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
9.8/10 Exceptional! (41 reviews)
The place is lovely, room is cozy, and the bed is comfy
Reviewed on 22 Dec 2025
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is 2.656.806 ₫ per night from 21 Jan to 22 Jan
2.656.806 ₫
2.967.652 ₫ total
21 Jan - 22 Jan
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
Everything was great!
Reviewed on 8 Jan 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is 2.592.356 ₫ per night from 1 Feb to 2 Feb
2.592.356 ₫
3.482.511 ₫ total
1 Feb - 2 Feb
includes taxes & fees
9/10 Wonderful! (810 reviews)
Very comfortable and very close to ski slope and restaurants
Reviewed on 10 Jan 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.
