It’s no secret to New Yorkers that there is a wealth of culture, nature, and leisure just a few hours outside the city, but it still feels like you’ve gamed the system when you stumble across that perfect rental property and commit to a few days away from the grind. We’ve done the legwork for you here, combing the listings for a few unique properties to kickstart your dream getaway this fall and winter.
It’s hard to beat the appeal of a classic airstream trailer—throw a generous porch with a hot tub into the mix and you’ve got yourself a guaranteed good time. The Airstream is just one of a few lodging options at June Farms, a working farm and event space outside Albany, but it is certainly the one with the most charm. Meticulously renovated with Kohler and Schoolhouse Electric fixtures, the trailer has a bright, open floor-plan complete with a galley kitchen, Casper bed, and sliding glass doors to let in the fresh air. Be sure to pay a visit to the resident animals during your stay: Shire Horses and Highland Cattle—along with pigs, chickens, ducks, and goats—make up the June Farm livestock program, and farm staff are happy to facilitate an introduction.
The recent popularity of Tiny Houses, specifically the secluded woodland variety, speaks to a universal desire to untether ourselves from our homes, devices, and endless zoom meetings, and reclaim a sense of freedom. The Glass House in the Hudson Valley offers such an off-the-grid escape (though there is WiFi, should you choose to connect to it). Situated on a 30-acre farm property near Beacon, The Glass House is just 90 minutes from NYC, but you wouldn’t know it when you’re watching the sunrise over the mountains through panoramic windows on a frosty, late-fall morning. Enjoy an evening around the fire pit, all the creature comforts that can reasonably fit into 180 square feet of living space, and sweet, blissful solitude.
Sleek mid-century style meets laid-back country living in this 1960s bungalow. The Bunkhouse sits on a sprawling property in Saugerties (near Woodstock) that backs up to a tree-covered hillside and small stream; the wildness of the exterior is a perfect foil for the neat modernity inside. For the design-savvy traveler, The Bunkhouse decor is noteworthy in that it’s comprised almost entirely of mid-century antiques and replicas in a tight color palette reminiscent of the era: a forest green settee, mustard yellow accent walls, and a burnt orange Malm fireplace complete the aesthetic. Superhost Hazel hails from Texas, which makes sense when you see the back porch complete with string lights, a charcoal grill, and a dining table that looks straight out of a BBQ joint.
Did your childhood fantasy treehouse include a wood-burning stove, vintage bathtub, writers nook, and multi-level wraparound deck? Let The Treehouse in Hawley, PA bring those fantasies to life. This quirky octagonal home sits on (above?) 9 acres of private woods just a quick drive from Narrowsburg, NY, a sleepy river town with great shopping and dining. Perfect for a couple or a small group gathering, the unique layout offers both open public spaces and cozy private bedrooms, with stellar views to the surrounding woods on all sides. Camp Caitlin, the owners, operates four other properties in the area—if The Treehouse is unavailable for your desired dates, take a look at their other excellent stays.
No Upstate New York travel list would be complete without at least one converted barn; though there are more than a few to choose from, this modern architectural gem in the Catskills is a standout star. Designed by award-winning firm Lang Architecture, The Barn boasts an in-ground Mod Pool made from a shipping container embedded in the cedar deck, and inviting living spaces that celebrate quality materials. Floor-to-ceiling white oak paneling and full-length insulated windows commingle with vaulted ceilings and custom stonework. Nearby attractions include multiple breweries, hiking and swimming in the Mohonk Preserve, and the offbeat college town of New Paltz.