Sheffield

Travel Guide

A lakeside town with autumn foliage, a bridge, and a rocky shoreline.
A covered wooden structure with a sloped roof, surrounded by greenery and trees.
A wooden covered bridge with a gabled roof, surrounded by trees and a body of water.
Wilder House Berkshires

Wilder House Berkshires

2 out of 5
48 S Main Street Sheffield MA
The price is P10,315 per night from Nov 15 to Nov 16
P10,315
P11,521 total
Nov 15 - Nov 16
includes taxes & fees
Stay at this B&B in Sheffield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife ...
9.8/10 Exceptional! (72 reviews)
"Clean, cozy, and charming. The breakfast is delicious and all went smoothly."

Reviewed on Oct 19, 2026

Wilder House Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is P4,832 per night from Dec 6 to Dec 7
P4,832
P6,803 total
Dec 6 - Dec 7
includes taxes & fees
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
Berkshire Mountain Lodge
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
The price is P7,931 per night from Dec 12 to Dec 13
P7,931
P8,859 total
Dec 12 - Dec 13
includes taxes & fees
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
The Yankee Inn
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.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
Berkshire Mountain Lodge
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7 Lenox MA
Stay at this aparthotel in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and The Mount are located ...
8.4/10 Very Good! (157 reviews)
"liked it was clean . furniture is dated. Roads need repair . too many potholes"

Reviewed on Nov 2, 2026

The Ponds at Foxhollow
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.

Stay near popular Sheffield attractions