Sheffield Packages (Flight + Hotel)
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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 ฿6,302 per night from 27 May to 28 May
฿6,302
฿7,039 total
27 May - 28 May
includes taxes & fees
9.8/10 Exceptional! (49 reviews)
"the breakfast is from heaven. the house is beautiful. love the stay."
Reviewed on 18 May 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is ฿2,868 per night from 24 May to 25 May
฿2,868
฿3,933 total
24 May - 25 May
includes taxes & fees
9/10 Wonderful! (942 reviews)
"the Kitchen appeared to be fully equiped. The only cpmplaint I have was there were no avaiable plugs for mt CPAP machine nect to the bed> Easy fix is to offit the room with a multi plug on the night table.or lamp with plugs. Also there were no USB charging ports. Otherwise the facility was great"
Reviewed on 19 May 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is ฿4,082 per night from 25 May to 26 May
฿4,082
฿4,559 total
25 May - 26 May
includes taxes & fees
9/10 Wonderful! (952 reviews)
"all very good for our 1 night stay!!"
Reviewed on 20 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.
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
