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

"The location was great. Very peaceful. Not far from Lee, Lenox or Great Barrington. The house was very cute and as described. Will absolutely stay again. "

"Enjoyed the quietness and spaciousness of the house and property. Fully equipped kitchen and multiple seating areas allowed our multi generational family to have the comforts of home during our visit. No problems were encountered and we highly recommend this property to families."

3 bedrooms, desk, iron/ironing board, travel crib

"Short couples getaway to recharge. The house was perfect and the wood stove kept the house toasty through the cold windy stay. HINT: coming from NY/NJ, buy your groceries as you pass through Great Barrington and save that extra trip."

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Recent reviews of Pittsfield hotels

Best Western Plus Berkshire Hills Inn & Suites

5/5 Excellent

"Very friendly staff. Greeted each time, coming in or going out. Breakfast was good, many varieties available, came with stay. Make your own waffles! Maybe I'm new to staying at Inns, motels, etc., as much as I have this year, but that was a pleasant surprise."

A verified traveler stayed at Best Western Plus Berkshire Hills Inn & Suites

Posted 2 days ago

The Black Swan Lee - Lenox, Ascend Hotel Collection

5/5 Excellent

Oh oh New England!

"The Black Swan is a reliable stay. If you are passing through, get the cheaper rooms on the parking lot side, if you are staying for a few nights get a room with a lake view and balcony. Not a chain!"

A verified traveler stayed at The Black Swan Lee - Lenox, Ascend Hotel Collection

Posted 2 days ago