Luxury Vacation Rentals for Families in Hillsdale

Plan an effortless escape with Wander’s luxury family vacation rentals in Hillsdale, New York. Each home pairs the polish of a five-star stay with the warmth of a private countryside retreat, set among rolling hills and big-sky views near the Berkshires.

Thoughtful layouts give everyone room to spread out, with multiple bedroom suites, bunk spaces for kids, and generous great rooms for time together. Expect hotel-grade amenities like ultra fast WiFi, private pools or hot tubs, stocked kitchens, and dedicated work nooks, plus pristine cleaning and 24/7 concierge support. From sunrise coffee on a wraparound deck to a movie night in the media lounge, your family can settle in with ease.

Hillsdale blends Hudson Valley scenery with Berkshires energy. Families can shift from peaceful country lanes to alpine thrills at Catamount Mountain Resort, with ski runs in winter and a tree-lined adventure park when the snow melts.

Ride the Harlem Valley Rail Trail, wander Taconic State Park’s clear streams, or hop to Bash Bish Falls across the border. Copake Lake and Roeliff Jansen Park offer room to roam on water and meadow. With radiant sunsets and starry nights, it is an easy place to slow down together. That is why Wander’s luxury family vacation rentals in Hillsdale, New York are the perfect choice, whether you are traveling for work or leisure.