Search Chester Cottage Rentals from CA $207

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Browse Select Chester Cottages

Enjoy al fresco dining and socializing in this serene outdoor patio area surrounded by lush greenery and trees.

"Lovely place!"

CA $381 total

includes taxes & fees

Sep 3 - Sep 4

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!"

Relax in this inviting room with a plush bed, sofa, and TV, offering stunning views of Lake.

"Wally and Donna were very hospitable! We loved this cottage and its location to everything we wanted to do. The neighborhood was tranquil and beautiful. Such a great place!"

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."

Stylish single-story home with a gabled roof and a cozy front porch.

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."

Kitchen features a large window, refrigerator, stove, and dishwasher, with a ceiling fan for ventilation.

"Beautiful historical house in a rural setting. We were attending performances at Jacob’s Pillow. This house is approximately 20 minutes away, so very convenient."

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 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...