6 Cape Cod and Hamptons Escapes to Plan From Westchester

Adobe Stock / Chee-Onn Leong

Thinking about a summer trip to Cape Cod or the Hamptons? Consider these easy escapes near Westchester County.

By Andrea Capodilupo, Cristiana Caruso, Maya Ono, Claudia Ossa, and Brooke Bizzell Stachyra

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.

Cape Cod
Cape Cod, Massachusetts. Adobe Stock / Chee-Onn Leong

Baron’s Cove

The Hamptons – Sag Harbor

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.

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The Hamptons Sag Harbor
Located on the water, Baron’s Cove is perfect for boating or just bystanding. Courtesy of Cape Resorts

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

Sag Harbor
Feel like a classic Hamptonite sipping cocktails at this tufted-chair-and-dark-wood-laden bar. Courtesy of Cape Resorts

Red Jacket Beach Resort

Cape Cod – South Yarmouth

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.

Oceanfront Room
Oceanfront Room. Courtesy Red Jacket Beach Resort

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

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Take a break from reality by relaxing on the patio.
Take a break from reality by relaxing on the patio. Photos courtesy of The Roundtree Amagansett

The Roundtree

The Hamptons – Amagansett

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.

The Roundtree The Hamptons
Photo courtesy of The Roundtree, Amagansett

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.

Each suite at The Roundtree feels secluded, homey, and private.
Each suite at The Roundtree feels secluded, homey, and private. Photo courtesy of The Roundtree, Amagansett

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

The Pridwin

The Hamptons – Shelter Island

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.

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The Hamptons Shelter Island
The Pridwin’s cozy cottages make for the ideal getaway. Photo courtesy of Cape Resorts

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.

The Hamptons
The motif is drenched with blues and other nautical touches. Photos courtesy of Cape Resorts

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.

The family-friendly game room is perfect for unwinding after dinner.
The family-friendly game room is perfect for unwinding after dinner. Courtesy of Cape Resorts

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

Ocean Edge Resort & Golf Club

Cape Cod – Brewster

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.

Ocean Edge Beach Bar
Ocean Edge Beach Bar. Courtesy of Ocean Edge Resort & Golf Club

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.

Ocean edge cape cod
From single rooms to villas, Ocean Edge offers accommodations for practically everyone. Courtesy of Ocean Edge Resort Golf Club

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

Bar igloo cape cod
Step inside the Frost Bar Igloos for a beverage with pizzazz. Courtesy of Ocean Edge Resort & Golf Club

Chapter House

Cape Cod – Yarmouth Point

The apotheosis of everything Cape Cod is known for — charm, history, and a warm welcome — can be found beyond the 300-year-old doors in Yarmouth’s latest boutique hotel. Chapter House’s recently renovated 21-room floor plan (split between the Victorian Main House and quaint Carriage House) offers guests rustic touches, like carved four-post beds and original hardwood floors, with such modern flourishes as Le Labo toiletries and newly installed tubs and showers.

Yarmouth Point Cape Cod
Sip on wines and spirits in front of the firepit overlooking the spacious lawn. Photo by Jessica Scranton

Stretching out on two expertly manicured acres, the property is far from the madding tourism crowd. Instead, expect a vacation that challenges you to accept the stillness and exist in the moment. A short walk down the road will produce quintessential Cape Cod cafes and shops, speckled in nautical themes and friendly faces. A 10-minute drive will take visitors to any of the handful of beaches that line the Atlantic.

Owners Phil and Silvia Baxter wanted their guests — no matter if they’re coming from far and wide or just locals escaping for a weekend — to experience an authentic Cape Cod stay. “We want our guests to feel like they’re coming into our house, not just another commercial hotel,” says Phil. With amiable staff who treat you like an old friend (and hand you a glass of sparkling wine upon arrival) and a vibe that encourages conversations with strangers, it takes work to remember that you’re not crashing at a longtime pal’s house.

hotel room
Guest rooms have old-world charm, with chic and renovated amenities. Photo by Jessica Scranton

The Main House boasts a specialty cocktail bar, which serves both inventive and classic takes on bar programs we’ve seen back home (may we humbly recommend the house made margarita). Have a drink on the back patio in front of a crackling firepit during one of the bar’s nightly cocktail hours or just tie a bow on your trip with a night-cap while looking out on the historic King’s Highway.

The moniker “Lodging and Spirits Since 1716” under Chapter House’s marquee isn’t just a cute turn of phrase for patrons. If you’re feeling brave, many staff have claimed to feel the paranormal presence of something beyond the veil in the Carriage House — no holy water needed, as all ghosts are reputedly of the Casper variety. On season rates start at $239/night. —CC

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