For residents of New York City, virtually any minor inconvenience serves as an immediate justification for a weekend trip Upstate. Whether it is a clanging apartment radiator aggressively blasting dry heat while the autumn weather remains mild outside, an exhausting workweek spent chained to an overwhelming inbox, or simply catching the very first glimpse of a reddening leaf in a local park, the seasonal call of the mountains and valleys is difficult to ignore.
With most small towns located within a comfortable two-to-three-hour drive of the city—and several accessible directly via commuter train lines for those traveling without a car—escapes to Upstate New York require very little excuse. While the Hudson Valley and the Catskills are heavily dotted with sophisticated boutique hotels, travelers seeking true relaxation and a more personalized domestic experience often turn to private rentals. To help travelers navigate the vast array of options, lifestyle publication Vogue has curated a comprehensive guide highlighting the 22 best Airbnbs across Upstate New York.
This time of year centers heavily on outdoor exploration. Visitors routinely spend their days hiking along rugged mountain trails and babbling creeks, exploring local farmers markets to sample fresh seasonal produce and artisanal baked goods, or dropping by regional breweries in the evening to enjoy a glass of cider under festive outdoor lights. As temperatures continue to cool, the region’s appeal shifts toward evening campfires, pumpkin and apple harvesting at local orchards, and leisurely foliage-viewing drives. Many of these standout properties are situated directly in or within easy walking distance of historically charming towns like Hudson and Woodstock, while others offer deeply secluded, off-the-grid experiences surrounded entirely by open meadows and dense forests.
Inez’s Farm House, Bloomville
Set on 25 acres of rolling meadows and forest land featuring two private streams and a waterfall, this newly renovated 1890s-era farmhouse in the Western Catskills offers travelers a notably slower pace of life. While the residence has been thoroughly updated with modern conveniences such as high-end kitchen appliances, retained details like reclaimed wood and a traditional bread-baking wood stove establish a deeply cozy atmosphere. The main level centers on an expansive open-plan room connecting an eight-person dining table directly to the kitchen. Upstairs, guests can utilize a striking claw-foot bathtub. The property sleeps five across three bedrooms and two-and-a-half bathrooms, sitting approximately three hours by car from New York City.
Edgewood Catskills, Lanesville
Positioned as a boutique nature retreat rather than a traditional house, this intimate rental functions essentially as an upscale adult treehouse. Sleeping two guests with a king-sized bed, the secluded structure offers hot outdoor showers and deliberately lacks both cell service and electricity, providing a genuine off-the-grid experience immersed in the surrounding forest canopy. Despite its deep seclusion, the property sits only a ten-minute drive from the town of Phoenicia and its popular local diner. It is located two and a half hours by car from Manhattan.
Panoramic Lakeviews and Lush Garden, Greenwood Lake
Bordering New Jersey just roughly an hour outside the city, this lakeside property offers a sunlit departure from the heavy wooden cabins typical of the region. The exterior features a private garden complete with a waterfall, a lily pond, and direct views of Greenwood Lake. Guests have convenient access to local wineries, antique stores, and hiking paths, including a trail connecting directly to the Appalachian Trail just a five-minute walk away. The home accommodates four guests across two bedrooms and one-and-a-half bathrooms.
Rustic Designer Space, Hudson
Located directly in the historic heart of Hudson, this light-filled apartment blends modern structural updates with vintage touches honoring the building’s historical roots. The kitchen stands out with decorative tiles and an antique stove, while daily routines are supported by a dedicated coffee and tea station. Accommodating two guests across two bedrooms and one bathroom, the property sits a two-hour drive from New York City and places visitors within walking distance of local boutiques and dining.
Catskills Mill House No 1, Livingston Manor
Designed in a stripped-back Scandinavian aesthetic, this newly renovated farmhouse in Livingston Manor offers an intentionally minimalist retreat featuring antique furnishings and original wood floors. With no television and limited modern amenities, the property caters directly to travelers seeking a complete digital detox. A bunk room accommodates younger travelers, while the hamlet’s coffee shops and concept stores remain within comfortable walking distance. The house sleeps five across two bedrooms and one bathroom, approximately two hours by car from the city.
Cool Cozy Cabin by the Lake, Athens
Embodying the classic A-frame lake cottage archetype, this property features extensive wood interiors, a wood-burning fireplace, a fire pit, and an outdoor grilling deck alongside modern conveniences like a high-end espresso machine. Sleepy Hollow Lake is accessible via a short ten-minute walk in warmer months, while the ski slopes of Hunter Mountain sit a 45-minute drive away. The cabin accommodates six guests across three bedrooms and one bathroom, roughly two and a half hours away by car.
Charming Village Base, Cold Spring
Ideal for travelers without a car, this one-bedroom, one-bathroom village residence sits directly in Cold Spring and is easily accessible from Manhattan via the Metro-North railroad. The minimalist interior features a functional fireplace and a spacious dining table that doubles as a remote workspace. Local coffee shops and hiking paths are located within a brief 15-minute walk, allowing visitors to experience the village entirely on foot.
Moritz Cabin, Hunter
Inspired by traditional Swiss Alpine architecture, this compact, minimalist cabin in Hunter utilizes oversized windows to frame mountain views from a covered outdoor patio. Designed for solo travelers or couples, the interior features a vibrant kitchen, a shower skylight, and a pellet stove. The property is located approximately three hours from New York City by train and includes modern additions like an electric vehicle charger.
