Sheffield Holidays
Book a Hotel + Flight or Car together to unlock savings
Top hotels in Sheffield
Wilder House Berkshires
48 S Main Street Sheffield MA
Fully refundableReserve now, pay when you stay
The price is 5.023.461 ₫ per night from 2 Mar to 3 Mar
5.023.461 ₫
5.611.329 ₫ total
2 Mar - 3 Mar
includes taxes & fees
9.8/10 Exceptional! (43 reviews)
Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back.
Reviewed on 23 Jan 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is 2.970.221 ₫ per night from 2 Mar to 3 Mar
2.970.221 ₫
3.899.872 ₫ total
2 Mar - 3 Mar
includes taxes & fees
9/10 Wonderful! (865 reviews)
Overcharged and lied to said security deposit was released back but never was
Reviewed on 26 Feb 2026
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is 2.414.274 ₫ per night from 8 Mar to 9 Mar
2.414.274 ₫
2.696.744 ₫ total
8 Mar - 9 Mar
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
Room is attractive and clean and the staff is always welcoming. Back rooms, where we stay, are quiet and look out across a marsh to the mountain.
Reviewed on 28 Feb 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.
