The Mill Houses in Livingston Manor, NY
This collection of five 19th-century homes with charming interiors, plus walk-to-everything ease, can host groups up to thirty people in Livingston Manor, NY.
The Graham & Co. in Phoenicia, NY
This modern motel is take on a classic Catskills getaway. With a blend of vintage character and contemporary comfort, the laid-back Graham & Co. offers a nostalgic nod to the region’s heritage while delivering all the essentials for a stylish and simple escape.
Moon Cabin in Windham, NY
Near both Windham and Hunter Mountains, The Moon Cabin is a thoughtfully designed log home surrounded by forest, hiking trails, and a private pond. One of our lodging picks for Windham, NY, featured in a few of our guides, the rustic-luxe log home surrounded by forest, hiking trails, and a private pond.
Winter in the Catskills: Cozy Mountaintop Rental in Livingston Manor, NY
Perched above the town of Livingston Manor in the Catskills, this cozy two-bedroom home is available as a furnished winter rental from January 1 to May 1, 2026. A perfect winter home base for anyone craving time Upstate, the house is well-suited for remote work, creative ...
The Henderson in Hankins, NY
Victorian grandeur meets Catskills charm at The Henderson in Hankins, NY. 120 miles from NYC, guests are greeted by the soothing sounds of Hankins Creek below the home, plus architectural details of a bygone era. This grand Victorian home was a boutique hotel in the 1860s, and now offered as a unique escape from the city, with a custom stone hot tub, outdoor kitchen and shower, fireplace and more.
Old Quarry House in Catskill, NY
In the woods of Catskill, NY, Old Quarry House offers a unique retreat with a private swimming hole, dual outdoor fire pits and one cozy indoor fireplace. This modern home features oversize windows and glass doors throughout for a sun-drenched getaway — perfect for chilly seasons when brisk weather keeps you indoors. During summer, enjoy the home’s private swimming hole on Kaaterskill Creek: pack a bag and head down to the water, enjoying meals at the designated picnic area with table, grill and bonfire — or to the swimming area, with flat rocks that seem to float above the surrounding water.
Two Good Cabins in Roscoe, NY
Just over two hours from NYC, these lakeside cabins are located on a peaceful, non-motorized lake in the heart of the Catskills. Accommodating up to seven guests in five bedrooms, two cozy cabins offer just the right amount of space and privacy for groups of friends and family.
River Run: a Tennis-Centric Getaway in Cummington, MA
Located in the Berkshire Hills three hours from NYC, the idyllic River Run accommodates up to 12 guests. Just steps from the Westfield River, the sound of the water provides a serene backdrop to an already beautiful landscape, complete with a HarTru clay tennis court, cedar hot tub, and great fishing spots right out the front door.
Rowley House in Eldred, NY
Following an extensive renovation by SOON Architecture Studio, this modern three bedroom cabin with a sauna is filled with treasures from local artisans, designers, and boutique shops. (You may also recognize it in this week's WSJ Real Estate feature on saunas!) From top to bottom, the thee-floor house has tons of space to spread out or get cozy. On its basement level, a lovely bedroom has its own bathroom and is also home to the Rowley House sauna and gym. On the main level, find its expansive kitchen, a living room with a cozy wood stove, and two equally lovely bedrooms that share an additional bathroom. On the third floor, a "snug" loft room has treehouse vibes, and is home to the TV (plus a pull-out sofa for movie nights or sleeping kiddos.)
Moody Pond House in Warren, CT
Less than 100 miles from NYC, find the magical Moody Pond House: a brand new, modern home tucked away on 18.5 acres in the impossibility picturesque Warren, Connecticut. Named after the gorgeous pond on the property, the popular rental home offers a cushy, private retreat year-round.