What Guests Are Saying About Their Berkshires Stay
“if there was a rating higher than a 5/5 i would leave it. every detail of this house brings joy, warmth, and comfort. for a group that likes to cook and play games, i’m not sure i’ve ever been in a better spot with more amenities: the pizza oven, the kitchen packed with appliances, swings, games, and more. it was my 30th birthday but graybarn provided me such childlike whimsy.”
“This was my second time staying in this home and we had a great time! The house was well equipped for our group of 8 and the views of the fall foliage were beautiful. The host was extremely responsive and helpful when we had any questions during our stay.”
“We escaped the city with a few friends and this place was amazing! Very well stocked and beautiful design, would definitely recommend!”
“Our stay at Doodletown was incredible! The perfect peaceful mountain retreat. Incredible great room and open living spaces. Would happily return and recommend!”
“This house was really nice for a relaxing week away from home. The kitchen is well stocked with pots, pans, etc. so we could cook anything we wanted. We loved the steam shower and heated floors in the primary bath too. The area has some cute farm stores and co-ops that were fun to explore.”
“Wow! What a beautiful peaceful spot! We had such a great weekend. Thank you!”
Discover New Marlborough
Set across hill towns, farm fields, and hardwood forest in the southern Berkshires, New Marlborough is the slow-paced base for everything the region is known for, from waterfall hikes and lake mornings to long dinners, quiet bookstores, and a real Tanglewood night. Most of it is within thirty minutes of the front door.
The southern Berkshires are stacked with trail options that suit a half-day plan or a longer push. Bash Bish Falls, Massachusetts’s tallest single-drop waterfall, is the iconic stop, with a short out-and-back from the lower lot or a longer route in from Mount Washington State Forest. For ridge views, Mount Everett rewards a steeper climb with the kind of summit reset that makes the rest of the day feel easier. Race Brook Falls and Sage’s Ravine add quieter, less-trafficked alternatives, and York Lake is a calm spot for a swim or paddle when the trails are busy. Most of our New Marlborough homes put you within fifteen to twenty-five minutes of a trailhead, so a full morning on the trail still ends with a proper kitchen and a place to put your feet up.
When the snow lands, the southern Berkshires turn into a low-key ski region with short lift lines and an easy weekend rhythm. Catamount sits right on the New York/Massachusetts line, with 37 trails, night skiing on Fridays and Saturdays, and a lively summer-and-fall lineup of zip lines and aerial adventures off-season. Closer to Great Barrington, Ski Butternut is the classic family hill with wide cruisers and a real teaching mountain feel. Otis Ridge rounds out the local options for quick sessions or a kid’s first day. For deeper context, see our places to stay near Catamount Mountain if you’re planning a ski-first weekend.
New Marlborough’s village centers, Mill River, Southfield, and Hartsville, are the kind of stops where one good coffee and a porch chair can carry a whole morning. From there, Great Barrington is the closest hub, with bookstores, indie cafes, a strong restaurant lineup, and a steady weekend calendar of music and markets. Sheffield is the antiques capital of the Berkshires for a reason, with shops worth a slow afternoon. Stockbridge has the polished Main Street feel that inspired Norman Rockwell, and Lenox brings the Tanglewood crowd in summer. If you’re staying with us, the closest meaningful town is usually a fifteen-minute drive, and a town-hop loop is easy to build in a single day.
Summer in the southern Berkshires has a soundtrack, and a Tanglewood night is the local rite of passage. Lawn tickets are the move: bring a blanket, a real dinner, and a good bottle, and you have an evening worth driving for. Beyond Tanglewood, the Norman Rockwell Museum in Stockbridge is the rare museum that lives up to its postcard, and Berkshire Theatre Group runs a strong summer season across the Fitzpatrick Main Stage in Stockbridge and the Colonial Theatre in Pittsfield. If you want a bigger swing, MASS MoCA up in North Adams is about an hour and worth the day. Lenox is closest to Tanglewood, but our New Marlborough homes put you within about forty-five minutes of the lawn.
The Old Inn on the Green, just down the road on the Hartsville-New Marlborough Road, is the destination dinner that anchors the town’s food reputation, with a tasting menu and a candlelit dining room worth booking ahead. For a casual everyday breakfast and a sandwich worth driving for, the Southfield Store is the local move. Around Great Barrington, The Prairie Whale is a solid post-hike dinner and Marketplace Kitchen Café handles a fast, good lunch. John Andrews Farmhouse Restaurant in South Egremont rounds out the higher-end options. Or skip the reservation entirely, stock up at the farmers’ market, and cook in your rental’s kitchen. Every Red Cottage home is set up for it.