Sheffield, MA Chalets

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Compare 4 Chalets in Sheffield 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. "

"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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Sunrise lights up the front of the house. Moon sets over the mountain.

"I'd describe the house as elegantly eclectic. The owner is clearly a collector of interesting items which they arrange in a way that enhance (rather than potentially clutter) the interior. The kitchen and living spaces are open and easy to mingle around. The four bedrooms and three bathrooms easily and comfortably accommodated two couples and two singles. Our stay could not have been better! "

"We stayed at this home about the same time last year and we were so happy with everything about it, we jumped at the opportunity to stay there again. The house has absolutely everything you'd need and is close to Canaan, CT and Great Barrington, MA and everything the Bershires have to offer. Sabrina is a great host and responded within minutes to any questions I had. We HIGHLY recommend this home."

AED 1,863 total

includes taxes & fees

5 Jan - 6 January 2025

"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!"

Recent reviews of Sheffield hotels

5/5 Excellent

"From the welcoming drinks, to the complimentary bottle of wine in the room, to the excellent breakfast, the Cornell Inn was a treat to stay at."

A verified traveler stayed at The Cornell Inn, Lenox

Posted 20 hours ago

The Black Swan Lee - Lenox, Ascend Hotel Collection

5/5 Excellent

Great affordable inn to experience the Berkshires!

"Very positive experience and good value for money. Not a “high end” inn - linens and towels are lower quality, no fancy toiletries , but very clean friendly place. Rooms a bit older and worn (chips in wood and doors etc) Loved the free breakfast - not just breads but also hard boiled eggs yogurts , many whole fruits in a nice breakfast room. Pretty location on a body of water. Nice views from room. Very short drive to downtown Lee , 10 min to Stockbridge "

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

Posted 1 day ago

5/5 Excellent

"went for a quick ski overnight. the motel was very clean, in good shape, quiet, pleasant check in/out experience, free coffee, everything in the room worked, the water was hot the pressure was good there was a fridge and microwave and blowdryer, comfy bed, plenty of hanging closet space, a little table and chair area by the front window, a nice view of the playground, good heating unit, and very convenient to everything you need and want to do here, and most of all affordable including my expedia discount. nice to get all of that at a great rate! ill be back"

A verified traveler stayed at Monument Mountain Motel

Posted 2 days ago