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 4.557.773 ₫ per night from 30 Oct to 31 Oct
4.557.773 ₫
5.091.032 ₫ total
30 Oct - 31 Oct
includes taxes & fees
9.6/10 Exceptional! (35 reviews)
"Highly recommend this beautiful bed & breakfast! The room was wonderful and overlooked the property, the breakfast was delicious, and the hospitality was amazing. I had a fantastic stay, and will definitely stay at The Wilder House again when I'm in the area."
Reviewed on 25 Sept 2025
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is 2.458.309 ₫ per night from 2 Nov to 3 Nov
2.458.309 ₫
3.335.171 ₫ total
2 Nov - 3 Nov
includes taxes & fees
8.8/10 Excellent! (668 reviews)
"Nice room, bathroom could use some repair, crumbling sheetrock surrounding tub enclosure, priced well"
Reviewed on 30 Sept 2025
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
Fully refundableReserve now, pay when you stay
The price is 3.062.254 ₫ per night from 2 Nov to 3 Nov
3.062.254 ₫
3.788.746 ₫ total
2 Nov - 3 Nov
includes taxes & fees
9/10 Wonderful! (744 reviews)
"Not all rooms are the same, some are not renovated"
Reviewed on 1 Oct 2025
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.
