Holiday houses in Old Chatham

Stylish Hawthorne Valley Farmhouse Retreat

Hawthorne is a renovated 1920s farmhouse set on 11 acres of pastoral fields, forest and pond, featuring stylish, comfortable, art-filled white and green rooms. Take in the view from the sun porch, nap on the big L-shaped sofa, share cocktails in the field overlooking the valley, and cozy up by the fieldstone fireplace at night. A fully equipped house, with Watson Kennedy goods throughout. Professional design, high quality kitchen equipment and accoutrement, linens, blankets and comforters, with Malin+Goetz & Molton Brown supplies make this your luxe country getaway. Now with unlimited WiFi. The perfect getaway for one to three couples, Hawthorne offers multiple rooms and lots of space for maximum relaxation and taking in the country. >> Enjoy the view from the sun-drenched front porch. >> Nap on the big L-shaped sofa in the living room. The two extra deep Restoration Hardware couches are 7’ long; they also serve as larger than usual single beds >> Cozy up with a book by the fieldstone fireplace in the fully screened back porch (with glass panels in Fall and Winter). >> Share sunset cocktails in the Adirondack chairs up in the field overlooking the valley. >> Cook in the well-equipped kitchen. >> Eat your candle-lit dinner in the dining room overlooking the valley. This is a fully equipped country farmhouse, with Watson Kennedy goods throughout the home. Professional design, high quality kitchen equipment and accoutrement, linens, blankets and comforters, and Malin+Goetz bath supplies make this your luxe country getaway. You will be the only guests in the house, with no one else on-site. Lots of hiking in the valley and nearby conservancy areas, biking on country roads, cross-country, downhill or snowshoe during the snowy months, or take in all the antique shops and history year-round. This peaceful property is minutes from the Hawthorne Valley Farm store, 20 minutes to the world-class food and vintage mecca of Hudson, and 30 minutes from the culture and history of Tanglewood, Jacobs PIllow and the Berkshires. For recreation there is hiking in the valley and nearby conservancy areas, biking on country roads, or cross-country, downhill or snowshoeing during the snowy months. Hawthorne is a 2-hour drive from NYC or a 2-hour Amtrak ride from Penn Station to Hudson, and then a 20 minute drive by car or taxi. The house is conveniently close to the Taconic Parkway, while set in a peaceful and quiet valley.

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!

Cheerful Catskill Village Cottage

Bright and airy Catskill village refuge - a wildflower and wildlife haven in the thick of things. Historic house set on a quarter acre of trees and wildflowers, but blocks from Main Street, Catskill. Walk to Foreland, The Lumberyard, the incredible village cemetery, Thomas Cole House, restaurants and shops. Olana State Historic Site is right across the bridge! Cottage has a full kitchen, clawfoot tub, penny tile shower, front porch, dining room and large living room. Truly peaceful and lovely.

Sugar Shack | Romantic Tiny Home + Hot Tub

Sugar Shack | Romantic Tiny Home + Hot Tub. Celebrate Valentine’s all of FEB with complimentary roses-prosecco-robes-slippers! 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.

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.

The Writer's Cottage

The Writer's Cottage is a tiny white house on a country road; vintage, complete, and inspiring. Built in the nineteenth century, it's perfect for a solo traveler or a pair of travelers exploring the Berkshires and the Hudson Valley. If you like rustic buildings, you'll be a fan of the cottage; it's an incredibly cozy time warp. Queen bed and living quarters downstairs; airy loft up a narrow set of enclosed stairs. There's an orchard and lawn with grill, hammock and ironwork table.

The Hobbit House at June Farms

Watch June Farms on Amazon Prime Video! Enjoy 120-acres of beautiful farmland while you stay in your very own Hobbit house! Nestled in the hills of Hudson Valley, June Farms is a gorgeous animal sanctuary. During your stay, you will be able to meet our Shire horses, Highland cows, spotted pigs, Nigerian dwarf goats, many chickens and ducks! From June 1 - Labor Day, the bar & restaurant is open most days for you to enjoy (check our calendar to be sure). We look forward to meeting you!

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!

Large bohemian loft: The Chromium Compound

Large storefront converted to colorful open plan apartment in the heart of downtown Troy. Blocks away from RPI, and steps away from most of Troy's nightlife. Warning: this urban bohemian experience may bring back memories of Williamsburg Brooklyn or Downtown LA in the 90's. Note that sounds from outside and adjacent apartments may bother light sleepers, so don't book this one if that is a concern for you. Also parties are not allowed because of close neighbors! Thanks!

Tiny House, Big Adventure; 20 min to Skiing

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.

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.

Berkshire’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.