Number of guests: 14
Bed and bath: 7 bedrooms, 8.5 baths
Why we love it: Spacious grounds and interiors, at-home gym, red light studio, hot tub, outdoor movie theater, firepits, games
This nine-acre Sag Harbor estate (near Sagaponack) just might have it all. You’ll be welcomed in by a long driveway, then a koi pond and tennis court, as well as a gradual reveal of the lawn and pool. The outdoor setup is all yours, and it’s extensive: a 55-foot heated infinity-edge pool with a waterfall, a cedar soaking tub for 12, firepits arranged for large groups, and an outdoor movie screen set up across the backyard. There are multiple grilling stations and long tables designed for communal dining. Inside, the house leans more modern-rustic with reclaimed wood floors, antique decor, and a layout built for fun-filled group stays, complete with a media lounge, billiard room, gym, and red light studio—with smart TVs throughout.
City: Sag Harbor
Things to do nearby: Sag Harbor Village, Long Wharf, Havens Beach, Bay Street Theater, Wölffer Estate Vineyard