiful, and guests start off a day of beaching and boating with a complimentary continental breakfast served on The Terrace. For some rejuvenation after a day in the sun, the new Pridwin Spa offers a menu of services, including therapeutic massages using healing essential oils and both restorative face and body treatments.
If an adventure is on the docket, bikes are available to explore the island, and the concierge can arrange guided tours and book boating and yachting charters that leave from the resort’s dock. Kayaks and paddleboards are accessible for watersports.
Catch a signature Hamptons sunset dining at The Terrace, The Pridwin’s restaurant boasting Riviera-like views. The atmosphere is sophisticated yet casual, offering both indoor and outdoor seating and making it ideal for special occasions or a meal with the kids. Their menu offers choices to please all palates and features traditional American dishes using locally sourced ingredients. The adjacent circular Crescent Bar offers seasonal bespoke cocktails, and the lounge area in front of the massive fireplace is perfect for listening to live entertainment in the evenings. Rates begin at $191/night off season and $359/night post Memorial Day. —BBS
Longtime visitors to Brewster, MA, aka the inner elbow of Cape Cod, would like it to remain a well-kept secret. But when you experience a place that is the perfect balance of history, breathtaking vistas, and comfortable luxury, all tied up in a bow of year-round good times, word is bound to get out.
A fixture in the chronicles of Brewster, the 429-acre Ocean Edge Resort & Golf Club has experienced many seasons of change on the Cape. The estate’s original mansion was built by a descendant of Cape Cod’s Puritan settlers, Samuel Mayo Nickerson, for his family in 1890. After the home was destroyed in 1906, his widow, Addie, began construction of a new residence, completed in 1912. After a few changes of hands, the property was purchased in the 1980s by a developer with a vision who opened the resort in 1986.
The all-season resort offers more than respite from your workday: Cape Cod’s only Nicklaus Design golf course, five beautiful pools (two of which are indoors), a full-service spa, yoga, beaches, oyster flats, kayaking, paddle-boarding, bike rentals, tennis, live music, a world-class restaurant, a pub, summer and winter bars, igloos, and pickleball. Each room is thoughtfully appointed and spacious, with options ranging from two queen-size beds to updated villas. The Ocean Edge pays homage to “local” by offering cranberry bog tours, art-centric packages in collaboration with the Cape Cod Museum of Art. Surrounded by what Travel + Leisure ranked third on America’s Most Beautiful Coastal Views list, let the soft sand and gentle waves wash your worries out to the Atlantic.
Rates start at $305/night. —CO