Sheffield, MA

Travel Guide

Sheffield
Photo by Kim Knox Beckius
Photo by Kim Knox Beckius
Wilder House Berkshires

Wilder House Berkshires

2 out of 5
48 S Main Street, Sheffield, MA
The price is ￥28,321 per night from Oct 8 to Oct 9
￥28,321
￥31,635 total
Oct 8 - Oct 9
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 ...
9.6/10 Exceptional! (32 reviews)
"Beautiful and very comfortable house. Our hosts were always friendly and accessible, breakfast was delicious!"

Reviewed on Aug 30, 2025

Wilder House Berkshires
Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County

Sheffield
The price is ￥54,468 per night from Sep 28 to Sep 29
￥54,468
￥101,731 total
Sep 28 - Sep 29
includes taxes & fees
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! (9 reviews)
"This was exactly what we were looking for. The property was magnificent the cabin cozy, fully stocked. We plan on coming back soon."

Reviewed on Aug 27, 2025

Guesthouse Cabin vacation rentals in Berkshire County
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
The price is ￥13,757 per night from Sep 28 to Sep 29
￥13,757
￥18,665 total
Sep 28 - Sep 29
includes taxes & fees
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (646 reviews)
"Excellent location. Friendly staff."

Reviewed on Sep 17, 2025

Berkshire Mountain Lodge
See all 1,251 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.
Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County

Sheffield
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! (9 reviews)
"This was exactly what we were looking for. The property was magnificent the cabin cozy, fully stocked. We plan on coming back soon."

Reviewed on Aug 27, 2025

Guesthouse Cabin vacation rentals in Berkshire County
Antique Farmhouse Totally Restored

Antique Farmhouse Totally Restored

Sheffield
Book a stay at this family-friendly vacation home in Sheffield. Enjoy free WiFi, a water park, and a fitness center. Popular attractions Mount Riga State Park ...
9.8/10 Exceptional! (58 reviews)
"The property was beautiful. Very spacious, inside and out."

Reviewed on Aug 17, 2025

Antique Farmhouse Totally Restored
The Race Mountain House

The Race Mountain House

2 out of 5
Sheffield
Stay at this vacation home in Sheffield. Enjoy laundry facilities, patios, and in-room fireplaces. Popular attractions Mount Everett State Reservation and Drury ...
10/10 Exceptional! (3 reviews)
"This is a very special place, with lots of space, comfortable beds, and many many comfortable places to sit and hang out.Check in was a non-issue. The kitchen was well equipped"

Reviewed on Aug 18, 2025

The Race Mountain House
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 travels 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 with a trip to Ashley House. Discover the area's breweries or seek out the hiking trails.

Ashley House

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

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

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