New York winter: deep breath in.
New York summer: deep breath out.
And we plan to make the most of this season’s collective exhale outside city confines. Air’s just cleaner out there.
Thusly, we present our Summer Rental Guide — a deep dive into the most desirable warm-weather haunts from Montauk to Woodstock.
Please enjoy.
And we’ll see you out there.
The Edgemere Residence
Montauk
Situated directly on the placid shores of Montauk’s Fort Pond, the Edgemere Residence boasts airy, high-ceiling’d spaces, six bedrooms complete with baths, and lawned gardens with a firepit from which to watch gorgeous sunsets over the lake. Oh, and a five-minute walk to the beach.
The Gray Street Guest House
Poughkeepsie, NY
A wonderfully low-key artist’s retreat just north of the city, Gray Street is split into two apartments you can rent separately or together, depending on your needs. Relaxed, airy digs, a great kitchen for cooking and just a couple minutes from the stunning Walkway Over the Hudson.
The Haven’s Beach Residence
Sag Harbor
Polished dark wood floors, elegantly rustic whitewashed walls and a refreshingly minimalist aesthetic — call it “flip flop chic.” Outside: a massive wooden deck overlooking the sprawling frisbee-ready yard and heated pool.
The Maggie Hoag Residence
Delhi, NY
Nestled in the woods outside the Catskills hamlet of Delhi lies a log cabin hideout with eye-popping geometric wooden walls, a wood-burning stove and quite possibly the world’s most perfect whittling porch. Bonus: if you’ve got kids, they’re gonna lose it over the bunk-bed fort.
The Oceanfront Mansion
Westhampton
This is your Weekend at Bernie’s moment. Eight bedrooms. Panoramic views of an ocean so close you’ll be tempted to replace bathing with it, all via your own private boardwalk. Don’t care for Mother Nature’s waters? Stick to the oceanfront pool and jacuzzi.
The Old Farm Residence
Bridgehampton
It may be a farm, but this one’s far from rustic. Handsomely furnished with striking modern art throughout and room for 16+, the Old Farm also boasts gorgeous lawns and a stone-tiled pool complete with Buddha statues reminding you to relax, man. You’re on vacation, after all.
Historic Waterfront Mansion
Port Washington
Built in 1861 on the waterfront of Long Island’s north shore, this historic Victorian home sports charming, old-world decor, paddleboards in the boathouse and a porch swing for enjoying absolutely jaw-dropping sunsets over the water.
The Country Estate
Woodstock, NY
A private, eight-acre property at the base of Ohayo Mountain, this Provencal-style estate has massive, stylish interiors with room for eight, plus a saline pool amidst lush greenery, tennis court and the treehouse your correspondent always dreamed of as a kid.
Rose Hill Estate
Water Mill
Quite simply the most baller summer rental out there. Look at the photos. Handsome stone terraces overlooking a 70-foot beach-entry pool and tennis courts. Sweeping, hound-release-worthy grounds. No less than ten suites, all serviced by a full-time staff. Gym. Basketball court. Massage room. Theater. This is the getaway of the 1%.
The Tinker Street Farmhouse
Woodstock, NY
Stylish and cozy in the land of the Upstate hippies, the Tinker Street Farmhouse is a two-bed, two-bath charmer perfect for a two-couple weekend getaway. Massive stone fireplace, handsomely appointed sleeping quarters and a great patio for enjoying the night air and a bottle of vino.
The Tivoli Barn
Tivoli, NY
Hands down the most stunning property we came across — properly rustic but with a refreshingly refined feel. Perfect for hosting festive communal dinners around either the indoor or outdoor tables, plus a tub boasting a view that’ll keep you in there till you’re properly pruned.
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