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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!

Net Zero home with rustic Berkshire charm

Be a part of the solution in our centrally located solar home that sits on a safe and quiet street just a walk, ride, or drive from downtown Pittsfield! Warm up your day on the screened-in sun porch. Warm up your toes on the heated tile floors! Enjoy custom concrete counters and wood floors in this open kitchen concept. Grill out on the rear patio while your dogs roam in the enclosed backyard. Hiking trails abound and playgrounds are just a stroll away. We are emissions free! How cool is that?!

Dancing Horse Lodge

Dancing Horse Lodge is located in the heart of the Berkshire Mountains in Pittsfield, MA, minutes from Tanglewood, Barrington Stage, Jacobs Pillow Ballet, Kripalu Yoga, Shakespeare and Co. and skiing at Bosquet and Jiminy Peak. It is a light and bright residence located on a 20-acre horse farm with nature views out of each window. It is surrounded by miles of woods, great for hiking and cross country skiing. Close to all amenities yet affords beautiful, quiet country living. Come and enjoy!

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

Welcome to our little slice of heaven upstate. Located just a 5-minute drive to the MA border, a stay at our home in Canaan, NY means access to the best of both Columbia County and the Berkshires. In the summer, enjoy the private Adams Point Beach on Queechy Lake and easy access to Tanglewood. In the winter, explore 4 different local ski resorts and curl up by the cozy wood stove. In between, enjoy the peaceful pond views and secluded location on a dirt road. We can't wait to welcome you!

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.

King Bed |Wi-Fi| 2m to Ski Resort

Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. * 1.5 miles to Downtown * 1.3 miles to Mahaiwe Performing Arts Center * 44 miles to Albany International Airport *4.5 miles to Great Barrington Airport KEY FEATURES: *MCM Design * Plush King Sized Bed w/ high end Centium Satin Linens *High Speed Internet *58" TV w/ Hulu + Live

20 minutes to Jiminy Peak and Bousquet

This property is like nothing you've ever seen--a gem near the top of Mt. Lebanon with 75 acres of forest, streams, waterfalls, gardens, and historic ruins on a former Shaker settlement. The newly renovated Caretaker's Cottage has 2 bedrooms, kitchen, living room, and bathroom. The Taconic and Berkshire mountains stretch out before the deck and screened-in porch. Berkshire and Hudson Valley restaurants, shops, and entertainment are all nearby. Owners on site if you need them.

Friendly Hills | Passive Home • EV Charger

Welcome to Friendly Hills, a one-of-a-kind Mid-Century home nestled on 6 private acres. Built in the 1950s by GE engineer Willard F.M. Gray, this passive solar retreat offers panoramic views, triple-pane windows, and ceramic tile floors that retain heat year-round. Enjoy direct access to private hiking trails, peaceful ponds, and nearby Hancock Shaker Village. Fast Wi-Fi, thoughtful design, and natural beauty make this perfect for families, couples, and nature lovers alike.

Comfortable Pittsfield Loft

Located in the center of the Berkshires, this newly renovated Pittsfield apartment is comfortable and convenient. Come enjoy the new kitchen and delightful walk in shower. Centrally located to all of the wonderful Berkshires attractions this one bedroom apartment offers new appliances, driveway parking, washer and dryer. Yuhong and Mike live on-site in the apartment below and they are dedicated to providing an excellent guest experience. THIS IS A NO SMOKING APARTMENT

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.

Cozy cottage on peaceful pond

This little slice of heaven is located on the serene Richmond Pond. Right down the street from Balderdash winery and a 15 minute drive to charming downtown Lenox and Tanglewood. In Lenox you can find great dining, shopping, and there is plenty of hiking and biking around this area. This cozy cottage has everything you need for a Berkshire retreat. In the fall cozy up next to the fireplace inside or out take a break and unwind at this Peaceful oasis. 

Newly Renovated Red Door Annex

Private keypad entrance with parking. Large bedroom with a new Queen bed, full bathroom. There is a small table for dining and working, a small fridge, microwave, toaster oven, and pour-over coffee and tea in a nook outside the bedroom. The Annex is in a tranquil neighborhood between Great Barrington and Williamstown/North Adams and ski areas. 20 minutes to Lenox. Fire Pit. The Annex is attached to the main house but is completely private.