The Tower House, Woodstock
Constructed during the 1980s by a master stonemason, this distinctive tower structure in the Catskills features vaulted ceilings and wraparound windows offering panoramic valley views. A second-floor bathtub is strategically positioned to overlook the landscape, while the property’s exterior includes a hot tub and an expansive deck. Located a seven-minute drive from the center of Woodstock, the home sleeps four across two bedrooms and two-and-a-half bathrooms.
The Greenhouse, Tannersville
Dating back to 1971, this A-frame cabin in Tannersville combines mid-century nostalgic charm with an abundance of indoor house plants. While the interior provides a serene gathering space with a record player and board games, much of the time is spent on the outdoor deck equipped with a barbecue grill and string lighting. The property accommodates six guests across three bedrooms and two bathrooms, sitting two hours north of Manhattan by car.
Luxury A-Frame Cabin, Saugerties
Located just ten minutes from Woodstock, this updated A-frame cabin balances rustic appeal with contemporary comforts, including Casper mattresses and a high-end espresso machine. Outdoor amenities feature a cedar wood-fired hot tub, a traditional sauna, a fire pit, and a hammock. The residence accommodates four guests across two bedrooms and two bathrooms within a two-hour drive from the city.
Olive Outpost, Olivebridge
Featuring wood-paneled A-frame ceilings, forest green interior tones, and artisanal bathroom tiling, this Olivebridge property provides a visually inspiring retreat. Conveniently positioned for short drives to the Ashokan Reservoir, Kingston, and Woodstock, the home features a sprawling front deck oriented toward the surrounding forest canopy. It accommodates up to three guests in one bedroom and one bathroom.
Hudson Valley Hygge House, Rosendale
Situated on the outskirts of Kingston, this peaceful rental offers multiple outdoor relaxation zones, including a fire pit surrounded by Adirondack chairs, a tranquil pond paired with a hammock, and a screened porch off the kitchen. The interior incorporates natural light, exposed brick, and an indoor fireplace. The property sleeps four across two bedrooms and two-and-a-half bathrooms, located an hour and a half from New York City by car.
Brushland’s Owl Nest, Bovina Center
Perched atop Bramley Mountain near Bovina Center, this atmospheric cabin features cathedral ceilings, an open floor plan, a wood-burning stove, and extensive wood paneling. The surrounding trees transform into vibrant shades of red and orange during the autumn months. The home accommodates four guests across two bedrooms and one bathroom, sitting approximately three hours away by car.
Away Upstate, Saugerties
Tailored for travelers interested in exploring regional shops and restaurants across multiple small towns, this Saugerties Airbnb provides easy access to Woodstock, Saugerties, and Kingston. The interior features mid-century modern decor and an indoor fireplace, while the backyard offers a pre-stocked fire pit and barbecue grill. The property sleeps six across two bedrooms and one bathroom.
Ranch in the Woods, Warwick
Leaning into Wabi-Sabi design principles, this Warwick Valley ranch home utilizes natural materials and soft lighting to create a serene environment. Guests can begin their days with yoga sessions in a dedicated meditation room known as The Shed, complemented by complimentary locally roasted coffee provided by the hosts. The property accommodates two guests across one bedroom and one bathroom, located an hour and a half from the city.
WabiSabi Tiny Cabin, Walton
Occupying 400 square feet on a wooded hill in the Catskills, this petite sanctuary overlooks stream-fed ponds and a wildflower meadow. The interior centers on an open floor plan with a spiral staircase, natural textures, and a pellet stove, while the exterior provides a fire pit and string lighting. The cabin sleeps three guests across one bedroom and one bathroom, roughly two and a half hours by car from Manhattan.
Fox Ridge Chalet, Margaretville
Subverting the conventional dark log cabin aesthetic, this whitewashed chalet in Margaretville features bright, expansive interiors and an eclectic collection of vintage furnishings. Situated on seven private acres, the property offers numerous indoor entertainment options, including a movie screening projector, a pool table, an exercise bike, and a hot tub. The chalet accommodates up to eight guests across three bedrooms and two bathrooms.
Historic Vanderbilt Estate Carriage House, Hyde Park
Recognized on the National Register of Historic Places, this Hyde Park residence known as "The Gatehouse" was restored in 2016 to incorporate modern comforts while retaining its historical French architecture. Overlooking the Catskills and the Hudson River, the property features a storybook front porch and a separate carriage house with a covered outdoor dining area. It sleeps six guests across three bedrooms and two bathrooms within an hour and a half drive from New York City.
Pond House, Woodstock
Formerly the art studio of social realist painter Reginald Marsh, this restored Woodstock home combines country elegance with artistic history. Floor-to-ceiling windows integrated into wood paneling offer unobstructed views of the estate’s pond directly from the primary bedroom. The property accommodates five guests across two bedrooms and one-and-a-half bathrooms, located two hours from Manhattan by car.
Glasco House, Woodstock
Designed for large gatherings and group events, this converted barn sits on 16 private acres near Woodstock village and can accommodate upwards of 16 guests. The interior features 30-foot ceilings, a grand central fireplace, five-and-a-half bedrooms, and three bathrooms. The rental includes access to a 24-hour digital concierge and optional private chef services.
French-Inspired Maison, Hudson
Serving as a sister property to earlier Hudson designs by New York firm Zio & Sons, this three-bedroom townhouse sits near the main commercial stretch of the Hudson Valley. The interior is rich in historic details, including salvaged library doors, an 1840s mantelpiece, a cast-iron bathtub, and tiled kitchen surfaces lined with copper pans. The home accommodates five guests across three bedrooms and one bathroom, accessible within two hours from New York City by car and train.