Photo by Elizabeth Massa Peroulakis

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Compare 4 Chalets in Chester with updated reviews, rates, and availability.

"We were all very rested and relaxed. We enjoyed the beautiful spaces to sit and enjoy each other’s company. The chalet, flowers and setting made a terrific base to come and go from as we celebrated a family wedding."

"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. "

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

garden view of the back of the cabin, with the deck

"We really enjoyed our stay at this adorable A frame home. The home was a quick drive to tanglewood and the views were beautiful. The owner was very communicative and prompt with answering any questions. "

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Other property types in Chester

Chester Vacation Rental | 2BR | 1BA | 2,000 Sq Ft | Stairs Required

"The stay at the property was enjoyable. The space was large, spacious and very clean. Two people were able to stay quite comfortably."

"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "

AED 821 total

includes taxes & fees

30 Dec - 31 Dec

"My family and I really enjoyed our stay at the lake. My kids enjoyed playing outside in the snow. We had such a quality family time playing board games, watching movies and drinking hot cocoa. Justin was such a great host and really helpful when needed. We’re definitely coming back!"