19 Charming Airbnbs Near New York City That Are Perfect for a Weekend Road Trip
"Hearst Magazines and Yahoo may earn commission or revenue on some items through these links."
New York City is a road tripper’s 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 from 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
Sleeps: 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 woods, meaning minimal light pollution and maximal stargazing opportunities around the fire pit.
Charming Loft
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
Sleeps: 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.
Cozy Converted Schoolhouse
Location: Shaftsbury, Vermont
Sleeps: 6
Rate: From $323 per night
This recently renovated historic schoolhouse in southwestern Vermont overlooks the owners’ fourth-generation organic farm and the Green Mountains in the distance. Despite the rustic surroundings, the place abounds with creature comforts, including a hot tub and an outdoor shower, while interiors are filled with tactile pleasures like plush sheepskins and hooded robes to wear on your way out to the barrel sauna during wintry New England nights.
RELATED: The Best Airbnbs in New York City With Hot Tubs
Cute Beach Cottage
Location: Lower Township, New Jersey
Sleeps: 4
Rate: From $291 per night
Discard any outdated notions you might have about the Jersey Shore: The Octopus Cottage is set behind a lavender-filled, English-inspired garden in a quiet slice of Cape May County, where horseshoe crabs and migratory birds outnumber rowdy revelers. Inside, the restored 1940s Millman cottage’s namesake mollusk shows up on cheerful fabric cushions and fun-loving wall art, while a pair of pink flamingos stand guard over the outdoor hot tub. Take advantage of the trio of kayaks (two solo and one tandem) to explore the shallow waters of nearby Delaware Bay.
Serene Beach Condo
Location: Rehoboth Beach, Delaware
Sleeps: 4
Rate: From $415 per night
Eschewing any signs of beachside kitsch, this mid-century-inspired condo on the Delaware Shore is a calming respite from the energy of the boardwalk outside, with dark-wood furnishings, neutral tones and tactile natural materials. Owner Juan works in the architecture and interior design industry, so it’s not hard to see why he’s so good at maximizing compact spaces: Take, for instance, the queen Murphy beds which fold up into the wooden slat walls like magic, or the comfortably appointed balcony, with its cushioned sectional and egg chair.
Rural Cottage Retreat
Location: Putney, Vermont
Sleeps: 3
Rate: From $204 per night
Surrounded by a six-acre farm, this wellness-minded Vermont homestead is designed to get you back in touch with nature, from the moon phase wall hanging above the bed to the garden outside, bursting with medicinal plants and vegetables. You could stroll the restorative grounds and the surrounding pastures — where you’ll probably be greeted by the owners’ two dogs — or spend your time in the cozy cushioned reading nook next to the wood-burning stove. If you’re traveling with a larger group or another couple, the owners also rent out a four-season yurt, complete with a deck and outdoor shower.
Quaint Historic Apartment
Location: Lewes, Delaware
Sleeps: 2
Rate: From $245 per night
Nicknamed “the first town in the first state,” Lewes boasts a compact national historic district with buildings dating back to the 17th century. Right in the thrumming center, on Second Street, sits the Rodney House, the former residence of Henry Fisher Rodney, who owned a store here in the 1800s and whose daughter ran a private school onsite. Inside, beamed ceilings from the 1700s still stand above smart modern furnishings, including a dedicated workspace that’s ideal for digital nomads. (Just take note, the owners say this is not a child-friendly space.)
Sculptor-Designed Tiny House
Location: Pownal, Vermont
Sleeps: 2
Rate: From $259 per night
Few Airbnbs are as architecturally intriguing as the Owl Hill House in Vermont, which was designed by a group of sculptors in the early 1980s and looks a bit like a sinuous, surprisingly light-filled cave dwelling — all hand-plastered walls, undulating curves and built-in custom furnishings. Set in the rural southwestern corner of the Green Mountain State, the property is ideally situated for art lovers coming to explore nearby galleries and museums like the Clark Art Institute and MASS MoCA.
Stylish Connecticut Chalet
Location: Southington, Connecticut
Sleeps: 6
Rate: From $269 per night
Hand-built by the current owners’ grandparents in the 1960s, this open floor plan chalet in Connecticut's Hartford County is flooded with natural light from the all-glass back wall, which looks out toward five acres of woodlands that are often visited by bears, foxes, coyotes and bobcats. The design skews mid-century with honey-colored wood paneling, angular furnishings and a thoughtfully curated collection of art books.
