Sheffield Holidays
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Top hotels in Sheffield
Wilder House Berkshires
48 S Main Street Sheffield MA
Fully refundableReserve now, pay when you stay
The price is S$246 per night from 20 May to 21 May
S$246
20 May - 21 May
includes taxes & fees
9.8/10 Exceptional! (48 reviews)
Very comfortable bed, that was mostly what I cared about. I got my beauty sleep)
Reviewed on 11 May, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is S$154 per night from 24 May to 25 May
S$154
24 May - 25 May
includes taxes & fees
9/10 Wonderful! (932 reviews)
Loved this place - and would probably come. again. My only issue is that check-out is at 10:00 am. I had friends staying there who were not checking out, so I was able to linger in their suite. I imagine that I could have eaten breakfast in the large sunny open lounge on the first floor - if this ...
Reviewed on 14 May, 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is S$153 per night from 20 May to 21 May
S$153
20 May - 21 May
includes taxes & fees
9/10 Wonderful! (943 reviews)
Excellent bathroom and pleasant decor; very good value for the price for a midweek stay.
Reviewed on 15 May, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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