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 5.072.620 ₫ per night from 1 Jun to 2 Jun
5.072.620 ₫
5.666.241 ₫ total
1 Jun - 2 Jun
includes taxes & fees
9.8/10 Exceptional! (50 reviews)
"My favorite place to stay! Always comfortable and breakfast was great."
Reviewed on 29 May 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is 3.200.582 ₫ per night from 2 Jun to 3 Jun
3.200.582 ₫
4.162.882 ₫ total
2 Jun - 3 Jun
includes taxes & fees
9/10 Wonderful! (960 reviews)
"Hot tub doesn’t go above 95 which is colder than you think, didn’t have any luggage carts available after asking 3 different people, but it’s a charming place to end on a positive note"
Reviewed on 28 May 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is 2.822.818 ₫ per night from 7 Jun to 8 Jun
2.822.818 ₫
3.153.087 ₫ total
7 Jun - 8 Jun
includes taxes & fees
9/10 Wonderful! (964 reviews)
"The converted motel has several appealing features — it was clean, the Le Labo products smelled wonderful, and the lobby bar is beautifully designed. Unfortunately, the level of service fell well below expectations. Two days before our arrival, I received a survey asking whether we’d like any additional ..."
Reviewed on 27 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.
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.
