Vacation rentals in Chatham

Barn Stay at Shadowbrook Farm

Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored into a beautiful guest house. It sits upon a two hundred acre working pasture raised meat farm. This barn was used to hold, and milk cows for two hundred and fifty years. Guests will have access to portions of the farm lands which are highlighted on the maps provided in the Farm Stay manual. If you follow the farm road, you are able to meet every farm animal on the property!

The Loft at Sweet Pea Farms

The Loft at Sweet Pea Farms is a modern, beautifully appointed apartment with every amenity you could need. Overlooking 140-acres of awe-inspiring farmland, the Loft boasts a huge 1500 sq ft space with one queen bedroom and an additional queen murphy bed in the living area. Enjoy a coffee while taking in views of rolling hills; listen to records while you sip a whisky; or make dinner for your friends & family. Work, unplug, or a little of both in this slice of heaven in the upper Hudson Valley.

The Cottage on Sylvester Street

The Cottage on Sylvester Street welcomes guests looking for a relaxing weekend or longer stay in a small-village setting. Located at the heart of the historic Village of Kinderhook, this stylishly renovated house is located amongst Kinderhook's collection of historic architectural gems. Within easy walking distance are eateries, wine and beer bars, The School I Jack Shainman Gallery, historic sites, the farmers' market plus farm stands, and quiet, scenic roads perfect for walking and cycling.

Guest Suite in Old Chatham Hunt Country

Looking for all the perks of a hotel while staying at a house in the country? This tranquil, light filled room overlooks horse pastures and a dirt road in the heart of Old Chatham hunt country. A private entrance leads to a guest suite which includes a queen size bed, sitting area, kitchenette, and walk-in closet. Located on the first floor of a newly built, net-zero home. Power comes from solar and solar water panels provide for guilt-free hot showers! 50 MBPS fiber optic Internet!

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

The Red House

Welcome to our historic and charming home, tucked away on 50 acres of beautiful, serene woodland. Built in 1840, our 2200 square foot residence combines the authenticity of centuries-old wood beams with cozy, comfortable interiors. The Red House is close to the charming towns of the Hudson Valley: Chatham, Kinderhook, Ghent and Hudson. There is also easy access to Tanglewood, Jacob's Pillow, Mass MOCA, Williamstown and Tannery Pond.

Tiny House, Big Adventure on 70 acres

Welcome to "The Tiny" at The Hemptons in the Hudson Valley. The not-so-tiny house is 400sf with plenty of space to stretch out. Each of the two bedroom lofts have a comfy queen bed on a low profile frame. The kitchen is equipped for basic cooking (read: Not good for Thanksgiving, but perfectly suited for standard cooking endeavors). Regretfully, we are unable to accommodate service animals due to the health risk it poses it the owners.

Winter Cabin Hideaway - Views + Fire Pit + Hot Tub

Escape to your cozy mountain retreat—perfect for winter getaways! Just 15 mins to Jiminy Peak and close to Tanglewood, MASS MoCA & The Clark. Enjoy skiing and nights under the stars in the wood-fired hot tub. Warm up by the Breeo fire pit or inside with radiant floors, cook festive meals, and unwind in total privacy. With EV charging and a peaceful workspace, it’s the perfect spot to celebrate the Holidays and enjoy the winter season.

Pet-friendly. Private. Host leans left. F Trump.

This is a recently renovated 120-year-old house. There are no neighbors in sight. The backyard is a wooded area. There is a stream, fire pit, table, and chairs. The garage has been converted into a game room with ping pong, pool, couches and a bar. Across the road is farmland. It's less than one mile off the Taconic State Parkway exit, and about a half hour to both Catamount and Jimminy Peak (ski resorts). Twenty minutes from Hudson.

The Upstate Cabin: A secluded getaway in the woods

Cozy cabin tucked away in the woods, 2.5 hours north of NYC and 2.5 hours west of Boston - where the Catskills meet the Berkshires. There's hiking in the summer, skiing in the winter, and total peace & quiet year-round. This entire cabin has been hand-lovingly restored and we can't wait to share the space with you. Follow us on Insta at @theupstatecabin to follow our upstate adventures and cabin transformation.

Sugar Shack | Romantic Tiny Home + Hot Tub

Sugar Shack | Romantic Tiny Home + Hot Tub. Escape to this 300 sq ft tiny home with private hot tub and she-shed. A peaceful, romantic getaway in the heart of Chatham—just steps from shops, dining, and theater. Only 2.5 hrs from NYC & Boston. Hike, explore, soak under the stars, or cozy up by the firepit. Thoughtfully designed for privacy, comfort, and indulgence. A blissful upstate NY retreat at @artparkhomes.

Design Lover’s Blue Cabin

Blue Cabin is a cozy, design-forward retreat between the Capital Region and the Berkshires. Enjoy vaulted wood ceilings, a forest-green kitchen, and a spa-style bath. Outside, unwind in the covered lounge with U-shaped sectional, charcoal grill, and TV—or explore the backyard, where a creek runs through and a seasonal flower garden blooms. Peaceful, private, and perfectly located for both rest and adventure.