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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!

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.

Cantabile life in the Berkshires

Relax with your family and friends after a day of skiing, hiking or a night of Tanglewood concert in this newly renovated home at the center of the Berkshires. Located in a quiet and friendly neighborhood, our home is 5min to Pontoosuc Lake and Lake Onota, 10min to Bousquet, 15min to Mt Greylock, 20min to Jiminy Peak and Tanglewood. Multiple grocery stores and shopping centers near by. Child/baby friendly, we have books, games, PingPong, foosball and a grand piano. Musicians are welcome!

Hidden Oasis in the Mountains by Evergreen Home

Evergreen Home Vacation Rentals invites you to this hidden oasis in the heart of the Berkshires. This attractive 5-bedroom home features a large, fully-outfitted kitchen, Tuft & Needle mattresses, and stunning mountain views. Relax in the hot tub, enjoy the perennial gardens, or gather on the stone patio by the fire pit. Just 7 minutes to Bousquet Mountain and minutes from Lenox and Tanglewood, this is the perfect retreat for family and friends. Experience luxury and comfort—book today!

Beautiful Lake-view Getaway!

Enjoy a weekend away in the heart of The Berkshires! Take in the stunning lake views and beautiful sunsets year-round. Whether you are looking for a lake getaway or Berkshires retreat in the summer, or a place to cozy up after a long day of skiing in the winter, my home will offer all the comforts you need to enjoy your time in The Berkshires. Enjoy the lake views from the hot tub (additional fee), sit around the fire pit and watch the sun set, or enjoy a home cooked meal on the patio!

Mid-Century At Friendly Hills w Guest Passes !

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

Comfy Quaint Tavern

Experience this beautifully renovated unit which is available for overnight guests. Enjoy the charm of yesteryear and the echo of laughter and friendship. This property was originally a tavern that opened in 1933 and received one of the first liquor licenses in the area after prohibition was repealed. Now a fully renovated one bedroom unit (within two-unit property) with so much of the historic charm restored for your recreation and relaxation. Off street parking.

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 Sunset House

Enjoy a getaway in the beautiful Berkshires! Our cozy home is on a quiet dead end street with a 3 minute walk to Pontoosic Lake. Centrally located, a 15 minute drive to Jiminy Peak Mountain Resort, 15 minutes to Bousquet Mountain Ski Area, a 25 minute drive to the famous Tanglewood or Naumkeag. The home is equipped with all basic needs, washer/dryer, smart TV's in living room and bedroom, WIFI included. 1 potty trained dog is welcome per stay.