COURTESY OF THE AIRBNB PHOTOGRAPHER COMMUNITY
New York City is a road-trippers dream hub. Few other metropolitan areas in the United States offer as diverse an array of weekend travel options within a roughly three-hour drive. To wit, you can head out after work on a Friday evening and be in a cabin in the Catskills, a boardwalk on the Jersey Shore, a surf town on the tip of Long Island, a farm in Vermont, or some historic New England hamlet in time for a late dinner.
We’ve collected well over a dozen unique Airbnb locations that push the envelope in terms of design and architectural inspiration, including a tiny house created by sculptors and a restored stone church dating back to the 1830s. All are roughly located within a three-hour drive of NYC and all are run by Airbnb Superhosts with a rating of 4.8 or above. Whether you’re planning a girlfriend getaway, a family vacation, or a solo retreat to work in a form home-away-from-home, these short-term rentals are bursting with character, thoughtful decor, and relaxing amenities.
Looking for more travel inspiration? Good Housekeeping’s 2023 Family Travel Awards covers everything from the best destinations to top-tested gear that’ll help get you there and back with no issues.
Mid-Century Glass Octagon
- Location: Otis, Massachusetts
- Periods of sleep: 4
- Rate: From $317 per night
Encircled by floor-to-ceiling windows, this octagonal house — which looks a bit like a wood-shingled version of those Moka pots you use to make stovetop espressos — offers a front-row seat to the natural wonders of the Berkshires outside, and the forest creeps inside in subtle ways like the feathers and antlers artfully strewn atop the modernist furnishings. The house is surrounded by seven acres of wood, meaning minimal light pollution and maximal stargazing opportunities around the fire pit.
- Location: New Haven, Connecticut
- Sleeps: 2
- Rate: From $156 per night
Taking its name and design inspiration from New Haven’s history as an oyster port, the Pearl is a beautifully appointed loft inside an 1892 Queen Anne-style house two minutes from the Quinnipiac River. Expect bay windows, hardwood floors, and a thoughtful kitchenette, with a refrigerator, tea kettle, coffee maker, toaster oven, and more — though the best seat in the house is the clawfoot tub which is flanked by a row of greenery and sits under a tulip-shaped light fixture you’ll want to take home.
Secluded Modern Cabin
- Location: Phillipsport, New York
- Periods of sleep: 6
- Rate: From $625 per night
Brooklyn-based architect Kyle Page built this cabin as an upstate retreat for his family, and its weathered steel walls and blackened cedar siding provide a moody counterpoint to the greenery of the surrounding 19 acres. He turned to these Sullivan County forests for maple and ash wood, which he transformed into headboards, benches, tables, and stools for the home, some of which feature naturally decorative squiggles created by the (tree-destroying) emerald ash borer beetle. more news