Sheffield Travel Guide

Tourist Guide

FTYTP1 The Upper Sheffield Covered Bridge, Sheffield, Massachusetts, USA
Sheffield
Wilder House Berkshires

Wilder House Berkshires

2 out of 5
48 S Main Street Sheffield MA
The price is £133 per night from 20 May to 21 May
£133
20 May - 21 May
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! (48 reviews)
Very comfortable bed, that was mostly what I cared about. I got my beauty sleep)

Reviewed on 11 May 2026

Wilder House Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is £90 per night from 24 May to 25 May
£90
24 May - 25 May
includes taxes & fees
Stay at this golf lodge in Pittsfield. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff and the clean rooms in their ...
9/10 Wonderful! (934 reviews)
Clean and great job staffing

Reviewed on 15 May 2026

Berkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
The price is £96 per night from 28 May to 29 May
£96
28 May - 29 May
includes taxes & fees
Stay at this lodge in Lenox. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in their reviews. ...
9/10 Wonderful! (948 reviews)
All was good

Reviewed on 16 May 2026

Berkshires Untold
See all 1,301 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
The Race Mountain House

The Race Mountain House

Sheffield MA
Stay at this holiday home in Sheffield. Enjoy laundry facilities, patios and in-room fireplaces. Popular attractions Mount Everett State Reservation and Drury ...
9.6/10 Exceptional! (7 reviews)
We had a wonderful 2-day stay at this charming house! The location is perfect, nestled near the mountains with breathtaking views. The house itself is clean and cozy, with comfortable bedrooms stocked with extra blankets and pillows. The spacious bathrooms (both upstairs and downstairs!) had plenty ...

Reviewed on 3 Jan 2026

The Race Mountain House
Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County

Sheffield MA
Stay at this cabin in Sheffield. Enjoy a garden, patios and cable/satellite TV service. Popular attractions Mount Everett State Reservation and Plaintain Pond ...
10/10 Exceptional! (10 reviews)
We were a group of moms who snuck away for the night and this cabin was the perfect retreat. Well stocked and very cozy on a winter night. We had to leave very early the next morning to beat a snowstorm and the very long driveway was already sanded and we felt very safe. Lisette was great to work ...

Reviewed on 29 Jan 2026

Guesthouse Cabin vacation rentals in Berkshire County
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.

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.

Magnolia Bluffs Casino

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.

Ashley House

Lime Kiln Farm Wildlife Sanctuary

You can take time to visit Lime Kiln Farm Wildlife Sanctuary during your travels to Sheffield. Make some time to visit the casinos while you're in the area.

Lime Kiln Farm Wildlife Sanctuary

Bartholomew's Cobble

You can take time to visit Bartholomew's Cobble during your travels to Sheffield. Make some time to visit the casinos while you're in the area.

Bartholomew's Cobble

Drury Preserve

You can take time to visit Drury Preserve during your travels to Sheffield. Make some time to visit the casinos while you're in the area.

Drury Preserve

Bartholomews Cobble

Explore the great outdoors at Bartholomews Cobble, a lovely green space in Sheffield. Make some time to visit the casinos while you're in the area.

Bartholomews Cobble

Cities near Sheffield

Great Barrington

Great Barrington