Sensational Summer Rentals in the Hamptons and the Hudson Valley


Whether you’re wooed by the waves or the woods, don’t miss your chance at these seasonal retreats.

A problem with vacations is that, eventually, they end. While these stellar summer rentals aren’t forever, they do offer the promise of a home-away-from-home to escape the everyday hustle and maximize the longest—and hottest—days of the year.

From the sandy beaches of Long Island’s East End to the towering peaks of the Catskills, here’s just a sampling of the rental opportunities available across the Corcoran network in destination towns within a few hours of New York City.

East End

The House: With celebrity provenance and a write-up in Architectural Digest to its name, this fetching farmhouse, hidden away on eight woodland acres in Sag Harbor, is what vision boards are made of. Five bedrooms and four baths are spread over three dazzling floors, with warm natural light meeting you every step along the way. Feel one with nature your entire stay, from marveling at the property as you travel the long driveway to tranquil afternoons spent poolside to peaceful evenings by the screen porch fireplace.

The Place: Historic downtown Sag Harbor is far enough away that home feels like a haven, yet close enough for when you want to experience the singular coastal village. Things feel lovingly stuck-in-time, among the salty old Long Wharf and sea captain’s cottages. Still, ample shoreline, delicious food, and a true sense of community make Sag Harbor shine all summer long.

Represented By: Kial Ramirez of Corcoran’s Southampton Office.

The House: This five-bedroom, net-zero home is thoroughly modern in design and execution. Geothermal heating and solar energy implementation allow you to reduce your renter’s footprint without trading an iota of luxury or comfort. Sleek architecture gives way to an inviting interior, an open plan open to possibilities. Enter into a double-height foyer and be immediately drawn to the living-dining-kitchen area, complete with a gas fireplace, space for entertaining (or intimate dinners), and top-of-the-line appliances.

The Place: A summer spent here is a summer nestled in the serene hamlet of Northwest Harbor, located north of the highway in East Hampton along Gardiners Bay. Over 600 acres of pristine nature—ideal for birding, hiking, picnicking, and more—are a short trek away at Cedar Point County Park, and you’ll still be a short drive from the East Hampton village scene.

Represented By: Randi R. Ball of Corcoran’s East Hampton Office.

The House: An idyllic Shelter Island property, set so close to the edge of Gardiners Bay that the infinity-edge pool practically cascades into it. Two residences compose the property, dazzling at every turn. Walls of glass are found throughout the Ranch-style main house, unveiling sweeping panoramas over the bay that stretch as far as Orient Point. Vaulted ceilings and exposed beams in the living and dining rooms—not to mention the wood-paneled primary bedroom—lend an aura of rustic grandness. A two-floor guest house is perfect for anyone who wants to join the vacation, replete with an oversized living area and a spa-like bath.

The Place: You could enjoy a summer on Long Island, but why not take things one step further? Shelter Island floats between the East End’s twin forks and blends the lifestyles of both. Explore nature, hobnob at a marina, indulge in freshly-caught seafood, and still be home in time for a back patio barbecue at sunset. Shelter Island is as enchanting a locale as you’ll find this summer.

Represented By: Peter M. McCracken of Corcoran’s Shelter Island Office and Patricia Han of Corcoran’s Southampton Office.

The House: All the trappings of a glorious Southampton home, with magnificent blasts of color and flair within. Inside or out, you’ll be living your best life. There’s an eclectic mix of traditional and bold design around the home, the latter found in rooms such as the hot pink parlor or furniture like the floral pattern bench seating in the kitchen and dining room. Out back, enjoy the fresh air from atop the deck or the porch it provides cover for. There’s also a sparkling swimming pool, plus a jungle gym for the kids or the young at heart.

The Place: To some, Southampton is the cream of the Hamptons crop and it’s hard to argue with them. For an out east summer experience that feels true to what we think of when we imagine “the Hamptons,” look no further. This four-bed home is near some cherished coastline and beaches, terrific restaurants and shops, history and culture, and—of course—golf.

Represented By: Beth E. Marano of Corcoran’s Southampton Office.

Hudson Valley

The House: Unwind in the heart of the historic Hudson Valley at this beautifully decorated three-bedroom, three-bathroom Colonial, boasting a chef’s kitchen, central air, and best of all, a gorgeous heated pool. Set down a gravel drive, the picturesque main house overlooks two ponds and a classic red barn, and it’s all surrounded by meadows and forestsa true country oasis that’s just an hour-and-a-half from New York City, with the Taconic Parkway mere minutes away.

The Place: Lagrangeville is a quick drive to picturesque Millbrook, where you’ll find the gorgeous Innisfree Garden, great antique shopping, excellent restaurants, and a beloved local bookstore-toy store. This is also horse country—and wine country—so if you’re interested in riding lessons or touring wineries (or both), there are plenty of equestrian farms and vineyards to visit. 

Represented By: Catherine Howard of Corcoran Country Living.

The House: You’ll find unparalleled solace at this four-bedroom, three-and-a-half-bath farmhouse, situated on 65.37 private acres just two hours north of Manhattan. Relax in serene seclusion, surrounded by sweeping views of the Berkshire Mountains from all sides, with beautiful vistas from sunrise to sunset. The house has central air, heated slate floors, top-of-the-line appliances, and an 18-foot beamed ceiling in the great room. There’s also a 60 x 20-foot pool, a fire pit, a stone patio, and wildflower fields. Plus, there’s a pool cabana that’s connected to the property’s high-speed internet, which can be used as a home office between laps.

The Place: For a sleepy town of rolling hills and dairy farms, Ancram is loaded with culture. The Ancram Opera House offers live theater all summer long. A short drive to Millerton or Hudson will bring you to all the shopping and dining you might desire, with choices that rival the city’s best. Alternatively, it’s about a half hour drive to the Massachusetts or Connecticut side of the Berkshires.

Represented By: Karolina Czekaj and Paula Redmond of Corcoran Country Living.

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