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 S$234 per night from 12 Nov to 13 Nov
S$234
12 Nov - 13 Nov
includes taxes & fees
Stay at this B&B in Sheffield. Enjoy free breakfast, free Wi-Fi 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 19 Oct, 2026

Wilder House Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is S$138 per night from 6 Dec to 7 Dec
S$138
6 Dec - 7 Dec
includes taxes & fees
Stay at this golf aparthotel in Pittsfield. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff and the clean rooms in ...
Berkshire Mountain Lodge
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
The price is S$167 per night from 20 Nov to 21 Nov
S$167
20 Nov - 21 Nov
includes taxes & fees
Stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
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
Stay at this golf aparthotel in Pittsfield. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff and the clean rooms in ...
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 Wi-Fi, free parking and a fitness centre. 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 2 Nov, 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