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 HK$1,285 per night from 1 Nov to 2 Nov
HK$1,285
HK$1,436 total
1 Nov - 2 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
Antique Farmhouse Totally Restored

Antique Farmhouse Totally Restored

Sheffield MA
Stay at this family-friendly holiday home in Sheffield. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Mount Riga State Park and Taconic ...
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Antique Farmhouse Totally Restored
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is HK$649 per night from 9 Nov to 10 Nov
HK$649
HK$900 total
9 Nov - 10 Nov
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 ...
9/10 Wonderful! (1,239 reviews)
"Clean and comfortable"

Reviewed on 28 Oct 2026

Berkshire Mountain Lodge
See all 1,305 properties in Sheffield
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.
Antique Farmhouse Totally Restored

Antique Farmhouse Totally Restored

Sheffield MA
Stay at this family-friendly holiday home in Sheffield. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Mount Riga State Park and Taconic ...
Antique Farmhouse Totally Restored
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 ...
9/10 Wonderful! (1,239 reviews)
"Clean and comfortable"

Reviewed on 28 Oct 2026

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! (156 reviews)
"We were amazed of the space of the villa and plenty of parking, staff handled our check-in with professionalism and how the property was well maintained beautifully."

Reviewed on 19 Oct 2026

The Ponds at Foxhollow
See all properties in Sheffield
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

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.
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A row of parked cars along a street lined with brick buildings, including a sign for 'Vault Studio' and 'Hotpoint'.

Great Barrington

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