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 4.238.311 ₫ per night from 16 Apr to 17 Apr
4.238.311 ₫
4.734.194 ₫ total
16 Apr - 17 Apr
includes taxes & fees
9.8/10 Exceptional! (44 reviews)
Only discomfort was a hard rug on my barefeet. So I'll remember to bring slippers. Otherwise, the ambiance, service, friendliness, access was wonderful. What a lovely place!
Reviewed on 3 Apr 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is 2.165.972 ₫ per night from 19 Apr to 20 Apr
2.165.972 ₫
3.007.781 ₫ total
19 Apr - 20 Apr
includes taxes & fees
9/10 Wonderful! (905 reviews)
Clean, hot shower. Great pressure
Reviewed on 14 Apr 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is 2.067.007 ₫ per night from 21 Apr to 22 Apr
2.067.007 ₫
2.308.847 ₫ total
21 Apr - 22 Apr
includes taxes & fees
9/10 Wonderful! (897 reviews)
For an old roadside motel they have turned this into the coziest little place. The library is charming, the rooms are cool and comfortable and the food was wonderful. Highly recommend
Reviewed on 15 Apr 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.
Popular places to visit
Magnolia Bluffs Casino
Why not roll the dice with a visit to Magnolia Bluffs Casino during your time in Sheffield? Discover the area's breweries or seek out the hiking trails.
Ashley House
You can learn about the history of Sheffield when you stop by Ashley House. Discover the area's breweries or seek out the hiking trails.
