Holiday houses in 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.

Rustic Secluded Cabin near Berkshires. *wood stove

The Red House offers a peaceful secluded retreat, surrounded by acres of forest & with excellent hiking trails. Enjoy the tranquility of nature while being minutes from antiquing, Kripalu, the Norman Rockwell Museum, The Mount, Tanglewood, skiing, & Shakespeare & Co. You'll appreciate the serene privacy, situated on an old dirt road. Relax by the wood stove or in the sunroom. Nearby towns of Spencertown, Chatham, & West Stockbridge offer unique charm. 4WD vehicle is recommended for winter visits

A unique village home steps to shops, café, nature

This spacious four-bedroom, one-and-a-half-bath listing invites you to unwind in an old home full of character and warmth, with original features and vintage décor. Well stocked eco friendly provisions and fragrance/toxin free. Two dedicated workspaces with desks provide quiet areas for focused work. 10 minute walk to Main Street Chatham via sidewalk, enjoy nearby cafés, shops, and trails. An easy drive to the Berkshires, Hudson, or Albany, this house is truly one of a kind. Check in at 2pm.

Nordic Cabin - Light-Filled & Spacious with Firepi

Nordic Cabin is a mid-century, Scandinavian-inspired home on 6 acres of woods—just 2 hrs from NYC! Bright, light-filled spaces welcome you to unwind. The downstairs open plan design offers a spacious living room with a woodburning stove, a modern kitchen, dining table and a full bath. Upstairs, 3 bedrooms, a full bath, and a rec room with foosball. Outside, enjoy year-round beauty, dine under the stars, stay warm by the firepit, walk meandering trails or explore the nearby historic train line.

Romantic-Private-Western Tiny Cabin w/HOT TUB

Sept. SPECIAL (Mon-Thurs): Prosecco/s’mores kit/firepit supplies. Just 2.5 hours from NYC, escape to The Hitching Post—a romantic Western-inspired tiny home in Chatham, NY w/private hot tub, firepit, outdoor shower & rustic luxury throughout. Once the hideout of a legendary samurai cowboy, this unique retreat features a cozy queen bed nook, luxe bath & kitchenette. Just a 2-minute walk to Chatham’s restaurants, shops, brewery & theater. A perfect Hudson Valley getaway for couples. @artparkhomes

Walk to Main Chatham Villg Fully stocked Priv Park

WELCOME ALL. Pedestrian/Bike friendly Village home 200' to Main St pubs pizza Crandall, Yianni's, Bimi's fine & fun dining. PS21/McHaydn live theaters, shopping. Town park w/swim pond, free tennis courts w/in a mile. 12mi Hudson Amtrak (taxi, Uber avail). ArtOmi, Hawthorne Valley, Tanglewood near. Keyless entry. 100% smoke/pet-free property. Check-in 4pm/-out 11am. 2 laundromats w/in 1/2 mile. High-speed wifi & parking at door. Stocked home. Private outdoor dining w/propane bbq. 2 guests max.

Chatham Country Getaway

Highly rated, bright, open concept, two bedroom, one bath, duplex house. Conveniently located just one mile from Main St in Chatham between the Chatham Berry Farm and Mac-Haydn Theater. Just a 5 min drive from the TSP, a 10 minute drive to Art Omi, 20 min to Hudson about 35 to 40 minutes from Catamount Mountain, Bosquet, Jiminy Peak Ski Resort, Great Barrington, MA, and Tanglewood. Short term to semi long term stays are welcome and up to two pets may be allowed with prior approval from me.

Private Penthouse Apt in Historic Landmark 3-BR

Enjoy the privacy of this 3 bdrm apartment with the convenience of a charming, full-service restaurant just 2 flights down. This newly renovated space is located in a private section of the historic 'Chatham House', once a resort for artists & tourists of the Catskill Mountains. While the space & ease of a cozy tavern just below may incur some lazy, make sure you take a stroll to Main St.Chatham just steps away where you can shop, eat or even take in a movie. 20 min drive to Hudson Amtrak

Kinderhaus Loft in Chatham, New York

Kinderhaus Loft is on the 3rd floor accessed via an exterior stair case with a deck where you can enjoy views of the gardens & stars. There are lounge chairs and a grill for you to enjoy. The loft is in the center of the Village. You can walk to restaurants, shops, & the Crandall Theatre. You are within a mile of PS21 and MacHaydn Theater. You can also explore Hudson 12 miles away, Kinderhook 6 miles away & the Berkshires are 20-30 miles away. Close to hiking, skiing, theater & the arts.

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!

Monk's Bunk, Old Chatham

Forget your worries in this spacious and serene space. Tucked behind a large flowering hedge, Monk's Bunk is a rambling country home, surrounded by lawns, wildflowers and forest. Enjoy coffee on the back patio while listening to the brook and the birds. Stroll the forest path to Pinwheel Point overlook, or relax on the sunny front porch with a book. Haddock Hill Road is a cherished Dirt Road of Columbia County, and connects to the best hiking and biking in the Taconic Range

Luxury Barn Retreat Near Hudson & the Berkshires

Set on eight private acres where New York meets the Berkshires, this architect-designed 19th-century barn combines soaring ceilings, original beams and contemporary comforts. Enjoy a chef’s kitchen, two fireplaces, designer interiors, peaceful outdoor spaces and access to nearby Queechy Lake. A private outdoor sauna will be ready for all stays beginning October 1, 2026. Minutes from Chatham and an easy drive to Hudson, Great Barrington and Tanglewood.