Sheffield Travel Guide

Tourist 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
Fully refundableReserve now, pay when you stay
The price is £138 per night from 10 Sept to 11 Sept
£138
10 Sept - 11 Sept
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 ...
9.6/10 Exceptional! (29 reviews)
"Brads and Lara both served a fabulous breakfast. So friendly and welcoming! The bed was very comfortable. Only complaint was that the cabinet, closet door needs to be greased with WD 40 please on the hinges! A terrible & loud screeching noise!"

Reviewed on 12 Aug 2025

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 water park and a fitness centre. Popular attractions Mount Riga State Park and Taconic ...
9.8/10 Exceptional! (56 reviews)
"It was a fun place for a lot of people to stay. The only negative was the owner not having the air conditioning units in the windows of the bedrooms especially since it was so hot."

Reviewed on 14 Jul 2025

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Antique Farmhouse Totally Restored
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Stay at this 3-star 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 ...
8.8/10 Excellent! (561 reviews)
Rest, relax, and repeat
"Great value for families! The welcoming staff, location (Lenox/Pittsfield border), spacious suite, and ample amenities made for a fantastic vacation. No free breakfast but there are several dining options and markets nearby. Gorgeous view of the sunset from the upper floors. There was a note of upcoming ..."

Reviewed on 14 Aug 2025

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Berkshire Mountain Lodge
See all 1,257 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.
The Race Mountain House

The Race Mountain House

2 out of 5
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 ...
10/10 Exceptional! (2 reviews)
Extended family getaway
"This trip was for our extended family including 10 people ages 18-??. This house is located about 1/2 mile up a windy road above the race brook lodge's main facilities. Everyone loved the secluded location with beautiful views of the mountains out of main living area and 2nd floor. There were so ..."

Reviewed on 7 Jul 2025

The Race Mountain House
Antique Farmhouse Totally Restored

Antique Farmhouse Totally Restored

Sheffield, MA
Stay at this family-friendly holiday home in Sheffield. Enjoy free Wi-Fi, a water park and a fitness centre. Popular attractions Mount Riga State Park and Taconic ...
9.8/10 Exceptional! (56 reviews)
"It was a fun place for a lot of people to stay. The only negative was the owner not having the air conditioning units in the windows of the bedrooms especially since it was so hot."

Reviewed on 14 Jul 2025

Antique Farmhouse Totally Restored
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! (7 reviews)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space."

Reviewed on 12 Aug 2025

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

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