Five Picturesque Rentals
in the
Hudson Valley


Summer at one of these pastoral retreats,
all less than two hours north of New York City.

Morning coffee with mountains in view. An afternoon dip in a secret swimming hole. An Instagram-worthy dinner at a celebrated farm-to-table restaurant. A summer in the country is one you’ll never forget, and that holds especially true in New York’s Hudson Valley. Consider spending yours at one of these rental properties in Dutchess and Columbia counties.

The House: Southfields, a charming four-bedroom house with five full bathrooms and two half-bathrooms spread over almost 5,000 square feet — all set on a pastoral 24 acres. On the first floor, you’ll find the living room with a large stone fireplace; the primary suite, which also has its own fireplace, plus two separate primary bathrooms; an eat-in kitchen with a home office nook; and a bar area. Upstairs, there’s a great room with soaring cathedral ceilings, a game room, and three additional bedrooms, each with its own en suite bathroom. Outside, there’s a screened porch and a heated gunite pool. 

The Place: Considered the equestrian epicenter of Dutchess County, picturesque Millbrook is what many might picture as the quintessential Hudson Valley town. Its charming village teems with antique shops, fashionable boutiques, and exciting eateries, including a classic diner with tabletop jukeboxes. The surrounding area, or “hunt country” as it’s known locally, plays host to top-shelf organic farms that supply the kitchens of the plentiful farm-to-table restaurants nearby, as well as in New York City.

Represented By: Paula Redmond of Corcoran Country Living.

The House: If green acres and farm living is the place for you, kick back and enjoy your summer days relaxing at Cedar Heights Farmhouse, set on eight acres of fields and woods. Originally built in the 1830s, this charming four-bedroom home has been updated with a modern kitchen but otherwise retains its authentic period charm, like the cozy living room with its tin ceiling and fireplace. There are also two home offices, perfect for finally penning the Great American Novel or, more prosaically, taking a team meeting over Zoom. Outside, there’s a bluestone patio, a basketball court, a ping-pong table, a hot tub, and a fire pit.  

The Place: You might be looking for a country escape to get away from it all, but if you ever yearn for a bit of city life, it’s just a five-minute drive to the village of Rhinebeck, which boasts a well-curated arthouse cinema, bookstore, art galleries, a spa, and even a celebrity-owned candy store. From Manhattan, it’s about a 90-minute Amtrak ride up the Hudson to Rhinecliff-Kingston Station, or about a two-hour drive via the Taconic Parkway. 

Represented By: Thea Vengrin of Corcoran Country Living.

The House: It’s summertime and the living is easy at this classic 1850s farmhouse, kitted out with all of the expected modern comforts necessary for a relaxing stay. There are three bedrooms and three-and-a-half bathrooms, a chef’s kitchen, a game room in the basement, a light-filled dining room and living room, a study, and a wraparound porch for sipping a lemonade or two. The bedrooms and bathrooms are spacious, with windows offering views of the surrounding secluded grounds and garden. 

The Place: Staatsburg is a hamlet in Hyde Park and home to River and Post, a popular restaurant serving cocktails, craft beer, and farm-fresh American cuisine. It’s also less than a 10-minute drive to Rhinebeck, with an Amtrak station, or a 20-minute drive south to the Metro-North station in Poughkeepsie. Staatsburg is surrounded by verdant hiking trails and is just across the river from Kingston.

Represented By: Karolina Czekaj of Corcoran Country Living.

The House: A storybook log cabin with three bedrooms and two bathrooms sits on 8.2 acres, overlooking the Webatuck Creek and a waterfall. The primary bedroom has its own fireplace and overlooks the waterfall and the garden. The other bedrooms include one with a queen bed facing the creek and another with two twin sleigh beds that’s accessed by its own staircase. The house, built in 1933, has plenty of room to spread out, including a great room with a fireplace, a sun room, and a soaking tub in its very own room. 

The Place: Set on the eastern border of Dutchess County, Amenia’s landscape has remained remarkably unchanged for centuries, still boasting the gorgeous views that inspired its name, as “amoena” meaning “pleasing to the eye” in Latin. Amenia is home to Silo Ridge Field Club as well as the luxury retreat Troutbeck, which has a popular restaurant on-site, as well as a membership option with access to its pool and tennis courts. It’s also just a short drive over state lines to Sharon and Lakeville, Connecticut, in Litchfield County.

Represented By: Paula Redmond of Corcoran Country Living.

The House: Create a summer to remember in this gorgeous three-bedroom, three-bathroom center-hall Colonial. The designer-decorated house boasts a chef’s kitchen to flex your culinary chops on the locally sourced bounty, along with central air and a sound system. Out back, a porch and stone patio lead down to the heated pool. The scenic property, sequestered by acres of surrounding forest, offers a bucolic landscape of rolling meadows and two ponds. A dog (singular) is permitted, so if Fido has the prerequisite references, they can come along for your summer sojourn.

The Place: LaGrangeville is a hamlet in the town of LaGrange, close to both Poughkeepsie and Millbrook and their great eateries. The house is also minutes away from the Taconic State Parkway.

Represented By: Catherine Howard of Corcoran Country Living.

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