Storybook-Style Treehouse
Location: Lee, Massachusetts
Sleeps: 4
Rate: From $275 per night
There’s a fairytale-like whimsy to the turreted, wood-clad Gingerbread House Tower in the Berkshires, which includes a canopy bed, barn doors and folksy macrame wall hangings. It can be found on the grounds of Santarella Gardens, the historic estate of English-American sculptor Henry Hudson Kitson in the Tyringham Valley. New owners Josh and Shaun bought the place in 2020 and have since been lovingly restoring the property, which also includes the one-bedroom Enchanted Tiny Tower and the 18th-century colonial farmhouse Kitson once called home.
Scandinavian Cabin in the Woods
Location: Easton, Connecticut
Sleeps: 4
Rate: From $385 per night
There’s a streamlined serenity to this Scandi-chic Connecticut retreat, with a muted palette of mossy greens and blonde woods and low-slung furnishings that might look at home in an Ingmar Bergman film. Especially hygge-inducing is the second bedroom upstairs, tucked up under the gables in a custom-built wooden alcove, while a hammock and Adirondack chairs around the fire pit make for a great place to try the Swedish custom of fika, or a mid-day pause for a snack and a hot drink.
Mid-Century Modern Getaway
Location: Wernersville, Pennsylvania
Sleeps: 4
Rate: From $229 per night
This unique mid-century modern house straddles a mountain stream in Berks County, which makes it feel a bit like a cross between a Frank Lloyd Wright creation and a covered bridge. From here, you’ll be a close drive to the quaint towns of Pennsylvania Dutch Country and a surprisingly robust wine trail; pick up a few bottles and enjoy them in the property’s hot tub, from where you can hear the burbling creek at night or birdsong during the day.
Unique Dome House
Location: Roxbury, New York
Sleeps: 10
Rate: From $630 per night
Designed by architect Seymour Rutkin in the ‘90s, the Shell House is a half-dome-shaped retreat in the Catskills that looks a bit like a glass-fronted modernist bandshell. Recently, the owners called on the DAAM design firm to spruce up the place, and their elegant refresh incorporates warm oak cabinetry, fluted walls, white quartz countertops and geometric ceramic tiles that play off the shape of the house. Out on the patio, you can enjoy majestic mountain views and a cozy fire pit.
Modern Mountain Watchtower
Location: Catskill, New York
Sleeps: 4
Rate: from $418 per night
Inspired by the concept of a modern watchtower, the Hudson Lookout is an angular house atop Potic Mountain that's all about verticality, with a stylish, black-steel staircase connecting its three floors. Windows of various sizes — above the deep soaking tub, spanning the wall between the leather lounge chairs and Floyd sofa in the living room — frame carefully selected vistas of the Catskills outside. Start your morning by sipping a steaming cup of joe on the roof for the best views in (or atop) the house, then head down to the second floor to relax in the sauna.
Chic Renovated Barn
Location: Essex, Connecticut
Sleeps: 4
Rate: From $398 per night
There’s a rustic austerity to the exteriors of this historic post-and-beam barn in Connecticut, but don’t expect American Gothic when you walk through the front door, which is guarded by a cute, whale-shaped door knocker. Inside, you’ll find amenities both high tech (a Samsung Frame TV, Marshall speakers) and low (an acoustic guitar, a vinyl record collection heavy on the oldies), with thoughtful touches like P.F. Candle Co. room sprays and reed diffusers, Meraki toiletries and locally roasted coffee from Deep River Roasters.
Sunny Family Cottage
Location: Montauk, New York
Sleeps: 6
Rate: From $1,220 per night
Owners Steffen and Sara decamped to this easternmost stretch of Long Island to start their interior design firm, Studio MTK, and you can see their breezy, beachy style in this light-filled, three-bedroom house. Located in a quiet corner of Montauk's Shepherd's Neck neighborhood near Fort Pond, the Tudor-inspired cottage features a vaguely nautical decor, with thoughtful touches like a model sailboat and a ship wheel mirror, contrasting its handmade furniture and abundant potted greenery.
Historic Stone Church
Location: Lanesborough, Massachusetts
Sleeps: 2
Rate: From $395 per night
Located in the Berkshires five minutes from the entrance to Mount Greylock, Massachusetts’s tallest peak, Hinterland Hall started life in 1836 as St. Luke’s Episcopal Parish, and the current owners have been bringing it back to its former glory since buying the place in 2021. These days, the interiors contain many original elements, including two stained glass windows from 1851, 37-foot cathedral ceilings, wide-plank pine flooring and a 161-year-old hand-pumped organ that still plays. Newer amenities include the whiskey-stocked brass bar cart, the HD film projector, the concrete soaking tub and hand-block-printed linen bedding.
Homespun Woodland Hideaway
Location: East Hampton, New York
Sleeps: 3
Rate: From $400 per night
You Might Also Like
