Search Pittsfield Cottage Rentals from CA $1,672

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Browse Select Pittsfield Cottages

Enjoy a serene atmosphere with a view of lush greenery from the large window, and dine in style at the set table for two.

"Cozy, serene and bucolic waterfront hideaway within driving distance of Tanglewood, Shakespeare & Company, Jacob's Pillow and all the wonderful food and cultural Berkshire gems! Julie and Russ were amazing hosts. Great communication and wonderful restaurant and museum suggestions. Definitely planning another long weekend retreat!"

"Home our mother's 83rd birthday party cookout at the lake house with a few family members and it was a great day. Everyone loved the house. We enjoyed the stay"

Surrounded by tall trees, this cozy cabin offers a peaceful retreat in a natural setting.

"My husband, dog and I enjoyed a long weekend here to celebrate our 8th wedding anniversary- the property was beautiful and quaint! Perfect for exploring on walks, or nearby to the Norman Rockwell museum. Would stay here again."

Surrounded by a serene lawn and a tranquil pond, this peaceful setting offers a serene escape.

"Wonderful getaway, lovely hosts, great location, overall a fabulous place to relax and recharge. "

Stroll through the serene garden, surrounded by vibrant flowers and lush greenery, with a charming house in the background.

"We had a great stay- no complaints! Very close to Jiminy Peak, where we were skiing, and the house was very comfortable. Thank you!"

Sit by the lake and enjoy a serene moment with a cup on the dock.

"We stayed with family and friends and loved all of the offerings from the dock, fire pit and quiet neighborhood."

Relax in this cabin's open-plan living area with a fireplace, scenic lake views, and comfortable seating.

"We had a great time. The owner Bill was a great host."

Cozy interior with a brick fireplace, wooden ceiling, and a panelled wall.

"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."

Relax in this inviting living room with a plush sofa, a statement rug, and a tall floor lamp.

"The cottage was clean and as described. The street was very quiet."

Enjoy cooking in this well-equipped kitchen with a central island, dishwasher, stove, and refrigerator.

"Lovely lake house at the end of a long private road, perfect for a quiet getaway, close to all kinds of hiking and other natural attractions. Our hosts were super friendly and responsive. Highly recommended."

Relax by the pool surrounded by lush greenery and comfortable outdoor furniture.

"The house was very convenient to anywhere we wanted to go. We even had 5 deer welcome us the first night. House was very comfortable and we loved it."

Relax in a peaceful room with large windows overlooking the surrounding trees, a perfect spot for socializing and taking in the views.

"A short getaway with family. "

Enjoy the serene surroundings and well-maintained deck adjacent to this house.

"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...