Find Family Hotels in Sheffield, MA

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Sheffield Family Hotels

This weekend
Next weekend

Top Sheffield Family Hotels

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Beautiful location!"
The price is NT$3,796
NT$4,240 total
includes taxes & fees
Sep 1 - Sep 2
The Black Swan Lee - Lenox, Ascend Hotel Collection

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
7.4 out of 10, Good, (536)
"Run down old property , room smelled , dirty carpet "
The price is NT$2,958
NT$3,304 total
includes taxes & fees
Aug 3 - Aug 4
Travelodge by Wyndham Great Barrington Berkshires

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
10.0 out of 10, Exceptional, (4)
"Our stay was terrific, and we appreciated the staff's attentiveness, especially Anthony's."
The price is NT$4,815
NT$5,379 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express & Suites Pittsfield - Berkshires

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (615)
"It was a clean, well-run, low cost option. "
The price is NT$1,905
NT$2,128 total
includes taxes & fees
Aug 17 - Aug 18
Econo Lodge Lee - Great Barrington

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (723)
"No complaints at all. Great place to stay!"
The price is NT$4,512
NT$5,040 total
includes taxes & fees
Aug 27 - Aug 28
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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.

Top Sheffield Hotel Reviews

Frequently asked questions

What's Sheffield like for family-friendly vacations?
If you've been thinking about a trip with your kids, the historic destination of Sheffield is a good choice. The local tours here makes this a great vacation spot for families. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 22 mi (35.4 km) from the city center.
When's the best time to book a family-friendly vacation in Sheffield?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Sheffield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's there to see and do with your family in Sheffield?
While you are visiting Sheffield, you might want to round up the kiddos and make time to see interesting attractions such as Mount Everett State Reservation, Ski Butternut, and Mahaiwe Performing Arts Center. Make sure you have lots of time for activities like Catamount Ski Area and Infinity Music Hall and Bistro.