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Compare 5 Chalets in Pittsfield with updated reviews, rates, and availability.

"My husband, dog and I had a Monday-Friday stay at Jaclyn's house on the water. We wanted a place that felt private but wasn't far from grocery stores, restaurants, and hiking. This place delivered! We did go out for a paddle on the little pond and saw some little fish and freshwater clam shells broken by a hungry creature. The swimming area is a 5 minute walk from the house. I sat out by the water to read in the shade and the sitting area is lovely and there were no bugs. They seem to spray the...

"Beautiful well kept house in the Berkshires, great view and layout. Close to amazing nature and Great Barrington if you need anything. Wonderful trip!"

Rustic contemporary with field stone foyer and working fireplace

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Other property types in Pittsfield

"We enjoyed our week in Pittsfield and at this home. The house was as described and expected, and it offered the privacy and seclusion we wanted. At the same time, the house is very conveniently located, and activities, beautiful walking trails, and restaurant options were nearby. We very much appreciated the reliable WiFi as some of our party had to work remotely during the week. Also, our pup loved the fenced in yard, the deck is great, and we enjoyed use of the fire pit. Would return again if...

"The property was perfect. Nice clean bedrooms with enough clean bathrooms for everyone. Beautiful full kitchen for meals. My 10 grandchildren enjoy the open space to run and play with each other, while the adult watch from the deck. At night we all enjoyed relaxing in the hot tub or sitting around the fire pit. I would highly recommend this place. "

AED 3,853 total

includes taxes & fees

1 Oct - 2 Oct

" We enjoyed our stay at Vacation Villa and the condo was extremely spacious and comfortable. The only complaint is the very soft bed. Upon check- in we were told we were 15 minutes early and had to stand in another line to wait to get a different room that would be ready at 3:45. Since we are gold members of hotel.com we always ask for a room upgrade and the manager seemed annoyed that we even asked for a room upgrade as well as arriving 15 minutes early and the greeting from all of the...

AED 717 total

includes taxes & fees

29 Sep - 30 Sep

Recent reviews of Pittsfield hotels

5/5 Excellent

"This hotel is immaculate. We were pleasantly surprised to have room cleaning each day of our stay. The staff is super friendly and efficient. One small disadvantage, the noise from the street traffic was loud in our room. We would definitely stay there again."

A verified traveler stayed at Hotel Downstreet

Posted 1 day ago

5/5 Excellent

Ny new favorite hotel in the Berkshires !

"Woa, this place is nice ! It used to be a motel, but do NOT deter you. Everything was impeccable and gorgeous. I ate breakfast and dinner at the restaurant and sat on the patio for a couple hours reading. Everything was just lovely ! Beautiful garden style patio with comfortable furniture. Elegant rooms and bathroom. This is almost like a small resort getaway. I will always stay here when I come to the Berks !!"

A verified traveler stayed at Life House Berkshires

Posted 3 days ago