Sheffield

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
Fully refundableReserve now, pay when you stay
The price is €156 per night from 10 Sept to 11 Sept
€156
10 Sept - 11 Sept
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! (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
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 WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (590 reviews)
"Flexible dates, reasonable price, old but clean"

Reviewed on 24 Aug 2025

Get rates
Berkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is €154 per night from 21 Sept to 22 Sept
€154
21 Sept - 22 Sept
includes taxes & fees
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (693 reviews)
"We needed a place to stay in the area Found the place cutely decorated and was happy there was a restaurant on premise"

Reviewed on 21 Aug 2025

Berkshires Untold
See all 1,256 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
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! (57 reviews)
"The property was beautiful. Very spacious, inside and out."

Reviewed on 17 Aug 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)
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
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! (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
Great Barrington

Great Barrington